Np mrd loader

Showing NP-Card for Eriocitrin (NP0050107)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 21:23:23 UTC
Updated at2022-03-17 21:23:23 UTC
NP-MRD IDNP0050107
Secondary Accession NumbersNone
Natural Product Identification
Common NameEriocitrin
DescriptionEriocitrin, also known as eriodictioside, belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Eriocitrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Eriocitrin is found in Citrus latipes, Citrus maxima, Citrus paradisi, Citrus sinensis, Citrus spp., Citrus sudachi , Citrus unshiu, Citrus wilsonii, Cyclopia subternata, Lycopus europaeus, Mentha piperita, Mentha piperita , Myoporum tenuifolium and Satureja montana. Eriocitrin was first documented in 1998 (PMID: 9688172). A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage (PMID: 12551749) (PMID: 15315375) (PMID: 17690486).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050107 (Eriocitrin)


  Mrv1652301212022263D          

 42 46  0  0  0  0            999 V2000
    7.2522    1.3814   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0549    0.5697    1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1989    0.6347    2.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9209   -1.2136   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7588   -0.3147   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1693    0.3320    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5359   -1.6981   -1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2416   -0.5645    1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2995   -0.0907   -0.7346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8836   -0.3433    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9167    0.3567   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2255   -0.2402    1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0898   -1.1671    0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -0.9734   -2.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2264   -1.6582   -2.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6656   -0.4130   -0.5655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2512   -0.3095   -0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061    0.3469    0.2675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0780   -0.9770   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3802   -0.7826    0.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1312    1.5982   -0.1744 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7426   -1.8017    1.0227 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2499    2.8202    0.0234 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6137   -1.1806    1.7891 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8197    2.6160   -0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6212   -0.5848    0.7736 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4080    1.2063   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.4100   -0.2071    2.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1525   -2.0417    0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -1.6665   -3.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -2.2207   -3.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1859   -1.4928   -0.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377    1.4999   -1.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7614   -2.2540    1.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    3.3709    1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1085   -0.2336    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959    2.9026   -1.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -1.0740    0.9200 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1349   -0.7798   -0.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152    1.0298    0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5107   -0.3365    0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401    0.6094    0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  2  0  0  0  0
  4 13  1  0  0  0  0
  5 11  2  0  0  0  0
  5 14  1  0  0  0  0
  6 11  1  0  0  0  0
  6 17  2  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
 18  8  1  1  0  0  0
  8 38  1  0  0  0  0
  9 20  1  0  0  0  0
  9 39  1  0  0  0  0
 10 16  1  0  0  0  0
 11 40  1  0  0  0  0
 12 13  2  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 14 19  2  0  0  0  0
 14 30  1  0  0  0  0
 15 19  1  0  0  0  0
 15 31  2  0  0  0  0
 16 41  1  0  0  0  0
 17 19  1  0  0  0  0
 17 41  1  0  0  0  0
 18 21  1  0  0  0  0
 18 42  1  0  0  0  0
 20 22  1  0  0  0  0
 20 32  1  6  0  0  0
 21 23  1  0  0  0  0
 21 33  1  6  0  0  0
 22 24  1  0  0  0  0
 22 34  1  1  0  0  0
 23 25  1  0  0  0  0
 23 35  1  1  0  0  0
 24 26  1  0  0  0  0
 24 36  1  1  0  0  0
 25 27  1  0  0  0  0
 25 37  1  6  0  0  0
 26 38  1  6  0  0  0
 26 39  1  0  0  0  0
 27 40  1  1  0  0  0
 27 42  1  0  0  0  0
M  END
Download

3D MOL for NP0050107 (Eriocitrin)

Download
3D SDF for NP0050107 (Eriocitrin)

