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Identification
Name(8alpha,10alpha,13alpha,17beta)-17-[(4-hydroxyphenyl)carbonyl]androsta-3,5-diene-3-carboxylic acid
Accession NumberDB08220
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 420.5406
Monoisotopic: 420.230059512
Chemical FormulaC27H32O4
InChI KeyInChIKey=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][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C=C(CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(O)=O)C(=O)C1=CC=C(O)C=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid acids
Direct Parent3-carboxy steroids
Alternative Parents
Substituents
  • 3-carboxy steroid
  • Androstane-skeleton
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 receptors, such as for steroids (PGR, GR and ER), retinoids (RXRs), thyroid hormone (TRs) and prostanoids (PPARs). Also involved in coactivation mediated by STAT3, STAT5A, STAT5B and STAT6 transcription...
Gene Name:
NCOA1
Uniprot ID:
Q15788
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-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt e...
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
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 ]
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Drug created on September 15, 2010 15:29 / Updated on August 17, 2016 12:24