NP-MRD: Showing NP-Card for Riboflavin (NP0000294)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:19:18 UTC

NP-MRD ID

NP0000294

Natural Product DOI

https://doi.org/10.57994/1703

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Riboflavin

Description

Riboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolizing of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin is found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. Riboflavin is yellow or orange-yellow in color and in addition to being used as a food coloring it is also used to fortify some foods. It can be found in baby foods, breakfast cereals, sauces, processed cheese, fruit drinks and vitamin-enriched milk products. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin adenine dinucleotide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652308122017442D          

 27 29  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16  3  1  0  0  0  0
 16  1  1  0  0  0  0
  4 10  1  0  0  0  0
 10  2  2  0  0  0  0
 11  1  2  0  0  0  0
  2  1  1  0  0  0  0
  2 12  1  0  0  0  0
 11  9  1  0  0  0  0
 12 15  1  0  0  0  0
 15  9  1  0  0  0  0
  5  3  2  0  0  0  0
  3  4  1  0  0  0  0
  6  4  2  0  0  0  0
  5  8  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  9 14  2  0  0  0  0
 12 13  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  1  0  0  0
 21 23  1  0  0  0  0
 21 24  1  6  0  0  0
 23 25  1  0  0  0  0
  8 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

HMDB0000244
     RDKit          3D
Riboflavin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5779   -2.3163    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.4736    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -0.1066    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.7205    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    2.0538    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    2.9100    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    4.2765    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    4.7839    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    5.0504   -0.1972 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    4.5229   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    5.3224   -1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    3.1986   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    2.3189   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855    0.9800   -0.4146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.5316   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.4044    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5609   -0.4759    1.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.2491   -0.3813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3146    0.3358    0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.9685   -1.2228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6592   -0.8027   -1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -2.2320   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.6276    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    0.1958   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.1649   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -1.9822    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -3.4574    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -3.3040    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -1.8007    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536   -2.3702    2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3092    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    6.0903   -0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3394   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.3501   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173    1.4581    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -0.1967    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675    1.1620   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    1.2301    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -1.0677   -1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.4424   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -3.0549   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -2.1329    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -3.0852    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -1.5688   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730   -3.9864    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -3.6599    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -3.8158   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  2  1  0
 24  4  2  0
 13  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  9 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  6
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
M  END

  Mrv1652308122017442D          

 27 29  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16  3  1  0  0  0  0
 16  1  1  0  0  0  0
  4 10  1  0  0  0  0
 10  2  2  0  0  0  0
 11  1  2  0  0  0  0
  2  1  1  0  0  0  0
  2 12  1  0  0  0  0
 11  9  1  0  0  0  0
 12 15  1  0  0  0  0
 15  9  1  0  0  0  0
  5  3  2  0  0  0  0
  3  4  1  0  0  0  0
  6  4  2  0  0  0  0
  5  8  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  9 14  2  0  0  0  0
 12 13  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  1  0  0  0
 21 23  1  0  0  0  0
 21 24  1  6  0  0  0
 23 25  1  0  0  0  0
  8 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1

> <INCHI_KEY>
AUNGANRZJHBGPY-SCRDCRAPSA-N

> <FORMULA>
C17H20N4O6

> <MOLECULAR_WEIGHT>
376.3639

> <EXACT_MASS>
376.138284392

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.50970932405913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-0.9165402600000004

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.852833299641368

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.969939364997856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.610702399953126

> <JCHEM_POLAR_SURFACE_AREA>
155.04999999999998

> <JCHEM_REFRACTIVITY>
96.2684

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
riboflavin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000244
     RDKit          3D
Riboflavin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5779   -2.3163    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.4736    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -0.1066    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.7205    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    2.0538    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    2.9100    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    4.2765    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    4.7839    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    5.0504   -0.1972 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    4.5229   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    5.3224   -1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    3.1986   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    2.3189   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855    0.9800   -0.4146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.5316   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.4044    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5609   -0.4759    1.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.2491   -0.3813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3146    0.3358    0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.9685   -1.2228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6592   -0.8027   -1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -2.2320   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.6276    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    0.1958   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.1649   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -1.9822    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -3.4574    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -3.3040    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -1.8007    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536   -2.3702    2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3092    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    6.0903   -0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3394   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.3501   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173    1.4581    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -0.1967    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675    1.1620   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    1.2301    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -1.0677   -1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.4424   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -3.0549   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -2.1329    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -3.0852    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -1.5688   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730   -3.9864    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -3.6599    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -3.8158   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  2  1  0
 24  4  2  0
 13  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  9 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  6
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
M  END

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
CONECT    1   16   11    2                                                  
CONECT    2   10    1   12                                                  
CONECT    3   16    5    4                                                  
CONECT    4   10    3    6                                                  
CONECT    5    3    8                                                       
CONECT    6    4    7                                                       
CONECT    7    8    6   27                                                  
CONECT    8    5    7   26                                                  
CONECT    9   11   15   14                                                  
CONECT   10    4    2                                                       
CONECT   11    1    9                                                       
CONECT   12    2   15   13                                                  
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15   12    9                                                       
CONECT   16    3    1   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21   22                                                  
CONECT   20   18                                                            
CONECT   21   19   23   24                                                  
CONECT   22   19                                                            
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23                                                            
CONECT   26    8                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0000244
HETATM    1  C1  UNL     1       4.578  -2.316   1.269  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.444  -1.474   0.815  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.610  -0.107   0.877  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.581   0.720   0.464  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.798   2.054   0.542  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.837   2.910   0.153  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.019   4.277   0.216  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.088   4.784   0.639  1.00  0.00           O  
HETATM    9  N2  UNL     1       0.999   5.050  -0.197  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.146   4.523  -0.651  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.060   5.322  -1.021  1.00  0.00           O  
HETATM   12  N3  UNL     1      -0.353   3.199  -0.725  1.00  0.00           N  
HETATM   13  C8  UNL     1       0.599   2.319  -0.338  1.00  0.00           C  
HETATM   14  N4  UNL     1       0.386   0.980  -0.415  1.00  0.00           N  
HETATM   15  C9  UNL     1      -0.879   0.532  -0.918  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.912   0.404   0.208  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.561  -0.476   1.185  1.00  0.00           O  
HETATM   18  C11 UNL     1      -3.276   0.249  -0.381  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.315   0.336   0.535  1.00  0.00           O  
HETATM   20  C12 UNL     1      -3.419  -0.969  -1.223  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.659  -0.803  -1.928  1.00  0.00           O  
HETATM   22  C13 UNL     1      -3.542  -2.232  -0.439  1.00  0.00           C  
HETATM   23  O6  UNL     1      -2.460  -2.628   0.285  1.00  0.00           O  
HETATM   24  C14 UNL     1       1.379   0.196  -0.013  1.00  0.00           C  
HETATM   25  C15 UNL     1       1.239  -1.165  -0.065  1.00  0.00           C  
HETATM   26  C16 UNL     1       2.275  -1.982   0.350  1.00  0.00           C  
HETATM   27  C17 UNL     1       2.086  -3.457   0.280  1.00  0.00           C  
HETATM   28  H1  UNL     1       4.597  -3.304   0.766  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.514  -1.801   0.974  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.554  -2.370   2.364  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.542   0.309   1.246  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.125   6.090  -0.154  1.00  0.00           H  
HETATM   33  H6  UNL     1      -1.282   1.339  -1.576  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.826  -0.350  -1.561  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.917   1.458   0.662  1.00  0.00           H  
HETATM   36  H9  UNL     1      -1.893  -0.197   2.067  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.468   1.162  -1.077  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.394   1.230   0.935  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.655  -1.068  -1.995  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.639  -1.442  -2.681  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.743  -3.055  -1.189  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.437  -2.133   0.220  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.706  -3.085   1.111  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.319  -1.569  -0.435  1.00  0.00           H  
HETATM   45  H18 UNL     1       2.673  -3.986   1.054  1.00  0.00           H  
HETATM   46  H19 UNL     1       1.011  -3.660   0.504  1.00  0.00           H  
HETATM   47  H20 UNL     1       2.294  -3.816  -0.738  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3   26
CONECT    3    4   31
CONECT    4    5   24   24
CONECT    5    6    6
CONECT    6    7   13
CONECT    7    8    8    9
CONECT    9   10   32
CONECT   10   11   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   24
CONECT   15   16   33   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   20   37
CONECT   19   38
CONECT   20   21   22   39
CONECT   21   40
CONECT   22   23   41   42
CONECT   23   43
CONECT   24   25
CONECT   25   26   26   44
CONECT   26   27
CONECT   27   45   46   47
END

