Human Metabolome Database Version 3.5

Showing metabocard for 12a-Hydroxy-3-oxocholadienic acid (HMDB00385)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:26:12 -0600
HMDB ID HMDB00385
Secondary Accession Numbers None
Metabolite Identification
Common Name 12a-Hydroxy-3-oxocholadienic acid
Description 12a-Hydroxy-3-oxocholadienic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 Link_out, 16037564 Link_out, 12576301 Link_out, 11907135 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 12a-Hydroxy-3-oxo-4,6-choladien-24-oate
  2. 12a-Hydroxy-3-oxo-4,6-choladien-24-oic acid
  3. 12a-Hydroxy-3-oxo-Chola-4,6-dienate
  4. 12a-Hydroxy-3-oxo-Chola-4,6-dienic acid
  5. 12a-Hydroxy-3-oxochola-4,6-dienate
  6. 12a-Hydroxy-3-oxochola-4,6-dienic acid
  7. 12a-Hydroxy-3-oxocholadienate
  8. 12a-Hydroxy-3-oxocholadienic acid
Chemical Formula C24H34O4
Average Molecular Weight 386.5244
Monoisotopic Molecular Weight 386.245709576
IUPAC Name (4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl]pentanoic acid
Traditional IUPAC Name (4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl]pentanoic acid
CAS Registry Number 13535-96-1
SMILES C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C
InChI Identifier InChI=1S/C24H34O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h5-6,12,14,17-21,26H,4,7-11,13H2,1-3H3,(H,27,28)/t14-,17?,18?,19?,20?,21+,23+,24-/m1/s1
InChI Key DJVAMCYXFUWMLS-RVOJYKBWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Bile Acids, Alcohols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Bile Acids, Alcohols and Derivatives
  • Monohydroxy Bile Acids, Alcohols and Derivatives
Substituents
  • 12 Hydroxy Steroid
  • 3 Keto Steroid
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Diterpene
  • Ketone
  • Secondary Alcohol
Direct Parent Hydroxy Bile Acids, Alcohols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fat solubilization and Waste products
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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
Water Solubility 0.022 g/L ALOGPS
LogP 3.49 ALOGPS
LogP 3.59 ChemAxon
LogS -4.25 ALOGPS
pKa (strongest acidic) 4.67 ChemAxon
pKa (strongest basic) -0.35 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 110.11 ChemAxon
Polarizability 43.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location
  • Intestine
  • Kidney
  • Liver
  • Gall Bladder
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022003
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00385 Link_out
Metagene Link HMDB00385 Link_out
METLIN ID 5374 Link_out
PubChem Compound 53477691 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Hayakawa, Shohei; Saburi, Yasuo; Fujii, Takao; Sonoda, Yoshiya. Microbiological degradation of bile acids. VII. Partial synthesis of 3,12-dioxo-D4,6-choladienic acid and its derivatives from cholic acid. Journal of Biochemistry (Tokyo, Japan) (1956), 43 731-6.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
  2. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. Pubmed: 10203155 Link_out
  3. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. Pubmed: 11316487 Link_out
  4. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. Pubmed: 16037564 Link_out
  5. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. Pubmed: 12576301 Link_out
  6. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. Pubmed: 11907135 Link_out

Enzymes
Name: Gastrotropin
Reactions: Not Available
Gene Name: FABP6
Uniprot ID: P51161 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Solute carrier organic anion transporter family member 1B3
Reactions: Not Available
Gene Name: SLCO1B3
Uniprot ID: Q9NPD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1B1
Reactions: Not Available
Gene Name: SLCO1B1
Uniprot ID: Q9Y6L6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Canalicular multispecific organic anion transporter 2
Reactions: Not Available
Gene Name: ABCC3
Uniprot ID: O15438 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt export pump
Reactions: Not Available
Gene Name: ABCB11
Uniprot ID: O95342 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ileal sodium/bile acid cotransporter
Reactions: Not Available
Gene Name: SLC10A2
Uniprot ID: Q12908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sodium/bile acid cotransporter
Reactions: Not Available
Gene Name: SLC10A1
Uniprot ID: Q14973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1A2
Reactions: Not Available
Gene Name: SLCO1A2
Uniprot ID: P46721 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 4A1
Reactions: Not Available
Gene Name: SLCO4A1
Uniprot ID: Q96BD0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA