ContaminantDB: 3a,7a-Dihydroxycoprostanic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:14:57 UTC

Update Date

2016-11-09 01:21:11 UTC

Accession Number

CHEM034818

Identification

Common Name

3a,7a-Dihydroxycoprostanic acid

Class

Small Molecule

Description

A cholestanoid that is 5beta-cholestan-26-oic acid substituted by alpha-hydroxy groups at positions 3 and 7 respectively.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3alpha,7alpha-Dihydroxy-5beta-cholestanate	ChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanic acid	ChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanoate	ChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanoic acid	ChEBI
3a,7a-Dihydroxy-5b-cholestanate	Generator
3a,7a-Dihydroxy-5b-cholestanic acid	Generator
3Α,7α-dihydroxy-5β-cholestanate	Generator
3Α,7α-dihydroxy-5β-cholestanic acid	Generator
3a,7a-Dihydroxy-5b-cholestanoate	Generator
3a,7a-Dihydroxy-5b-cholestanoic acid	Generator
3Α,7α-dihydroxy-5β-cholestanoate	Generator
3Α,7α-dihydroxy-5β-cholestanoic acid	Generator
3a,7a-Dihydroxycoprostanate	Generator
3a,7a-Dihydroxycoprostanic acid	Generator
3alpha,7alpha-Dihydroxycoprostanate	Generator
3Α,7α-dihydroxycoprostanate	Generator
3Α,7α-dihydroxycoprostanic acid	Generator
3a,7a-Dihydroxy-5b-cholestan-26-Oate	HMDB
3a,7a-Dihydroxy-5b-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oate	HMDB
3Α,7α-dihydroxy-5β-cholestan-26-Oate	HMDB
3Α,7α-dihydroxy-5β-cholestan-26-Oic acid	HMDB
(3Α,5β,7α)-3,7-dihydroxycholestan-26-Oic acid	HMDB
(3a,5b,7a)-3,7-Dihydroxycholestan-26-Oic acid	HMDB
(3alpha,5beta,7alpha)-3,7-Dihydroxycholestan-26-Oic acid	HMDB
3Α,7α-hydroxy-5β-cholestan-26-Oic acid	HMDB
3a,7a-Hydroxy-5β-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Hydroxy-5β-cholestan-26-Oic acid	HMDB
3a,7a-Hydroxy-5b-cholestan-26-Oate	HMDB
3a,7a-Hydroxy-5b-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Dihydroxycoprostanic acid	HMDB

Chemical Formula

C₂₇H₄₆O₄

Average Molecular Mass

434.652 g/mol

Monoisotopic Mass

434.340 g/mol

CAS Registry Number

17974-66-2

IUPAC Name

(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

Traditional Name

(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

SMILES

[H][C@@]1(CC[C@@]2([H])C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O

InChI Identifier

InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24?,26+,27-/m1/s1

InChI Key

ITZYGDKGRKKBSN-KLYSAGIUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:16577 )
dihydroxy monocarboxylic acid (CHEBI:16577 )
7alpha-hydroxy steroid (CHEBI:16577 )
cholestanoid (CHEBI:16577 )
C27 bile acids, alcohols, and derivatives (LMST04030066 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	4.02	ALOGPS
logP	5.15	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.05 m³·mol⁻¹	ChemAxon
Polarizability	52.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014s-0007900000-55bf6ba08fdb23cc5f37	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-0009200000-3864d6012d9e0f3baf02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06di-1019000000-1d984e3a244a1acc4fd5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0001900000-8b656f3d458df7baa276	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sr-0007900000-8c41fc1f2328cf805012	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-6009200000-226e124be38dd986fd54	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-7d30a0f812b7e3c2a316	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0003900000-0d1d8d80f2d02b013f95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1001900000-5768154ed48ccb53ffa4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ks-1216900000-ef73c5639ce04b841fe1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-2139100000-c7d71db3ab32237bfc53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052k-9670000000-86665221276c4d7674c4	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000359

FooDB ID

FDB021979

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5348

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

4447327

ChEBI ID

16577

PubChem Compound ID

5284239

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Hanson, Russell Floyd. Isolation, identification, formation, and metabolism of 3a, 7a-hydroxy-5b-cholestan-26-oic acid in man. (1972), 73 pp. CAN 78:27152 AN 1973:27152

2. Alme B, Bremmelgaard A, Sjovall J, Thomassen P: Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry. J Lipid Res. 1977 May;18(3):339-62.

3a,7a-Dihydroxycoprostanic acid (CHEM034818)

Structure for CHEM034818: 3a,7a-Dihydroxycoprostanic acid