NP-MRD: Showing NP-Card for Equol (NP0332354)

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Record Information

Version

1.0

Created at

2024-01-10 20:03:03 UTC

Updated at

2024-09-03 04:18:56 UTC

NP-MRD ID

NP0332354

DOI

https://doi.org/10.57994/1568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Equol

Description

Equol, also known as aus-131(S)-equol or 3'-hydroxy-equol, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Equol is an extremely weak basic (essentially neutral) compound (based on its pKa). Equol is a bitter tasting compound. Outside of the human body, Equol is found, on average, in the highest concentration within milk (cow). This could make equol a potential biomarker for the consumption of these foods. It was first documented in 1998 (PMID: 9718497). Equol is a potentially toxic compound (PMID: 12811748) (PMID: 18565930) (PMID: 19679050) (PMID: 17576638).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.1283    1.3382    1.2720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    0.6694    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9863   -0.6650    0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8236   -1.2847    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6316   -0.6173    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315   -1.3622   -0.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1044   -0.8544   -1.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    0.3808   -1.6912 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7301    0.3682   -0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257    1.1736   -1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9766    1.1640   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393    1.9808   -0.7787 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500    0.3253    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856   -0.4816    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -0.4583    0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -1.3351    0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416    0.7258    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    1.3670    0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7566    1.7688    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.2320    0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8928   -2.3454   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7550   -2.4422   -0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256   -1.5805   -2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704   -0.7328   -2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7340    1.8330   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0687    2.9063   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9595    0.2977    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074   -1.1599    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1008   -2.3784    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405   -1.0742    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    1.2958    0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    2.4093    0.9379 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 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
 18  2  1  0
 16  6  1  0
 15  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
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
M  END


  Mrv1652310011709232D          

 18 20  0  0  1  0            999 V2000
   14.5096   -8.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5096   -9.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2239  -10.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9385   -9.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9385   -8.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2239   -8.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6529  -10.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3673   -9.7640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3673   -8.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6529   -8.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0833  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7949   -8.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0833  -11.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978  -11.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -11.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2284  -11.4149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  6  0  0  0
  1 12  1  0  0  0  0
 11 13  2  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
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1

> <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/t12-/m1/s1

> <INCHI_KEY>
ADFCQWZHKCXPAJ-GFCCVEGCSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.2699

> <EXACT_MASS>
242.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.814472608961456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-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                                 01-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-17         0                                  
HETATM    1  C   UNK     0      27.085 -16.686   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.085 -18.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.418 -18.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.752 -18.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.752 -16.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.418 -15.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.085 -18.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.419 -18.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.419 -16.686   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      31.085 -15.916   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      33.756 -18.998   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      25.751 -15.916   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      33.756 -20.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.089 -21.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.423 -20.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.423 -18.998   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.089 -18.228   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      37.760 -21.308   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   13   17                                                  
CONECT   12    1                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
AUS-131(S)-equol	HMDB
(-)-(S)-Equol	HMDB
(-)-Equol	HMDB
(S)-(-)-4',7-Isoflavandiol	HMDB
(S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol	HMDB
(S)-Equol	HMDB
4',7-Dihydroxyisoflavan	HMDB
4',7-Isoflavandiol	HMDB
3'-Hydroxy-equol	HMDB
4' Methoxy 7 isoflavanol	HMDB
4'-O-Methyl equol	HMDB
6'-Hydroxy-equol	HMDB
Equol, 4'-O-methyl	HMDB
3' Hydroxy equol	HMDB
4'-Methoxy-7-isoflavanol	HMDB
6' Hydroxy equol	HMDB
4' O Methyl equol	HMDB
(+-)-Isomer OF equol	HMDB

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2699 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

(3S)-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)[C@H]1COC2=CC(O)=CC=C2C1

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/t12-/m1/s1

InChI Key

ADFCQWZHKCXPAJ-GFCCVEGCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum

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

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

hydroxyisoflavans (CHEBI:34741 )
isoflavans (C14131 )
Isoflavanes (C14131 )

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	25.81 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

HMDB0002209

DrugBank ID

DB11674

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Equol

METLIN ID

Not Available

PubChem Compound

91469

PDB ID

Not Available

ChEBI ID

428126

Good Scents ID

Not Available

References

General References

Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-1264. doi: 10.1002/rcm.1052. [PubMed:12811748 ]
Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]
Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. [PubMed:17576638 ]
King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. doi: 10.1017/s0022029998002891. [PubMed:9718497 ]

Showing NP-Card for Equol (NP0332354)

MOL for NP0332354 (Equol)

3D MOL for NP0332354 (Equol)

3D SDF for NP0332354 (Equol)

3D-SDF for NP0332354 (Equol)

PDB for NP0332354 (Equol)

3D PDB for NP0332354 (Equol)

SMILES for NP0332354 (Equol)

INCHI for NP0332354 (Equol)

Structure for NP0332354 (Equol)

3D Structure for NP0332354 (Equol)