Bovine Metabolome Database: Showing metabocard for 3a,7a-Dihydroxycoprostanic acid (BMDB0000359)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:29:15 UTC

Update Date

2020-05-21 16:28:48 UTC

BMDB ID

BMDB0000359

Secondary Accession Numbers

BMDB00359

Metabolite Identification

Common Name

3a,7a-Dihydroxycoprostanic acid

Description

3alpha,7alpha-Dihydroxycoprostanic acid, also known as 3alpha,7alpha-dihydroxy-5beta-cholestanate or 3α,7α-dihydroxy-5β-cholestanate, 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. 3alpha,7alpha-Dihydroxycoprostanic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

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 Weight

434.661

Monoisotopic Molecular Weight

434.339609961

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

CAS Registry Number

17974-66-2

SMILES

[H][C@@]1(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])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-HKFUITGCSA-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 )

Ontology

Status

Expected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
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_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_3_1) - 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_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014s-0007900000-55bf6ba08fdb23cc5f37	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-0009200000-3864d6012d9e0f3baf02	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06di-1019000000-1d984e3a244a1acc4fd5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0001900000-8b656f3d458df7baa276	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sr-0007900000-8c41fc1f2328cf805012	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-6009200000-226e124be38dd986fd54	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-7d30a0f812b7e3c2a316	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0003900000-0d1d8d80f2d02b013f95	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1001900000-5768154ed48ccb53ffa4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ks-1216900000-ef73c5639ce04b841fe1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-2139100000-c7d71db3ab32237bfc53	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052k-9670000000-86665221276c4d7674c4	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Bile Acid Biosynthesis		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000359

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021979

KNApSAcK ID

Not Available

Chemspider ID

4447327

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5348

PubChem Compound

5284239

PDB ID

Not Available

ChEBI ID

16577

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:: CYP11A1
Uniprot ID:: P00189
Molecular weight:: 60333.0

Reactions

3a,7a-Dihydroxy-5b-cholestan-26-al → 3a,7a-Dihydroxycoprostanic acid	details

Enzyme Details

2. Long-chain fatty acid transport protein 1

General function:: Not Available
Specific function:: Mediates the ATP-dependent import of long-chain fatty acids (LCFA) into the cell by mediating their translocation at the plasma membrane. Has also an acyl-CoA ligase activity for long-chain and very-long-chain fatty acids. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane-associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LCFA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism.
Gene Name:: SLC27A1
Uniprot ID:: Q3ZKN0
Molecular weight:: 71123.0

Reactions

3a,7a-Dihydroxycoprostanic acid + Adenosine triphosphate + Coenzyme A → 3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Pyrophosphate + 3'-AMP	details

Showing metabocard for 3a,7a-Dihydroxycoprostanic acid (BMDB0000359)

Structure for BMDB0000359 (3a,7a-Dihydroxycoprostanic acid)

Enzymes

Reactions

Reactions