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Human Metabolome Database Version 3.5

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Showing metabocard for 12-Ketodeoxycholic acid (HMDB00328)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:19 -0700
HMDB ID HMDB00328
Secondary Accession Numbers None
Metabolite Identification
Common Name 12-Ketodeoxycholic acid
Description 12-Ketodeoxycholic 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 | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3a,5b)-3-hydroxy-12-oxo-cholan-24-oate
  2. (3a,5b)-3-hydroxy-12-oxo-cholan-24-oic acid
  3. (3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oate
  4. (3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oic acid
  5. 12-Dehydrodeoxycholate
  6. 12-Dehydrodeoxycholic acid
  7. 12-Ketodeoxycholate
  8. 12-Ketodeoxycholic acid
  9. 12-Ketolithocholate
  10. 12-Ketolithocholic acid
  11. 12-Oxo-3a-hydroxy-5b-cholanate
  12. 12-Oxo-3a-hydroxy-5b-cholanic acid
  13. 12-Oxolithocholate
  14. 12-Oxolithocholic acid
  15. 3a-Hydroxy-12-oxo-5b-cholan-24-oate
  16. 3a-Hydroxy-12-oxo-5b-cholan-24-oic acid
  17. 3a-Hydroxy-12-oxo-5b-cholanate
  18. 3a-Hydroxy-12-oxo-5b-cholanic acid
  19. 3a-Hydroxy-12-oxo-5b-cholanoate
  20. 3a-Hydroxy-12-oxo-5b-cholanoic acid
Chemical Formula C24H38O4
Average Molecular Weight 390.5561
Monoisotopic Molecular Weight 390.277009704
IUPAC Name (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number 5130-29-0
SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1
InChI Key CVNYHSDFZXHMMJ-VPUMZWJWSA-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
  • C24 bile acids, alcohols, and derivatives(Lipidmaps)
  • Monohydroxy Bile Acids, Alcohols and Derivatives
Substituents
  • 12 Keto Steroid
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • 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 0.013 g/L ALOGPS
LogP 3.78 ALOGPS
LogP 4.35 ChemAxon
LogS -4.49 ALOGPS
pKa (strongest acidic) 4.56 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 108.37 ChemAxon
Polarizability 45.52 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021953
KNApSAcK ID Not Available
Chemspider ID 2338365 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00328 Link_out
Metagene Link HMDB00328 Link_out
METLIN ID 5317 Link_out
PubChem Compound 3080612 Link_out
PDB ID Not Available
ChEBI ID 803536 Link_out
References
Synthesis Reference Suzuki, Yoshinori; Okamura, Akio; Shimomura, Kazuo; Suzuki, Tadayuki. Purification of bile acids. Jpn. Kokai Tokkyo Koho (1985), 6 pp.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Reddy B, Engle A, Katsifis S, Simi B, Bartram HP, Perrino P, Mahan C: Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects. Cancer Res. 1989 Aug 15;49(16):4629-35. Pubmed: 2545348 Link_out
  2. Barker GM, Radley S, Bain I, Davis A, Lawson AM, Keighley MR, Neoptolemos JP: Biliary bile acid profiles in patients with familial adenomatous polyposis before and after colectomy. Br J Surg. 1994 Mar;81(3):441-4. Pubmed: 8173925 Link_out
  3. Andersen E, Karlaganis G, Sjovall J: Altered bile acid profiles in duodenal bile and urine in diabetic subjects. Eur J Clin Invest. 1988 Apr;18(2):166-72. Pubmed: 3133222 Link_out
Enzymes
Name: Gastrotropin
Reactions:
    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:
    • --- []
    Gene Name: SLCO1B3
    Uniprot ID: Q9NPD5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Solute carrier organic anion transporter family member 1B1
    Reactions:
    • --- []
    Gene Name: SLCO1B1
    Uniprot ID: Q9Y6L6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Canalicular multispecific organic anion transporter 2
    Reactions:
    • --- []
    Gene Name: ABCC3
    Uniprot ID: O15438 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Bile salt export pump
    Reactions:
    • --- []
    Gene Name: ABCB11
    Uniprot ID: O95342 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ileal sodium/bile acid cotransporter
    Reactions:
    • --- []
    Gene Name: SLC10A2
    Uniprot ID: Q12908 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sodium/bile acid cotransporter
    Reactions:
    • --- []
    Gene Name: SLC10A1
    Uniprot ID: Q14973 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Solute carrier organic anion transporter family member 1A2
    Reactions:
    • --- []
    Gene Name: SLCO1A2
    Uniprot ID: P46721 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Solute carrier organic anion transporter family member 4A1
    Reactions:
    • --- []
    Gene Name: SLCO4A1
    Uniprot ID: Q96BD0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA