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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:15 UTC
HMDB IDHMDB0000503
Secondary Accession Numbers
  • HMDB00503
  • HMDB0062796
  • HMDB62796
Metabolite Identification
Common Name7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid
Description7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid, also known as 3-dehydrochenodeoxycholic acid or (5beta,7alpha)-7-hydroxy-3-oxocholan-24-oate, is classified as a monohydroxy bile acids, alcohol or a monohydroxy bile acids, alcohol derivative. Monohydroxy bile acids, alcohols are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is considered to be practically insoluble (in water) and acidic. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is a bile acid lipid molecule. Glycine- and taurine-conjugated 7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid has been identified in normal human serum (PMID: 1939467 ) and as a cholesterol metabolite in bile acids produced in HepG2 cells, a well-differentiated human hepatoblastoma cell line (PMID: 1655725 ).
Structure
Data?1582752135
Synonyms
ValueSource
(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oic acidChEBI
3-Dehydrochenodeoxycholic acidChEBI
3-Oxochenodeoxycholic acidChEBI
Dehydrochenodeoxycholic acidChEBI
(5b,7a)-7-Hydroxy-3-oxocholan-24-OateGenerator
(5b,7a)-7-Hydroxy-3-oxocholan-24-Oic acidGenerator
(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-OateGenerator
(5Β,7α)-7-hydroxy-3-oxocholan-24-OateGenerator
(5Β,7α)-7-hydroxy-3-oxocholan-24-Oic acidGenerator
3-DehydrochenodeoxycholateGenerator
3-OxochenodeoxycholateGenerator
DehydrochenodeoxycholateGenerator
7a-Hydroxy-3-oxo-5b-cholan-24-OateGenerator
7a-Hydroxy-3-oxo-5b-cholan-24-Oic acidGenerator
7alpha-Hydroxy-3-oxo-5beta-cholan-24-OateGenerator
7Α-hydroxy-3-oxo-5β-cholan-24-OateGenerator
7Α-hydroxy-3-oxo-5β-cholan-24-Oic acidGenerator
7Α-hydroxy-3-oxo-5β-cholanic acidHMDB
3-oxo-7Α-hydroxy-5β-cholanic acidHMDB
3-oxo-7Α-hydroxycholan-24-Oic acidHMDB
3-Keto-7α-hydroxy-5β-cholanic acidHMDB
7Α-hydroxy-3-oxo-5β-cholanoic acidHMDB
7a-Hydroxy-3-oxo-5b-cholanoic acidHMDB
7alpha-Hydroxy-3-oxo-5beta-cholanoic acidHMDB
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
Chemical FormulaC24H38O4
Average Molecular Weight390.564
Monoisotopic Molecular Weight390.277009704
IUPAC Name(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number4185-00-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChI KeyKNVADAPHVNKTEP-CIGXQKLNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 7-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88 - 90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.11ALOGPS
logP3.92ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.25 m³·mol⁻¹ChemAxon
Polarizability45.49 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0009000000-fafd5a671c61f81c15c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-076s-0009000000-70b658ddea6d96ced853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-1319000000-ef02c40883611a4c3308Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-bcd0337fb08276e5242bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0009000000-fb7ca64898cc60921257Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-c936cb19bcd9e5afce3cSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022081
KNApSAcK IDNot Available
Chemspider ID4447020
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283932
PDB IDNot Available
ChEBI ID88097
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceRiva, Sergio; Bovara, Roberto; Zetta, Lucia; Pasta, Piero; Ottolina, Gianluca; Carrea, Giacomo. Enzymic a/b inversion of C-3 hydroxyl of bile acids and study of the effects of organic solvents on reaction rates. Journal of Organic Chemistry (1988), 53(1), 88-92.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Axelson M, Mork B, Everson GT: Bile acid synthesis in cultured human hepatoblastoma cells. J Biol Chem. 1991 Sep 25;266(27):17770-7. [PubMed:1655725 ]
  2. Goto J, Saisho Y, Nambara T: Studies on steroids. CCLII. Separation and characterization of 3-oxobile acids in serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1991 Jul 5;567(2):343-9. [PubMed:1939467 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in binding
Specific function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular weight:
14371.2
References
  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular weight:
37697.4
References
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular weight:
77192.5