This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Equol
Accession Number
DB11674
Type
Small Molecule
Groups
Investigational
Description

Equol has been used in trials studying the treatment of Breast Cancer.

Structure
Thumb
Synonyms
  • S-equol
Categories
UNII
2T6D2HPX7Q
CAS number
531-95-3
Weight
Average: 242.2699
Monoisotopic: 242.094294314
Chemical Formula
C15H14O3
InChI Key
ADFCQWZHKCXPAJ-GFCCVEGCSA-N
InChI
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
IUPAC Name
(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
SMILES
OC1=CC=C(C=C1)[C@H]1COC2=C(C1)C=CC(O)=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor beta
agonist
Human
USex hormone-binding globulinNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinEquol may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinEquol may decrease the anticoagulant activities of (S)-Warfarin.
3,5-diiodothyropropionic acidThe therapeutic efficacy of 3,5-diiodothyropropionic acid can be decreased when used in combination with Equol.
4-hydroxycoumarinEquol may decrease the anticoagulant activities of 4-hydroxycoumarin.
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Equol.
AbciximabEquol may decrease the anticoagulant activities of Abciximab.
AbituzumabEquol may increase the thrombogenic activities of Abituzumab.
AceclofenacAceclofenac may increase the thrombogenic activities of Equol.
AcenocoumarolEquol may decrease the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidEquol may decrease the anticoagulant activities of Acetylsalicylic acid.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0002209
KEGG Compound
C14131
PubChem Compound
91469
PubChem Substance
347828042
ChemSpider
82594
BindingDB
50410528
ChEBI
34741
ChEMBL
CHEMBL198877
Wikipedia
Equol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentCancer, Breast1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1, 2RecruitingTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentBenign Prostatic Hyperplasia (BPH)1
2CompletedTreatmentMenopause1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0445 mg/mLALOGPS
logP2.91ALOGPS
logP3.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.96 m3·mol-1ChemAxon
Polarizability25.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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
Hydroxyisoflavonoids / 1-benzopyrans / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Oxacyclic compounds / Hydrocarbon derivatives
Substituents
Hydroxyisoflavonoid / Isoflavanol / Chromane / Benzopyran / 1-benzopyran / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Benzenoid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hydroxyisoflavans (CHEBI:34741) / isoflavans, Isoflavanes (C14131)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Mueller SO, Simon S, Chae K, Metzler M, Korach KS: Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. Toxicol Sci. 2004 Jul;80(1):14-25. Epub 2004 Apr 14. [PubMed:15084758]
  2. Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE: S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr. 2005 May;81(5):1072-9. [PubMed:15883431]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Drug created on October 20, 2016 14:38 / Updated on November 02, 2018 07:14