Bovine Metabolome Database: Showing metabocard for Hyodeoxycholic acid (BMDB0000733)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:41 UTC

Update Date

2020-05-11 20:21:27 UTC

BMDB ID

BMDB0000733

Secondary Accession Numbers

BMDB00733

Metabolite Identification

Common Name

Hyodeoxycholic acid

Description

Hyodeoxycholic acid, also known as hyodeoxycholate or 6a-hydroxylithocholate, 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. Hyodeoxycholic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Hyodeoxycholate	Generator
3a,6a-Dihydroxy-5b-cholan-24-Oate	HMDB
3a,6a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
3a,6a-Dihydroxy-5b-cholanate	HMDB
3a,6a-Dihydroxy-5b-cholanic acid	HMDB
3a,6a-Dihydroxy-5b-cholanoate	HMDB
3a,6a-Dihydroxy-5b-cholanoic acid	HMDB
6a-Hydroxylithocholate	HMDB
6a-Hydroxylithocholic acid	HMDB
7-Deoxyhyocholate	HMDB
7-Deoxyhyocholic acid	HMDB
a-Hyodeoxycholate	HMDB
a-Hyodeoxycholic acid	HMDB
alpha-Hyodeoxycholate	HMDB
alpha-Hyodeoxycholic acid	HMDB
Hyodesoxycholate	HMDB
Hyodesoxycholic acid	HMDB
Iodeoxycholate	HMDB
Iodeoxycholic acid	HMDB
3,6-Dihydroxy-5alpha-cholanoic acid	HMDB
NaHDC compound	HMDB
Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomer	HMDB
Hyodeoxycholic acid, (3alpha,6beta)-isomer	HMDB
Hyodeoxycholic acid, sodium salt	HMDB
Murideoxycholic acid	HMDB
Sodium hyodeoxycholate	HMDB
(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
Hyodeoxycholic acid	MeSH

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

83-49-8

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20?,21+,23-,24-/m1/s1

InChI Key

DGABKXLVXPYZII-CDONHWFASA-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
3-hydroxysteroid
3-alpha-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	198.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0598 mg/mL	Not Available
LogP	3.08	RODA,A ET AL. (1990)

Predicted Properties

Property	Value	Source
logP	2.98	ALOGPS
logP	3.71	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-2.7	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	4	ChemAxon
Refractivity	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.69 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	splash10-004m-0329000000-58d5a781e1d72501a6fc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1100290000-3298b2503a68dd31087e	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_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 (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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0009000000-1a7a7cb68338f6eb3692	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-0019000000-7ac011fa76fe71b48725	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-0009000000-77087c5c31c768755c6c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-5910000000-e85c0f620f0f33eda383	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-2900000000-60e4234bfb052d491945	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-2219000000-5b9c1050cbb76dafa745	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-2219000000-be669783febc610d32a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-ba6aa3d13b20ed0d0c09	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0009000000-34256fe4b0144e1f191b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-2219000000-815553fc5ecb67a781b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0009000000-8753654f95e151222293	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-30ddec6babbef6e84fde	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-581fe3701cfd4409cf1c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-9218797d27b939f6059a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02vl-1219000000-acd8de6ea11917fdc1bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0009000000-f969293bf286459bff3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-0009000000-c32f7dbb58c16bc8f793	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-a8bee4058c100d760c3c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054o-0009000000-79e7c3afd290f34646cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3159000000-20e08d1a7b218eb91ebd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9681000000-7db68edc57414ccf438e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-7eba834115ee2c679208	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0009000000-375fefa884fafe6b05bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000g-2009000000-f58a3057b3e321a1006c	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Gallbladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Gallbladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000733

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022211

KNApSAcK ID

Not Available

Chemspider ID

8139282

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hyodeoxycholic acid

METLIN ID

5701

PubChem Compound

9963687

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Eyssen, H. J.; De Pauw, G.; Van Eldere, J. Formation of hyodeoxycholic acid from muricholic acid and hyocholic acid by an unidentified Gram-positive rod termed HDCA-1 isolated from rat intestinal microflora. Applied and Environmental Microbiology (1999),

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Hyodeoxycholic acid (BMDB0000733)

Structure for BMDB0000733 (Hyodeoxycholic acid)