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Showing NP-Card for 4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan (NP0047816)

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Record Information
Version2.0
Created at2022-03-17 20:46:26 UTC
Updated at2022-03-17 20:46:26 UTC
NP-MRD IDNP0047816
Secondary Accession NumbersNone
Natural Product Identification
Common Name4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan
Description4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan, also known as 2'-O-methylphaseollidinisoflavan, belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, 4',7-dihydroxy-2'-methoxy-3'-prenylisoflavan is considered to be a flavonoid lipid molecule. 4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan has been detected, but not quantified in, cowpea and pulses. 4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan is found in Erythrina x bidwillii. This could make 4',7-dihydroxy-2'-methoxy-3'-prenylisoflavan a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)


  Mrv0541 05061307302D          

 25 27  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  9  8  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16 11  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18  7  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 11  1  0  0  0  0
 20 14  2  0  0  0  0
 21 17  2  0  0  0  0
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 23 19  1  0  0  0  0
 24  3  1  0  0  0  0
 24 21  1  0  0  0  0
 25 12  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
Download

3D MOL for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)

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3D SDF for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)

  Mrv0541 05061307302D          

 25 27  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  9  8  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16 11  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18  7  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 11  1  0  0  0  0
 20 14  2  0  0  0  0
 21 17  2  0  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 19  1  0  0  0  0
 24  3  1  0  0  0  0
 24 21  1  0  0  0  0
 25 12  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CC(O)=C1CC=C(C)C)C1COC2=C(C1)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O4/c1-13(2)4-7-18-19(23)9-8-17(21(18)24-3)15-10-14-5-6-16(22)11-20(14)25-12-15/h4-6,8-9,11,15,22-23H,7,10,12H2,1-3H3

> <INCHI_KEY>
ZEJRFMCOSHZBRD-UHFFFAOYSA-N

> <FORMULA>
C21H24O4

> <MOLECULAR_WEIGHT>
340.4129

> <EXACT_MASS>
340.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.544795609647736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
4.762573610999999

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.971845605957828

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.330999214587475

> <JCHEM_PKA_STRONGEST_BASIC>
-4.552349709316913

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
99.66619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)
Download
PDB for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)
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       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   24                                                            
CONECT    4    7   13                                                       
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7    4   18                                                       
CONECT    8    9   17                                                       
CONECT    9    8   19                                                       
CONECT   10   14   15                                                       
CONECT   11   16   20                                                       
CONECT   12   15   25                                                       
CONECT   13    1    2    4                                                  
CONECT   14    5   10   20                                                  
CONECT   15   10   12   17                                                  
CONECT   16    6   11   22                                                  
CONECT   17    8   15   21                                                  
CONECT   18    7   19   21                                                  
CONECT   19    9   18   23                                                  
CONECT   20   11   14   25                                                  
CONECT   21   17   18   24                                                  
CONECT   22   16                                                            
CONECT   23   19                                                            
CONECT   24    3   21                                                       
CONECT   25   12   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Download
3D PDB for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)
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SMILES for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)
COC1=C(C=CC(O)=C1CC=C(C)C)C1COC2=C(C1)C=CC(O)=C2
Download
INCHI for NP0047816 (4',7-Dihydroxy-2'-methoxy-3'-prenylisoflavan)
InChI=1S/C21H24O4/c1-13(2)4-7-18-19(23)9-8-17(21(18)24-3)15-10-14-5-6-16(22)11-20(14)25-12-15/h4-6,8-9,11,15,22-23H,7,10,12H2,1-3H3
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View in JSmol
Synonyms
ValueSource
2'-O-MethylphaseollidinisoflavanHMDB
Chemical FormulaC21H24O4
Average Mass340.4129 Da
Monoisotopic Mass340.16746 Da
IUPAC Name3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional Name3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-7-ol
CAS Registry Number56257-28-4
SMILES
COC1=C(C=CC(O)=C1CC=C(C)C)C1COC2=C(C1)C=CC(O)=C2
InChI Identifier
InChI=1S/C21H24O4/c1-13(2)4-7-18-19(23)9-8-17(21(18)24-3)15-10-14-5-6-16(22)11-20(14)25-12-15/h4-6,8-9,11,15,22-23H,7,10,12H2,1-3H3
InChI KeyZEJRFMCOSHZBRD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Erythrina x bidwilliiPlant
Vigna unguiculataFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassO-methylated isoflavonoids  
Direct Parent2'-O-methylated isoflavonoids  
Alternative Parents
Substituents
  • 2p-methoxyisoflavonoid-skeleton
    • 

  • Hydroxyisoflavonoid
    • 

  • Isoflavanol
    • 

  • Isoflavan
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • Methoxyphenol
    • 

  • 1-benzopyran
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • 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
logP4.07ALOGPS
logP4.76ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.67 m³·mol⁻¹ChemAxon
Polarizability38.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034010  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012246  
KNApSAcK IDC00009727  
Chemspider ID24843073  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257507  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available