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Record Information

Version

2.0

Creation Date

2012-10-10 12:20:08 -0600

Update Date

2015-09-16 14:50:11 -0600

Secondary Accession Numbers

ECMDB23167

Identification

Name:

3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate

Description

3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate is a steroid derivative or bile acid. It is a substrate for the enzyme 7-alpha-hydroxysteroid dehydrogenase, which catalyzes the following reaction: 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate + NAD+ = 3-alpha,12-alpha-dihydroxy-7-oxo-5-beta-cholanate + NADH.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid
(3a,5b,7a,8a,12a,14b,17a)-3,7,12-Trihydroxycholan-24-Oate
(3a,5b,7a,8a,12a,14b,17a)-3,7,12-Trihydroxycholan-24-Oic acid
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate
(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid
(3alpha,5beta,7alpha,8alpha,12alpha,14beta,17alpha)-3,7,12-Trihydroxycholan-24-Oate
(3alpha,5beta,7alpha,8alpha,12alpha,14beta,17alpha)-3,7,12-trihydroxycholan-24-oic acid
(3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-Oate
(3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-Oic acid
(3α,5β,7α,8α,12α,14β,17α)-3,7,12-Trihydroxycholan-24-Oate
(3α,5β,7α,8α,12α,14β,17α)-3,7,12-Trihydroxycholan-24-Oic acid
(4R)-4-(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopentaaphenanthren-17-ylpentanoate
(4R)-4-(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopentaaphenanthren-17-ylpentanoic acid
3-a,7-a,12-a-Trihydroxy-5-b-cholanate
3-a,7-a,12-a-Trihydroxy-5-b-cholanic acid
3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholanic acid
3-α,7-α,12-α-Trihydroxy-5-β-cholanate
3-α,7-α,12-α-Trihydroxy-5-β-cholanic acid
3a,7a,12a-Trihydroxy-5b-cholanate
3a,7a,12a-Trihydroxy-5b-cholanic acid
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid
3α,7α,12α-Trihydroxy-5β-cholanate
3α,7α,12α-Trihydroxy-5β-cholanic acid
Cholate
Cholic acid
Cholsaeure

Chemical Formula:

C₂₄H₄₀O₅

Weight:

Average: 408.5714
Monoisotopic: 408.28757439

InChI Key:

BHQCQFFYRZLCQQ-OELDTZBJSA-N

InChI:

InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

CAS number:

Not Available

IUPAC Name:

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional IUPAC Name:

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:16359 )
trihydroxy-5beta-cholanic acid (CHEBI:16359 )
C24 bile acids, alcohols, and derivatives (C00695 )
Cholane and derivatives (C00695 )
C24 bile acids, alcohols, and derivatives (LMST04010001 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
logP	2.48	ChemAxon
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.79 m³·mol⁻¹	ChemAxon
Polarizability	47.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate + NAD > 3-alpha,12-alpha-dihydroxy-7-oxo-5-beta-cholanate + NADH

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fk9-5796000000-2876080f3fa17fb96370	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fk9-5796000000-2876080f3fa17fb96370	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-0439000000-4e43231560df6c61b96d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1100049000-86faaffe1dc0eadf9e75	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0000900000-806d3b03c76019afbf7d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0000900000-4edb603ca5534669120e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0000900000-4a76e64b2f0411d0b701	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0001900000-41aa3a7cb25fcf549046	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0057900000-790a3808fa512d5d1687	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0010900000-e6bedfc253363160a37e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0030900000-da4a7bfccbaf1e42171c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0020900000-772055897702843a1d50	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0021900000-0405fe63d70d3a88bf6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0aou-3844900000-cb3c2aba1b9a29785616	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0007-0019000000-fb9a5b5952cf65eb7988	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0001900000-9583bd9c6c0d2b069b68	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-1027900000-31f3cf065ad48561c0a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-b0504ee652d51a711f3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-18dd8b6be45775ec83c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-285d3d0d87f5471b419a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-0fcb0f6819b05ab63c12	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-b0504ee652d51a711f3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-18dd8b6be45775ec83c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-285d3d0d87f5471b419a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-0fcb0f6819b05ab63c12	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-6fe7340aea27993f6ecb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-0001900000-9e5ac05d22599c16d77a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-a58dbdca74695c9c40e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-1c1c35b35f948ca53943	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0596-9642000000-e425981b8a0ac72ea6ee	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16359
HMDB ID	HMDB0000619
Pubchem Compound ID	221493
Kegg ID	C00695
ChemSpider ID	192176
Wikipedia ID	Cholic_Acid
BioCyc ID	Not Available
Ligand Expo	CHD

Enzymes

Protein Details

1. 7-alpha-hydroxysteroid dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: 7-alpha-dehydroxylation of cholic acid, yielding deoxycholic acid and lithocholic acid, respectively. Highest affinity with taurochenodeoxycholic acid
Gene Name:: hdhA
Uniprot ID:: P0AET8
Molecular weight:: 26778

Reactions

3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate + NAD(+) = 3-alpha,12-alpha-dihydroxy-7-oxo-5-beta-cholanate + NADH.

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate (M2MDB003557)

Structure for #<Compound:0xa95263a0>

Enzymes

Reactions