HMDB0000244
     RDKit          3D
Riboflavin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5779   -2.3163    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.4736    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -0.1066    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.7205    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    2.0538    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    2.9100    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    4.2765    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    4.7839    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    5.0504   -0.1972 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    4.5229   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    5.3224   -1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    3.1986   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    2.3189   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855    0.9800   -0.4146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.5316   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.4044    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5609   -0.4759    1.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.2491   -0.3813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3146    0.3358    0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.9685   -1.2228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6592   -0.8027   -1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -2.2320   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.6276    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    0.1958   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.1649   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -1.9822    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -3.4574    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -3.3040    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -1.8007    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536   -2.3702    2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3092    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    6.0903   -0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3394   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.3501   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173    1.4581    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -0.1967    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675    1.1620   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    1.2301    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -1.0677   -1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.4424   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -3.0549   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -2.1329    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -3.0852    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -1.5688   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730   -3.9864    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -3.6599    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -3.8158   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  2  1  0
 24  4  2  0
 13  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  9 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  6
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
M  END

View in JSmol

Synonyms

Value	Source
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol	ChEBI
5-Deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol	ChEBI
6,7-Dimethyl-9-D-ribitylisoalloxazine	ChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione	ChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine	ChEBI
7,8-Dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4(3H,10H)-dione	ChEBI
7,8-Dimethyl-10-ribitylisoalloxazine	ChEBI
Aqua-flave	ChEBI
Beflavin	ChEBI
Beflavine	ChEBI
Bisulase	ChEBI
Dermadram	ChEBI
e101	ChEBI
Fiboflavin	ChEBI
Flavaxin	ChEBI
Flavin BB	ChEBI
Flaxain	ChEBI
Hyflavin	ChEBI
Lactoflavin	ChEBI
Riboflavin (vit b2)	ChEBI
Riboflavina	ChEBI
Riboflavine	ChEBI
Riboflavinum	ChEBI
Vitamin b2	ChEBI
Vitamin g	ChEBI
Vitasan b2	ChEBI
(-)-Riboflavin	HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol	HMDB
6,7-Dimethyl-9-ribitylisoalloxazine	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione	HMDB
Benzo[g]pteridine riboflavin deriv.	HMDB
e 101	HMDB
FOOD Yellow 15	HMDB
Hyre	HMDB
Lactobene	HMDB
Lactoflavine	HMDB
Ribipca	HMDB
Ribocrisina	HMDB
Riboderm	HMDB
Ribosyn	HMDB
Ribotone	HMDB
Ribovel	HMDB
Russupteridine yellow III	HMDB
San yellow b	HMDB
Vitaflavine	HMDB
Vitamin b 2	HMDB

