Identification

Name
Equilenin
Accession Number
DB03515  (EXPT01356)
Type
Small Molecule
Groups
Experimental
Description

An estrogenic steroid produced by HORSES. It has a total of five double bonds in the A- and B-ring. High concentration of equilenin is found in the URINE of pregnant mares. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
W8FTJ17C4J
CAS number
Not Available
Weight
Average: 266.3343
Monoisotopic: 266.13067982
Chemical Formula
C18H18O2
InChI Key
PDRGHUMCVRDZLQ-WMZOPIPTSA-N
InChI
InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1
IUPAC Name
(11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),3,5,8-pentaen-14-one
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CCC1=C2C=CC2=C1C=CC(O)=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USteroid Delta-isomeraseNot AvailableComamonas testosteroni
USteroid Delta-isomeraseNot AvailablePseudomonas putida
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)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Equilenin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Equilenin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Equilenin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Equilenin.
5-androstenedioneThe metabolism of Equilenin can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Equilenin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Equilenin.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Equilenin.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Equilenin.
AcalabrutinibThe metabolism of Equilenin can be decreased when combined with Acalabrutinib.
Food Interactions
Not Available

References

Synthesis Reference

Sigfrid Schwarz, "Equilenin derivatives, methods for producing the same and medicaments containing them." U.S. Patent US20040138194, issued July 15, 2004.

US20040138194
General References
Not Available
External Links
KEGG Compound
C14303
PubChem Compound
444865
PubChem Substance
46509080
ChemSpider
392668
BindingDB
50423545
ChEBI
34739
ChEMBL
CHEMBL225546
HET
EQU
Wikipedia
Equilenin
PDB Entries
1cqs / 1gs3 / 1ogx / 1ogz / 1oh0 / 1oho / 1qjg / 1w6y / 3fzw / 3ipt
show 11 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0052 mg/mLALOGPS
logP4.32ALOGPS
logP4.3ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.04 m3·mol-1ChemAxon
Polarizability30.11 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9385
Caco-2 permeable+0.8879
P-glycoprotein substrateSubstrate0.5646
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.8938
Renal organic cation transporterNon-inhibitor0.7572
CYP450 2C9 substrateNon-substrate0.7038
CYP450 2D6 substrateNon-substrate0.8963
CYP450 3A4 substrateSubstrate0.6896
CYP450 1A2 substrateInhibitor0.8458
CYP450 2C9 inhibitorNon-inhibitor0.9438
CYP450 2D6 inhibitorNon-inhibitor0.9583
CYP450 2C19 inhibitorNon-inhibitor0.909
CYP450 3A4 inhibitorNon-inhibitor0.8107
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9085
Ames testNon AMES toxic0.916
CarcinogenicityNon-carcinogens0.8941
BiodegradationNot ready biodegradable0.968
Rat acute toxicity1.7016 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8623
hERG inhibition (predictor II)Inhibitor0.528
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxy delta-7-steroids / 17-oxosteroids / Delta-7-steroids / Phenanthrols / Naphthols and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-hydroxy-delta-7-steroid / 3-hydroxysteroid / Hydroxysteroid / Oxosteroid / 17-oxosteroid / Delta-7-steroid / Phenanthrol / Phenanthrene / 2-naphthol
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
3-hydroxy steroid (CHEBI:34739) / Estrane and derivatives (C14303) / C18 steroids (estrogens) and derivatives (LMST02010007)

Targets

Kind
Protein
Organism
Comamonas testosteroni
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P00947
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
13398.04 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P07445
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
14535.48 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gherezghiher TB, Michalsen B, Chandrasena RE, Qin Z, Sohn J, Thatcher GR, Bolton JL: The naphthol selective estrogen receptor modulator (SERM), LY2066948, is oxidized to an o-quinone analogous to the naphthol equine estrogen, equilenin. Chem Biol Interact. 2012 Mar 5;196(1-2):1-10. doi: 10.1016/j.cbi.2012.01.004. Epub 2012 Jan 28. [PubMed:22290292]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:36