NP-MRD: Showing NP-Card for Citrusinol (NP0053311)

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Record Information

Version

2.0

Created at

2022-04-28 00:00:30 UTC

Updated at

2022-04-28 00:00:30 UTC

NP-MRD ID

NP0053311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citrusinol

Description

Citrusinol belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, citrusinol is considered to be a flavonoid lipid molecule. Citrusinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Citrusinol has been detected, but not quantified in, citrus. Citrusinol is found in Bursera leptophloeos, Citrus nobilis , Citrus reticulata and Phyllodium pulchellum . This could make citrusinol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02241209272D          

 26 29  0  0  0  0            999 V2000
   -2.0942   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    1.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -1.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  2  0  0  0  0
  4 26  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 25  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.8912   -0.0045   -1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9458    0.8232   -0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6004    2.1558   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987    1.0881   -1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.7064   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4163   -0.0152    0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -0.2966    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084   -0.9876    2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -1.3776    2.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410   -2.0706    3.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210   -1.1137    2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1418   -1.4824    2.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -2.1088    3.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.1777    1.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -1.5795    2.1751 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.4954    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1783   -0.1159   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.5724   -1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118    0.9850   -2.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1423    0.7033   -2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970    1.1116   -3.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4858    0.0185   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5009   -0.3851   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614   -0.1610    0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1878   -0.4299    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    0.1208    0.6391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9274    0.2475   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069   -1.0842   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7504    0.2917   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3305    2.8810   -1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2390    2.4633    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6886    2.0397   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7677    1.6234   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6288    0.9162   -1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.1998    2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -2.3061    4.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127   -2.0700    3.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    0.8245   -1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.5194   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3401    0.4703   -3.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5328   -0.1925   -0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832   -0.9077    0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 26  1  0
 26  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 24  1  0
 24 25  1  0
 25  6  2  0
  6  5  1  0
  5  4  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  4  2  1  0
 23 17  1  0
  6  7  1  0
 25 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  8 35  1  0
 10 36  1  0
 15 37  1  0
  5 34  1  0
  4 33  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
M  END

  Mrv0541 02241209272D          

 26 29  0  0  0  0            999 V2000
   -2.0942   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    1.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -1.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  2  0  0  0  0
  4 26  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 25  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0053311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O6/c1-20(2)8-7-12-14(26-20)9-13(22)15-16(23)17(24)18(25-19(12)15)10-3-5-11(21)6-4-10/h3-9,21-22,24H,1-2H3

> <INCHI_KEY>
OKQQXHUICMLKQI-UHFFFAOYSA-N

> <FORMULA>
C20H16O6

> <MOLECULAR_WEIGHT>
352.3374

> <EXACT_MASS>
352.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.27937931376662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.664053509333333

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.908543481974354

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.182073578210199

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8210109326513466

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
97.29379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citrusinol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.909  -3.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.577  -2.357   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.577  -0.817   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.909  -0.047   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.909   1.492   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.092   3.803   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.092   2.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.424   1.492   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.759   2.263   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.091  -3.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.426  -2.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.426  -0.817   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.091  -0.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.759  -0.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.759  -2.357   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.761  -3.128   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.761  -2.088   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.244  -2.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.770  -3.803   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.577   3.803   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.577   2.263   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.242   1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.242  -0.047   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.092  -0.817   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.424  -0.047   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.244  -0.817   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4   21                                                       
CONECT    6    7                                                            
CONECT    7    6    8   22                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8                                                            
CONECT   10   11   15                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   10   14                                                       
CONECT   16   11                                                            
CONECT   17   18                                                            
CONECT   18    1   17   19   26                                             
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21    5   20   22                                                  
CONECT   22    7   21   23                                                  
CONECT   23    3   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25    8   14   24                                                  
CONECT   26    4   18                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
3,5-Dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₆O₆

Average Mass

352.3374 Da

Monoisotopic Mass

352.09469 Da

IUPAC Name

3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

Traditional Name

citrusinol

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H16O6/c1-20(2)8-7-12-14(26-20)9-13(22)15-16(23)17(24)18(25-19(12)15)10-3-5-11(21)6-4-10/h3-9,21-22,24H,1-2H3

InChI Key

OKQQXHUICMLKQI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bursera leptophloeos	Plant	KNApSAcK
Citrus nobilis	Plant	KNApSAcK
Citrus reticulata	LOTUS Database	35616633
Phyllodium pulchellum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111994 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.48	ALOGPS
logP	3.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.29 m³·mol⁻¹	ChemAxon
Polarizability	36.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037424

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016472

KNApSAcK ID

C00005077

Chemspider ID

24691934

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44259051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Citrusinol (NP0053311)

MOL for NP0053311 (Citrusinol)

3D MOL for NP0053311 (Citrusinol)

3D SDF for NP0053311 (Citrusinol)

3D-SDF for NP0053311 (Citrusinol)

PDB for NP0053311 (Citrusinol)

3D PDB for NP0053311 (Citrusinol)

SMILES for NP0053311 (Citrusinol)

INCHI for NP0053311 (Citrusinol)

Structure for NP0053311 (Citrusinol)

3D Structure for NP0053311 (Citrusinol)