Chemical Formula

C₁₇H₂₀N₄O₆

Average Mass

376.3639 Da

Monoisotopic Mass

376.13828 Da

IUPAC Name

7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

Traditional Name

riboflavin

CAS Registry Number

83-88-5

SMILES

CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1

InChI Identifier

InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1

InChI Key

AUNGANRZJHBGPY-SCRDCRAPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-30	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-30	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Abramis brama	FooDB	DTU Food
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Agaricus bisporus	FooDB	DTU Food
Agave	FooDB	USDA
Allium ampeloprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa L.	FooDB	DTU Food
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Amelanchier alnifolia	FooDB	Wikipedia
Anacardium occidentale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ananas comosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anarhichas lupus	FooDB	DTU Food
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Angelica keiskei	FooDB	FooDB
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona muricata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona squamosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arabidopsis thaliana	LOTUS Database	35616633
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arctium lappa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Armoracia rusticana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artocarpus altilis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artocarpus heterophyllus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Asparagus officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aspergillus unilateralis	LOTUS Database	35616633
Astacidea	FooDB	DTU Food
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Averrhoa carambola	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Basella alba	FooDB	FooDB
Belone belone	FooDB	DTU Food
Benincasa hispida	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bertholletia excelsa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	DTU Food
Bivalvia	FooDB	USDA
Borago officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bos taurus	FooDB	DTU Food
Bos taurus X Bison bison	FooDB	USDA
Brachyura	FooDB	DTU Food
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	USDA
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gongylodes	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. italica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	DTU Food
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Byrsonima crassifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cajanus cajan	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Canarium ovatum	FooDB	FooDB
Cancer magister	FooDB	USDA
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	DTU Food
Capparis spinosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capra aegagrus hircus	FooDB	USDA
Capsicum annuum	FooDB	All-Creatures
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Caridea	FooDB	DTU Food
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	USDA
Cervidae	FooDB	USDA
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chamerion angustifolium	FooDB	USDA
Chenopodium album	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chenopodium quinoa	FooDB	USDA
Chionoecetes opilio	FooDB	USDA
Chondrus crispus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chrysanthemum coronarium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cicer arietinum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichlidae	FooDB	USDA
Cichorium endivia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum	FooDB	DTU Food
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clinocardium nuttallii	FooDB	USDA
Clupea pallasii	FooDB	USDA
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea canephora	FooDB	DTU Food
Colocasia esculenta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Columbidae	FooDB	DTU Food
Corchorus olitorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coregonus	FooDB	DTU Food
Coregonus nasus	FooDB	USDA
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Corylus	FooDB	DTU Food
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crassostrea gigas	FooDB	USDA
Crassostrea virginica	FooDB	USDA
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita maxima	FooDB	CalorieSlism
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Curcuma longa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	DTU Food
Dallia pectoralis	FooDB	USDA
Daphnia pulex	LOTUS Database	35616633
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dioscorea pentaphylla	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Diospyros	FooDB	DTU Food
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Durio zibethinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	DTU Food
Eleocharis dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Elettaria cardamomum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Empetrum nigrum	FooDB	FooDB
Engraulidae	FooDB	DTU Food
Enteroctopus dofleini	FooDB	USDA
Eragrostis tef	FooDB	USDA
Eremothecium ashbyi	LOTUS Database	35616633
Eremothecium gossypii	LOTUS Database	35616633
Eriobotrya japonica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Formica polyctena	LOTUS Database	35616633
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gallus gallus	FooDB	DTU Food
Garcinia mangostana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gastropoda	FooDB	DTU Food
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	USDA
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus tuberosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hibiscus sabbariffa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	DTU Food
Hippophae rhamnoides	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Hoplostethus atlanticus	FooDB	USDA
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hyssopus officinalis L.	FooDB	FooDB
Ictalurus punctatus	FooDB	USDA
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ipomoea batatas	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans	FooDB	DTU Food
