DrugBank: Aetiocholanolone (DB02854)

targets (4)

Identification

Name

Aetiocholanolone

Accession Number

DB02854 (EXPT00443)

Type

small molecule

Groups

experimental

Description

The 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Brand names

Not Available

Brand name mixtures

Not Available

Categories

Not Available

CAS number

53-42-9

Weight

Average: 290.4403
Monoisotopic: 290.224580204

Chemical Formula

C₁₉H₃₀O₂

InChI Key

InChIKey=QGXBDMJGAMFCBF-BNSUEQOYSA-N

InChI

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1

Plain Text

IUPAC Name

(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	6.34e-03 g/l	ALOGPS
logP	3.71	ALOGPS
logP	3.77	ChemAxon Molconvert
logS	-4.66	ALOGPS
pKa	19.96	ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	37.30	ChemAxon Molconvert
rotatable bond count	0	ChemAxon Molconvert
refractivity	83.81	ChemAxon Molconvert
polarizability	34.36	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C04373
PubChem Compound	5880
PubChem Substance	46507911
ChemSpider	5669
ChEBI	28195
ChEMBL	28195
HET	AE2

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1NFQ

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Bile salt sulfotransferase Pharmacological action: unknown Catalyzes the sulfation of steroids and bile acids in the liver and adrenal glands Organism class: human UniProt ID: Q06520 Gene: SULT2A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 2. Dehydrogenase/reductase SDR family member 8 Pharmacological action: unknown Can convert androstan-3-alpha,17-beta-diol (3alpha-diol) to androsterone in vitro, suggesting that it may participate in androgen metabolism during steroidogenesis. May act by metabolizing compounds that stimulate steroid synthesis and/or by generating metabolites that inhibit it. Has no activity toward DHEA (dehydroepiandrosterone), or A-dione (4-androste-3,17-dione), and only a slight activity toward testosterone to A-dione. Tumor- associated antigen in cutaneous T-cell lymphoma Organism class: human UniProt ID: Q8NBQ5 Gene: HSD17B11 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 3. 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase Pharmacological action: unknown Androstan-3-alpha,17-beta-diol + NAD(+) = 17- beta-hydroxyandrostan-3-one + NADH Organism class: bacterial UniProt ID: P69167 Gene: fabG3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 4. Ig gamma-2 chain C region Pharmacological action: unknown Organism class: human UniProt ID: P01859 Gene: IGHG2 Protein Sequence: FASTA SNPs: SNPJam Report References: 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

Targets

1. Bile salt sulfotransferase

Pharmacological action: unknown

Catalyzes the sulfation of steroids and bile acids in the liver and adrenal glands

Organism class: human
UniProt ID: Q06520 Link_out

Gene: SULT2A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

2. Dehydrogenase/reductase SDR family member 8

Pharmacological action: unknown

Can convert androstan-3-alpha,17-beta-diol (3alpha-diol) to androsterone in vitro, suggesting that it may participate in androgen metabolism during steroidogenesis. May act by metabolizing compounds that stimulate steroid synthesis and/or by generating metabolites that inhibit it. Has no activity toward DHEA (dehydroepiandrosterone), or A-dione (4-androste-3,17-dione), and only a slight activity toward testosterone to A-dione. Tumor- associated antigen in cutaneous T-cell lymphoma

Organism class: human
UniProt ID: Q8NBQ5 Link_out

Gene: HSD17B11
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

3. 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase

Pharmacological action: unknown

Androstan-3-alpha,17-beta-diol + NAD(+) = 17- beta-hydroxyandrostan-3-one + NADH

Organism class: bacterial
UniProt ID: P69167 Link_out

Gene: fabG3
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

4. Ig gamma-2 chain C region

Pharmacological action: unknown
Organism class: human
UniProt ID: P01859 Link_out

Gene: IGHG2 Link_out

Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Comments

Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 14:39

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.