NP-MRD: Showing NP-Card for 7,4'-Dihydroxy-3'-methoxyisoflavan (NP0062314)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 07:00:16 UTC

Updated at

2022-04-28 07:00:16 UTC

NP-MRD ID

NP0062314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,4'-Dihydroxy-3'-methoxyisoflavan

Description

3'-O-Methylequol belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. 7,4'-Dihydroxy-3'-methoxyisoflavan is found in Gliricidia sepium , Glycyrrhiza glabra , Glycyrrhiza inflata and Glycyrrhiza uralensis . 3'-O-Methylequol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.4262    2.1123    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870    0.8061    0.3575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -0.0729    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563    0.2965    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178   -0.5762    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -0.1682    0.2182 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8287   -1.1284    1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2346   -1.1970    1.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.3354    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2748   -0.0021    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    0.8575   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3092    1.1772    0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851    1.3890   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.0689   -1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3634    0.1986   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -0.1879   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594   -1.8320   -0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -2.2418   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678   -1.3399   -0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1848   -1.7522   -0.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200    2.1592    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2889    2.7570    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490    2.5480    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847    1.2962    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089    0.8726    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515   -2.1500    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5258   -0.7796    2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190   -0.4465    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7634    0.8031    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229    2.0698   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674    1.4744   -2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.4243   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9105   -1.2520   -1.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114   -2.5060   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0400   -3.2456   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9177   -1.0971   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 19  3  1  0
 16  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
  6 25  1  1
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
M  END


  Mrv0541 02271201302D          

 20 22  0  0  0  0            999 V2000
    0.9336   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481   -1.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.1355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2191    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    1.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770   -1.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3532    1.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    0.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  7  6  1  6  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-16-7-10(3-5-14(16)18)12-6-11-2-4-13(17)8-15(11)20-9-12/h2-5,7-8,12,17-18H,6,9H2,1H3/t12-/m1/s1

> <INCHI_KEY>
BMADVHDZKAZTNF-GFCCVEGCSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.2958

> <EXACT_MASS>
272.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.08439993512036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.0340066116666664

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.298070019479178

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.626404427026676

> <JCHEM_PKA_STRONGEST_BASIC>
-4.572248850864139

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
75.42340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       1.743  -2.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.076  -2.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.410  -2.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.410  -0.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.076   0.253   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.743  -0.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.409   0.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.409   1.793   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.925   2.563   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.258   1.793   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.592   2.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.926   1.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.926   0.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.592  -0.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.258   0.253   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.925  -0.517   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.744  -2.827   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.259   2.563   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.744   0.253   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.744   1.793   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    8   16    6                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16    7   15                                                       
CONECT   17    3                                                            
CONECT   18   12                                                            
CONECT   19    4   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.2958 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

(3S)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

(3S)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1COC2=CC(O)=CC=C2C1

InChI Identifier

InChI=1S/C16H16O4/c1-19-16-7-10(3-5-14(16)18)12-6-11-2-4-13(17)8-15(11)20-9-12/h2-5,7-8,12,17-18H,6,9H2,1H3/t12-/m1/s1

InChI Key

BMADVHDZKAZTNF-GFCCVEGCSA-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
Gliricidia sepium	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-O-methylated isoflavonoids

Alternative Parents

Substituents

3p-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.97	ALOGPS
logP	3.03	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	29.08 Å³	ChemAxon
Number of Rings	3	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

HMDB0041660

DrugBank ID

Not Available

Phenol Explorer Compound ID

901

FoodDB ID

FDB029818

KNApSAcK ID

Not Available

Chemspider ID

30777592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753179

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 7,4'-Dihydroxy-3'-methoxyisoflavan (NP0062314)

MOL for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

3D MOL for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

3D SDF for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

3D-SDF for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

PDB for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

3D PDB for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

SMILES for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

INCHI for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

Structure for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)

3D Structure for NP0062314 (7,4'-Dihydroxy-3'-methoxyisoflavan)