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Katsuwonus pelamis	FooDB	USDA
Lablab purpureus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lactuca sativa	FooDB	DTU Food
Lagenaria siceraria	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lagopus muta	FooDB	DTU Food
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Levisticum officinale	FooDB	FooDB
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Luffa aegyptiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Macadamia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	DTU Food
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mammea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mangifera indica	KNApSAcK Database	22123792
Manihot esculenta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Manilkara zapota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Maranta arundinacea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	DTU Food
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Merlangius merlangus	FooDB	DTU Food
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Micromesistius poutassou	FooDB	DTU Food
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Myoxocephalus	FooDB	USDA
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mytilidae	FooDB	DTU Food
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nephelium lappaceum	FooDB	FooDB
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Nuphar lutea	FooDB	USDA
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Octopus vulgaris	FooDB	DTU Food
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	DTU Food
Oncorhynchus	FooDB	USDA
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus keta	FooDB	USDA
Oncorhynchus kisutch	FooDB	USDA
Oncorhynchus mykiss	FooDB	DTU Food
Oncorhynchus nerka	FooDB	USDA
Oncorhynchus tshawytscha	FooDB	USDA
Ophiodon elongatus	FooDB	USDA
Opuntia	FooDB	DTU Food
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	USDA
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Osmeridae	FooDB	USDA
Ovis aries	FooDB	DTU Food
Pachyrhizus erosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Palinuridae	FooDB	USDA
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Parastichopus californicus	FooDB	USDA
Passiflora edulis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pectinidae	FooDB	USDA
Pediomelum esculentum	FooDB	USDA
Perciformes	FooDB	DTU Food
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petasites japonicus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phasianidae	FooDB	USDA
Phoenix dactylifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Physalis philadelphica var. immaculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phytolacca americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimenta dioica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	DTU Food
Pinus edulis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	DTU Food
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica var. nucipersica	FooDB	DTU Food
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	USDA
Psidium cattleianum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psophocarpus tetragonolobus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Punica granatum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pyrus communis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Ranidae	FooDB	DTU Food
Raphanus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Raphanus sativus var. sativus	FooDB	FooDB
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes rubrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes uva-crispa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	USDA
Rubus idaeus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	USDA
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rumex articus	FooDB	USDA
Saccharina japonica	FooDB	DTU Food
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salmo salar	FooDB	USDA
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sechium edule	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sepiidae	FooDB	USDA
Seriola lalandi	FooDB	USDA
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesbania bispinosa	FooDB	FooDB
Siluriformes	FooDB	DTU Food
Sinapis alba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	DTU Food
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	USDA
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Spirulina	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Squalus acanthias	FooDB	DTU Food
Stenodus leucichthys	FooDB	USDA
Strombidae	FooDB	USDA
Sus scrofa domestica	FooDB	DTU Food
Synechococcus elongatus	LOTUS Database	35616633
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Syzygium cumini	KNApSAcK Database	22123792
Syzygium jambos	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tamarindus indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tetragonia tetragonioides	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thelesperma	FooDB	FooDB
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thunnus	FooDB	DTU Food
Thunnus albacares	FooDB	USDA
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum durum	FooDB	DTU Food
Triticum spelta	FooDB	USDA
Triticum turanicum	FooDB	USDA
Trypanosoma brucei	LOTUS Database	35616633
Tunicata	FooDB	USDA
Typha angustifolia	FooDB	USDA
Vaccinium	FooDB	DTU Food
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium ovalifolium	FooDB	USDA
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	DTU Food
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	USDA
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	USDA
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna aconitifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna angularis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	USDA
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna unguiculata var. sesquipedalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis	FooDB	DTU Food
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Xanthosoma sagittifolium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zizania	FooDB	USDA
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Alloxazines and isoalloxazines