  Mrv1652301212022263D          

 42 46  0  0  0  0            999 V2000
    7.2522    1.3814   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0549    0.5697    1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1989    0.6347    2.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9209   -1.2136   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7588   -0.3147   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1693    0.3320    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5359   -1.6981   -1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2416   -0.5645    1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2995   -0.0907   -0.7346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8836   -0.3433    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9167    0.3567   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2255   -0.2402    1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0898   -1.1671    0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -0.9734   -2.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2264   -1.6582   -2.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6656   -0.4130   -0.5655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2512   -0.3095   -0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061    0.3469    0.2675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0780   -0.9770   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3802   -0.7826    0.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1312    1.5982   -0.1744 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7426   -1.8017    1.0227 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2499    2.8202    0.0234 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6137   -1.1806    1.7891 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8197    2.6160   -0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6212   -0.5848    0.7736 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4080    1.2063   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.4100   -0.2071    2.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1525   -2.0417    0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -1.6665   -3.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -2.2207   -3.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1859   -1.4928   -0.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377    1.4999   -1.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7614   -2.2540    1.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    3.3709    1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1085   -0.2336    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959    2.9026   -1.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -1.0740    0.9200 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1349   -0.7798   -0.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152    1.0298    0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5107   -0.3365    0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401    0.6094    0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  2  0  0  0  0
  4 13  1  0  0  0  0
  5 11  2  0  0  0  0
  5 14  1  0  0  0  0
  6 11  1  0  0  0  0
  6 17  2  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
 18  8  1  1  0  0  0
  8 38  1  0  0  0  0
  9 20  1  0  0  0  0
  9 39  1  0  0  0  0
 10 16  1  0  0  0  0
 11 40  1  0  0  0  0
 12 13  2  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 14 19  2  0  0  0  0
 14 30  1  0  0  0  0
 15 19  1  0  0  0  0
 15 31  2  0  0  0  0
 16 41  1  0  0  0  0
 17 19  1  0  0  0  0
 17 41  1  0  0  0  0
 18 21  1  0  0  0  0
 18 42  1  0  0  0  0
 20 22  1  0  0  0  0
 20 32  1  6  0  0  0
 21 23  1  0  0  0  0
 21 33  1  6  0  0  0
 22 24  1  0  0  0  0
 22 34  1  1  0  0  0
 23 25  1  0  0  0  0
 23 35  1  1  0  0  0
 24 26  1  0  0  0  0
 24 36  1  1  0  0  0
 25 27  1  0  0  0  0
 25 37  1  6  0  0  0
 26 38  1  6  0  0  0
 26 39  1  0  0  0  0
 27 40  1  1  0  0  0
 27 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C[C@H](OC4=C3)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

> <INCHI_KEY>
OMQADRGFMLGFJF-MNPJBKLOSA-N

> <FORMULA>
C27H32O15

> <MOLECULAR_WEIGHT>
596.534

> <EXACT_MASS>
596.174120354

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.48627262051773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-0.46045104366666645

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.31429071955271

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.536076051024976

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648685994297116

> <JCHEM_POLAR_SURFACE_AREA>
245.2899999999999

> <JCHEM_REFRACTIVITY>
136.28469999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eriocitrin

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050107 (Eriocitrin)
Download
PDB for NP0050107 (Eriocitrin)
HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0       7.252   1.381  -0.461  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.055   0.570   1.256  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.199   0.635   2.015  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.921  -1.214  -0.002  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.759  -0.315  -1.537  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.169   0.332   0.237  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.536  -1.698  -1.349  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.242  -0.565   1.190  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.300  -0.091  -0.735  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.884  -0.343   0.240  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.917   0.357  -0.343  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.226  -0.240   1.764  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.090  -1.167   0.754  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.837  -0.973  -2.098  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.226  -1.658  -2.061  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.666  -0.413  -0.566  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.251  -0.310  -0.294  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.506   0.347   0.268  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.078  -0.977  -1.489  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.380  -0.783   0.084  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.131   1.598  -0.174  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.743  -1.802   1.023  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.250   2.820   0.023  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.614  -1.181   1.789  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.820   2.616  -0.304  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.621  -0.585   0.774  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.408   1.206  -0.077  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.410  -0.207   2.516  0.00  0.00           O+0
HETATM   29  O   UNK     0     -11.152  -2.042   0.523  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.728  -1.667  -3.305  0.00  0.00           O+0
HETATM   31  O   UNK     0      -5.093  -2.221  -3.183  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.186  -1.493  -0.801  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.538   1.500  -1.519  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.761  -2.254   1.852  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.450   3.371   1.289  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.109  -0.234   2.666  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.596   2.903  -1.665  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.408  -1.074   0.920  0.00  0.00           O+0
HETATM   39  O   UNK     0       6.135  -0.780  -0.540  0.00  0.00           O+0
HETATM   40  O   UNK     0      -0.915   1.030   0.279  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.511  -0.337   0.286  0.00  0.00           O+0
HETATM   42  O   UNK     0       1.240   0.609   0.866  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3   10                                                       
CONECT    3    2   12                                                       
CONECT    4   10   13                                                       
CONECT    5   11   14                                                       
CONECT    6   11   17                                                       
CONECT    7   15   16                                                       
CONECT    8   18   38                                                       
CONECT    9    1   20   39                                                  
CONECT   10    2    4   16                                                  
CONECT   11    5    6   40                                                  
CONECT   12    3   13   28                                                  
CONECT   13    4   12   29                                                  
CONECT   14    5   19   30                                                  
CONECT   15    7   19   31                                                  
CONECT   16    7   10   41                                                  
CONECT   17    6   19   41                                                  
CONECT   18    8   21   42                                                  
CONECT   19   14   15   17                                                  
CONECT   20    9   22   32                                                  
CONECT   21   18   23   33                                                  
CONECT   22   20   24   34                                                  
CONECT   23   21   25   35                                                  
CONECT   24   22   26   36                                                  
CONECT   25   23   27   37                                                  
CONECT   26   24   38   39                                                  
CONECT   27   25   40   42                                                  
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   15                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
CONECT   37   25                                                            
CONECT   38    8   26                                                       
CONECT   39    9   26                                                       
CONECT   40   11   27                                                       
CONECT   41   16   17                                                       
CONECT   42   18   27                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

