(8alpha,10alpha,13alpha,17beta)-17-[(4-hydroxyphenyl)carbonyl]androsta-3,5-diene-3-carboxylic acid

Identification

Name
(8alpha,10alpha,13alpha,17beta)-17-[(4-hydroxyphenyl)carbonyl]androsta-3,5-diene-3-carboxylic acid
Accession Number
DB08220
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 420.5406
Monoisotopic: 420.230059512
Chemical Formula
C27H32O4
InChI Key
RPNNXCYIESWDSC-JRZBRKEGSA-N
InChI
InChI=1S/C27H32O4/c1-26-13-11-17(25(30)31)15-18(26)5-8-20-21-9-10-23(27(21,2)14-12-22(20)26)24(29)16-3-6-19(28)7-4-16/h3-7,15,20-23,28H,8-14H2,1-2H3,(H,30,31)/t20-,21-,22-,23+,26-,27-/m0/s1
IUPAC Name
(1S,2R,10S,11S,14S,15S)-14-(4-hydroxybenzoyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-5,7-diene-5-carboxylic acid
SMILES
[H][[email protected]@]1(CC[[email protected]@]2([H])[[email protected]]3([H])CC=C4C=C(CC[[email protected]]4(C)[[email protected]@]3([H])CC[[email protected]]12C)C(O)=O)C(=O)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNuclear receptor coactivator 1Not AvailableHuman
UBile acid receptorNot 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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
9845059
PubChem Substance
99444691
ChemSpider
8020773
HET
MUF
PDB Entries
3bej

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 Solubility0.00264 mg/mLALOGPS
logP5.2ALOGPS
logP5.16ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity121.45 m3·mol-1ChemAxon
Polarizability47.84 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.992
Blood Brain Barrier+0.7916
Caco-2 permeable+0.6775
P-glycoprotein substrateSubstrate0.7652
P-glycoprotein inhibitor INon-inhibitor0.9197
P-glycoprotein inhibitor IINon-inhibitor0.8241
Renal organic cation transporterNon-inhibitor0.7864
CYP450 2C9 substrateNon-substrate0.8208
CYP450 2D6 substrateNon-substrate0.914
CYP450 3A4 substrateSubstrate0.7472
CYP450 1A2 substrateInhibitor0.5651
CYP450 2C9 inhibitorNon-inhibitor0.8608
CYP450 2D6 inhibitorNon-inhibitor0.9008
CYP450 2C19 inhibitorNon-inhibitor0.9006
CYP450 3A4 inhibitorNon-inhibitor0.8146
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.779
Ames testNon AMES toxic0.9328
CarcinogenicityNon-carcinogens0.9465
BiodegradationNot ready biodegradable0.9334
Rat acute toxicity2.6597 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9108
hERG inhibition (predictor II)Non-inhibitor0.7738
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 3-carboxy steroids. These are steroid compounds that carry a carboxyl group at the C3-atom of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid acids
Direct Parent
3-carboxy steroids
Alternative Parents
Androstane steroids / Alkyl-phenylketones / Benzoyl derivatives / Aryl alkyl ketones / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
3-carboxy steroid / Androstane-skeleton / Alkyl-phenylketone / Phenylketone / Benzoyl / Aryl alkyl ketone / Aryl ketone / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear re...
Gene Name
NCOA1
Uniprot ID
Q15788
Uniprot Name
Nuclear receptor coactivator 1
Molecular Weight
156755.44 Da
References
  1. 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
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
Molecular Weight
55913.915 Da
References
  1. 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]

Drug created on September 15, 2010 15:29 / Updated on December 01, 2017 16:02