Direct Parent

Flavins

Alternative Parents

Substituents

Flavin
Diazanaphthalene
Quinoxaline
Pyrimidone
Pyrazine
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Polyol
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin (CHEBI:17015 )
Water-soluble vitamins (C00255 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	715.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.085 mg/mL	Not Available
LogP	-1.46	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.92	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.97	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.27 m³·mol⁻¹	ChemAxon
Polarizability	37.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000244

DrugBank ID

DB00140

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Riboflavin

METLIN ID

Not Available

PubChem Compound

493570

PDB ID

Not Available

ChEBI ID

17015

Good Scents ID

rw1136981

References

General References

Mathew JL, Kabi BC, Rath B: Anti-oxidant vitamins and steroid responsive nephrotic syndrome in Indian children. J Paediatr Child Health. 2002 Oct;38(5):450-37. [PubMed:12354259 ]
Booth CK, Clark T, Fenn A: Folic acid, riboflavin, thiamine, and vitamin B-6 status of a group of first-time blood donors. Am J Clin Nutr. 1998 Nov;68(5):1075-80. [PubMed:9808225 ]
Boisvert WA, Mendoza I, Castaneda C, De Portocarrero L, Solomons NW, Gershoff SN, Russell RM: Riboflavin requirement of healthy elderly humans and its relationship to macronutrient composition of the diet. J Nutr. 1993 May;123(5):915-25. [PubMed:8487103 ]
Mikalunas V, Fitzgerald K, Rubin H, McCarthy R, Craig RM: Abnormal vitamin levels in patients receiving home total parenteral nutrition. J Clin Gastroenterol. 2001 Nov-Dec;33(5):393-6. [PubMed:11606856 ]
Belko AZ, Obarzanek E, Roach R, Rotter M, Urban G, Weinberg S, Roe DA: Effects of aerobic exercise and weight loss on riboflavin requirements of moderately obese, marginally deficient young women. Am J Clin Nutr. 1984 Sep;40(3):553-61. [PubMed:6475825 ]
Alexander M, Emanuel G, Golin T, Pinto JT, Rivlin RS: Relation of riboflavin nutriture in healthy elderly to intake of calcium and vitamin supplements: evidence against riboflavin supplementation. Am J Clin Nutr. 1984 Apr;39(4):540-6. [PubMed:6546833 ]
Baeckert PA, Greene HL, Fritz I, Oelberg DG, Adcock EW: Vitamin concentrations in very low birth weight infants given vitamins intravenously in a lipid emulsion: measurement of vitamins A, D, and E and riboflavin. J Pediatr. 1988 Dec;113(6):1057-65. [PubMed:3142982 ]
Maiani G, Mobarhan S, Nicastro A, Virgili F, Scaccini C, Ferro-Luzzi A: [Determination of glutathione reductase activity in erythrocytes and whole blood as an indicator of riboflavin nutrition]. Acta Vitaminol Enzymol. 1983;5(3):171-8. [PubMed:6650303 ]
Bamji MS, Bhaskaram P, Jacob CM: Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles. Ann Nutr Metab. 1987;31(3):191-6. [PubMed:3592624 ]
Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. [PubMed:2631092 ]
Kodentsova VM, Vrzhesinskaya OA, Spirichev VB: Fluorometric riboflavin titration in plasma by riboflavin-binding apoprotein as a method for vitamin B2 status assessment. Ann Nutr Metab. 1995;39(6):355-60. [PubMed:8678471 ]
Bates CJ, Powers HJ: A simple fluorimetric assay for pyridoxamine phosphate oxidase in erythrocyte haemolysates: effects of riboflavin supplementation and of glucose 6-phosphate dehydrogenase deficiency. Hum Nutr Clin Nutr. 1985 Mar;39(2):107-15. [PubMed:4019261 ]
Brun TA, Chen J, Campbell TC, Boreham J, Feng Z, Parpia B, Shen TF, Li M: Urinary riboflavin excretion after a load test in rural China as a measure of possible riboflavin deficiency. Eur J Clin Nutr. 1990 Mar;44(3):195-206. [PubMed:2369885 ]
Mulherin DM, Thurnham DI, Situnayake RD: Glutathione reductase activity, riboflavin status, and disease activity in rheumatoid arthritis. Ann Rheum Dis. 1996 Nov;55(11):837-40. [PubMed:8976642 ]
Rao PN, Levine E, Myers MO, Prakash V, Watson J, Stolier A, Kopicko JJ, Kissinger P, Raj SG, Raj MH: Elevation of serum riboflavin carrier protein in breast cancer. Cancer Epidemiol Biomarkers Prev. 1999 Nov;8(11):985-90. [PubMed:10566553 ]
Zhou X, Huang C, Hong J, Yao S: [Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer]. Wei Sheng Yan Jiu. 2003 Nov;32(6):597-8, 601. [PubMed:14963913 ]
Thurnham DI, Zheng SF, Munoz N, Crespi M, Grassi A, Hambidge KM, Chai TF: Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer. Nutr Cancer. 1985;7(3):131-43. [PubMed:3878498 ]
Bates CJ, Prentice AM, Paul AA, Prentice A, Sutcliffe BA, Whitehead RG: Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement. Trans R Soc Trop Med Hyg. 1982;76(2):253-8. [PubMed:7101408 ]
Dror Y, Stern F, Komarnitsky M: Optimal and stable conditions for the determination of erythrocyte glutathione reductase activation coefficient to evaluate riboflavin status. Int J Vitam Nutr Res. 1994;64(4):257-62. [PubMed:7883462 ]
Switzer BR, Stark AH, Atwood JR, Ritenbaugh C, Travis RG, Wu HM: Development of a urinary riboflavin adherence marker for a wheat bran fiber community intervention trial. Cancer Epidemiol Biomarkers Prev. 1997 Jun;6(6):439-42. [PubMed:9184778 ]
Zempleni J, Galloway JR, McCormick DB: Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans. Am J Clin Nutr. 1996 Jan;63(1):54-66. [PubMed:8604671 ]

Showing NP-Card for Riboflavin (NP0000294)

MOL for NP0000294 (Riboflavin)

3D MOL for NP0000294 (Riboflavin)

3D SDF for NP0000294 (Riboflavin)

3D-SDF for NP0000294 (Riboflavin)

PDB for NP0000294 (Riboflavin)

3D PDB for NP0000294 (Riboflavin)

SMILES for NP0000294 (Riboflavin)

INCHI for NP0000294 (Riboflavin)

Structure for NP0000294 (Riboflavin)

3D Structure for NP0000294 (Riboflavin)