Download
3D PDB for NP0050107 (Eriocitrin)
Download
SMILES for NP0050107 (Eriocitrin)
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C[C@H](OC4=C3)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Download
INCHI for NP0050107 (Eriocitrin)
InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
Download
View in JSmol
Synonyms
ValueSource
EriodictiosideChEBI
Eriodictyol 7-O-rutinosideChEBI
Eriodictyol 7-O-beta-rutinosideMeSH
Chemical FormulaC27H32O15
Average Mass596.5340 Da
Monoisotopic Mass596.17412 Da
IUPAC Name(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Nameeriocitrin
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C[C@H](OC4=C3)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
InChI KeyOMQADRGFMLGFJF-MNPJBKLOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus aurantiifoliaFooDB
Citrus latipesLOTUS Database
Citrus limonFooDB
Citrus maximaLOTUS Database
Citrus paradisiLOTUS Database
Citrus sinensisLOTUS Database
Citrus spp.Plant
Citrus sudachiPlant
Citrus unshiuLOTUS Database
Citrus wilsoniiLOTUS Database
Cyclopia subternataLOTUS Database
Lycopus europaeusLOTUS Database
Mentha piperitaLOTUS Database
Mentha x piperitaPlant
Myoporum tenuifoliumPlant
Satureja montanaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid-7-O-glycosides  
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • Flavanone
    • 

  • Hydroxyflavonoid
    • 

  • Flavan
    • 

  • Phenolic glycoside
    • 

  • Chromone
    • 

  • Disaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Catechol
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Acetal
    • 

  • Polyol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.35ALOGPS
logP-0.46ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.54ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity136.28 m³·mol⁻¹ChemAxon
Polarizability57.49 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00008295  
Chemspider IDNot Available
KEGG Compound IDC09732  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEriocitrin  
METLIN IDNot Available
PubChem Compound83489  
PDB IDNot Available
ChEBI ID28709  
Good Scents IDNot Available
References
General References
  1. Minato K, Miyake Y, Fukumoto S, Yamamoto K, Kato Y, Shimomura Y, Osawa T: Lemon flavonoid, eriocitrin, suppresses exercise-induced oxidative damage in rat liver. Life Sci. 2003 Feb 21;72(14):1609-16. doi: 10.1016/s0024-3205(02)02443-8. [PubMed:12551749  ] 
  2. Kamara BI, Brand DJ, Brandt EV, Joubert E: Phenolic metabolites from honeybush tea (Cyclopia subternata). J Agric Food Chem. 2004 Aug 25;52(17):5391-5. doi: 10.1021/jf040097z. [PubMed:15315375  ] 
  3. Miyake Y, Mochizuki M, Okada M, Hiramitsu M, Morimitsu Y, Osawa T: Isolation of antioxidative phenolic glucosides from lemon juice and their suppressive effect on the expression of blood adhesion molecules. Biosci Biotechnol Biochem. 2007 Aug;71(8):1911-9. doi: 10.1271/bbb.70115. Epub 2007 Aug 7. [PubMed:17690486  ] 
  4. Miyake Y, Yamamoto K, Tsujihara N, Osawa T: Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids. 1998 Jul;33(7):689-95. doi: 10.1007/s11745-998-0258-y. [PubMed:9688172  ]