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Showing NP-Card for Sojagol (NP0047823)

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Record Information
Version2.0
Created at2022-03-17 20:46:33 UTC
Updated at2022-03-17 20:46:33 UTC
NP-MRD IDNP0047823
Secondary Accession NumbersNone
Natural Product Identification
Common NameSojagol
DescriptionSojagol, also known as soyagol, belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, sojagol is considered to be a flavonoid lipid molecule. Sojagol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Sojagol has been detected, but not quantified in, pulses and soy beans. Sojagol is found in Phaseolus aureus . Sojagol was first documented in 1975 (PMID: 16659156). This could make sojagol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047823 (Sojagol)


  Mrv0541 05061307302D          

 25 29  0  0  0  0            999 V2000
    5.8777   -0.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982   -1.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459   -2.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529   -2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107   -0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -0.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -0.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -1.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3078   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689   -1.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168   -2.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -0.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -3.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099   -2.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -0.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148   -1.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 11  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 21 10  1  0  0  0  0
 22 19  2  0  0  0  0
 23 15  1  0  0  0  0
 23 19  1  0  0  0  0
 24 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
Download

3D MOL for NP0047823 (Sojagol)

Download
3D SDF for NP0047823 (Sojagol)

  Mrv0541 05061307302D          

 25 29  0  0  0  0            999 V2000
    5.8777   -0.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982   -1.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459   -2.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529   -2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107   -0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -0.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -0.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -1.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3078   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689   -1.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168   -2.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -0.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -3.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099   -2.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -0.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148   -1.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 11  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 21 10  1  0  0  0  0
 22 19  2  0  0  0  0
 23 15  1  0  0  0  0
 23 19  1  0  0  0  0
 24 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2=C(O1)C=CC1=C2OC2=C1C(=O)OC1=C2C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-20(2)8-7-12-14(25-20)6-5-13-16-18(24-17(12)13)11-4-3-10(21)9-15(11)23-19(16)22/h3-6,9,21H,7-8H2,1-2H3

> <INCHI_KEY>
GSAVLDZAGYKJSO-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.951293439874036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),2(11),5(10),6,8,14(19),20-heptaen-3-one

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
3.724824242666666

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1439871949647245

> <JCHEM_PKA_STRONGEST_BASIC>
-4.25300019636183

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
91.0694

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sojagol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047823 (Sojagol)
Download
PDB for NP0047823 (Sojagol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.972  -0.006   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.383  -1.943   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.476  -0.075   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.030  -0.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.059  -4.789   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.565  -4.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.487  -0.396   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.993  -0.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.030  -2.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.506  -1.220   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.506  -1.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.011  -1.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.029  -3.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.041  -3.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.476  -3.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.489  -3.645   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.504  -2.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.013  -2.180   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.458  -4.789   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.023  -1.220   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.013  -0.900   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.934  -6.254   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.952  -4.469   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.259  -1.275   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.548  -2.684   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7    8   12                                                       
CONECT    8    7   20                                                       
CONECT    9   10   15                                                       
CONECT   10    3    9   21                                                  
CONECT   11    4   15   18                                                  
CONECT   12    7   14   17                                                  
CONECT   13    5   16   17                                                  
CONECT   14    6   12   25                                                  
CONECT   15    9   11   23                                                  
CONECT   16   13   18   19                                                  
CONECT   17   12   13   24                                                  
CONECT   18   11   16   24                                                  
CONECT   19   16   22   23                                                  
CONECT   20    1    2    8   25                                             
CONECT   21   10                                                            
CONECT   22   19                                                            
CONECT   23   15   19                                                       
CONECT   24   17   18                                                       
CONECT   25   14   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

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3D PDB for NP0047823 (Sojagol)
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SMILES for NP0047823 (Sojagol)
CC1(C)CCC2=C(O1)C=CC1=C2OC2=C1C(=O)OC1=C2C=CC(O)=C1
Download
INCHI for NP0047823 (Sojagol)
InChI=1S/C20H16O5/c1-20(2)8-7-12-14(25-20)6-5-13-16-18(24-17(12)13)11-4-3-10(21)9-15(11)23-19(16)22/h3-6,9,21H,7-8H2,1-2H3
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Synonyms
ValueSource
2,3-Dihydro-10-hydroxy-3,3-dimethyl-1H,7H-furo[2,3-c:5,4-f']bis[1]benzopyran-7-one, 9ciHMDB
SoyagolHMDB
Chemical FormulaC20H16O5
Average Mass336.3380 Da
Monoisotopic Mass336.09977 Da
IUPAC Name7-hydroxy-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),2(11),5(10),6,8,14(19),20-heptaen-3-one
Traditional Namesojagol
CAS Registry Number18979-00-5
SMILES
CC1(C)CCC2=C(O1)C=CC1=C2OC2=C1C(=O)OC1=C2C=CC(O)=C1
InChI Identifier
InChI=1S/C20H16O5/c1-20(2)8-7-12-14(25-20)6-5-13-16-18(24-17(12)13)11-4-3-10(21)9-15(11)23-19(16)22/h3-6,9,21H,7-8H2,1-2H3
InChI KeyGSAVLDZAGYKJSO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycine maxFooDB
Phaseolus aureusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassCoumestans  
Direct ParentCoumestans  
Alternative Parents
Substituents
  • Coumestan
    • 

  • Angular furanocoumarin
    • 

  • Furanocoumarin
    • 

  • 2,2-dimethyl-1-benzopyran
    • 

  • Coumarin
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzofuran
    • 

  • Furopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Furan
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen 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
logP4.36ALOGPS
logP3.72ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)7.14ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.07 m³·mol⁻¹ChemAxon
Polarizability35.95 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034027  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012265  
KNApSAcK IDC00002572  
Chemspider ID4445120  
KEGG Compound IDC10529  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281809  
PDB IDNot Available
ChEBI ID9183  
Good Scents IDNot Available
References
General References
  1. Keen NT, Taylor OC: Ozone injury in soybeans: isoflavonoid accumulation is related to necrosis. Plant Physiol. 1975 Apr;55(4):731-3. doi: 10.1104/pp.55.4.731. [PubMed:16659156  ]