NP-MRD: Showing NP-Card for (R)-Equol (NP0137156)

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Record Information

Version

2.0

Created at

2022-05-30 16:43:23 UTC

Updated at

2022-05-30 16:43:23 UTC

NP-MRD ID

NP0137156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-Equol

Description

3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Thus, 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol is considered to be a flavonoid lipid molecule. 3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.7856   -0.5479    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4261   -0.4034    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -1.4594    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -1.3312    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.1680   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3099   -0.0175   -0.4705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2729   -1.0731   -1.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.8513   -1.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -0.0924   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.3083   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    1.0506    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7063    1.4513   -0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7453    1.3898    1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    1.0020    1.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.2704    0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.1684    0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.8880   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460    0.7740   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3801   -0.9229   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -2.3970    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -2.1883    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    0.9673   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127   -1.1069   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131   -2.0720   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637    0.0361   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4651    0.8499    0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2429    1.9626    2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819    1.3031    2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.2597    1.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    0.3608    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2078    1.8271   -0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5776    1.6182   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 17  1  0
 17 18  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 18  2  1  0
 16  6  1  0
 10  9  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
 17 31  1  0
 18 32  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 16 29  1  0
 16 30  1  0
 14 28  1  0
 13 27  1  0
 12 26  1  0
 10 25  1  0
M  END


  Mrv1652308221900062D          

 18 20  0  0  0  0            999 V2000
    5.0013   -0.4125    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
    1.4289    0.0000    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
    5.0013    1.2375    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
    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
    4.2868    0.0000    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
    5.7158    0.8250    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
    2.1434   -1.2375    0.0000 C   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
    0.0000   -1.6500    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
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 15 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2

> <INCHI_KEY>
ADFCQWZHKCXPAJ-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.27504316404469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.1916778773333334

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.310681940578428

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.632070985862319

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855539683956429

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
68.96020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
equol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    4   10                                                       
CONECT    2    5   10                                                       
CONECT    3    6   11                                                       
CONECT    4    1   13                                                       
CONECT    5    2   13                                                       
CONECT    6    3   14                                                       
CONECT    7   11   12                                                       
CONECT    8   14   15                                                       
CONECT    9   12   18                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3    7   15                                                  
CONECT   12    7    9   10                                                  
CONECT   13    4    5   16                                                  
CONECT   14    6    8   17                                                  
CONECT   15    8   11   18                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
rac-Equol	ChEMBL, HMDB
(+-)-Isomer OF equol	MeSH, HMDB
3' Hydroxy equol	MeSH, HMDB
3'-Hydroxy-equol	MeSH, HMDB
4'-O-Methyl equol	MeSH, HMDB
4'-Methoxy-7-isoflavanol	MeSH, HMDB
6' Hydroxy equol	MeSH, HMDB
Equol, 4'-O-methyl	MeSH, HMDB
4' O Methyl equol	MeSH, HMDB
4' Methoxy 7 isoflavanol	MeSH, HMDB
6'-Hydroxy-equol	MeSH, HMDB
Equol	MeSH

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

equol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

InChI Identifier

InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2

InChI Key

ADFCQWZHKCXPAJ-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavanol
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080003 )

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	2.91	ALOGPS
logP	3.19	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.96 m³·mol⁻¹	ChemAxon
Polarizability	26.28 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

HMDB0130495

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB089308

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

382975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (R)-Equol (NP0137156)

MOL for NP0137156 ((R)-Equol)

3D MOL for NP0137156 ((R)-Equol)

3D SDF for NP0137156 ((R)-Equol)

3D-SDF for NP0137156 ((R)-Equol)

PDB for NP0137156 ((R)-Equol)

3D PDB for NP0137156 ((R)-Equol)

SMILES for NP0137156 ((R)-Equol)

INCHI for NP0137156 ((R)-Equol)

Structure for NP0137156 ((R)-Equol)

3D Structure for NP0137156 ((R)-Equol)