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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-13 13:38:40 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0012458
Secondary Accession Numbers
  • HMDB0062430
  • HMDB12458
  • HMDB62430
Metabolite Identification
Common Name7alpha-Hydroxy-3-oxo-4-cholestenoate
Description7alpha-Hydroxy-3-oxo-4-cholestenoate, also known as 7-Hoca, is a member of the class of compounds known as monohydroxy bile acids, alcohols, and derivatives. Thes compounds are bile acids, alcohols, or any of their derivatives bearing a hydroxyl group. 7alpha-Hydroxy-3-oxo-4-cholestenoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 7alpha-Hydroxy-3-oxo-4-cholestenoate is involved in metabolic disorders such as 27-hydroxylase deficiency, familial hypercholanemia (FHCA), and Zellweger syndrome. 7alpha-Hydroxy-3-oxo-4-cholestenoate is involved in the primary bile acid biosynthesis pathway. 7alpha-Hydroxy-3-oxo-4-cholestenoate is created from either 3beta,7alpha-dihydroxy-5-cholestenoate or 7alpha,26-dihydroxy-4-cholesten-3-one through the actions of HSD3B7 (EC 1.1.1.181) or CYP27A (EC 1.14.13.15), respectively.
Structure
Data?1582753057
Synonyms
ValueSource
7-HocaChEBI
7a-Hydroxy-3-oxo-4-cholestenoateGenerator
7a-Hydroxy-3-oxo-4-cholestenoic acidGenerator
7alpha-Hydroxy-3-oxo-4-cholestenoic acidGenerator
7Α-hydroxy-3-oxo-4-cholestenoateGenerator
7Α-hydroxy-3-oxo-4-cholestenoic acidGenerator
7 alpha-Hydroxy-3-oxo-4-cholestenoic acidHMDB
(7Α)-7-hydroxy-3-oxocholest-4-en-26-Oic acidHMDB
(7Α)-7-hydroxy-3-oxocholest-4-en-26-OateHMDB
7Α-hydroxy-3-oxocholest-4-en-26-Oic acidHMDB
(7alpha)-7-Hydroxy-3-oxocholest-4-en-26-Oic acidHMDB
(7alpha)-7-Hydroxy-3-oxocholest-4-en-26-OateHMDB
7alpha-Hydroxy-3-oxocholest-4-en-26-Oic acidHMDB
7-alpha-Hydroxy-3-oxo-4-cholestenoateHMDB
7alpha-Hydroxy-3-oxo-4-cholestenoateHMDB, Generator
Chemical FormulaC27H42O4
Average Molecular Weight430.629
Monoisotopic Molecular Weight430.308309832
IUPAC Name(6R)-6-[(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-methylheptanoic acid
CAS Registry Number115538-85-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C27H42O4/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/h14,16-17,20-24,29H,5-13,15H2,1-4H3,(H,30,31)/t16-,17?,20-,21+,22+,23-,24+,26+,27-/m1/s1
InChI KeySATGKQGFUDXGAX-MYWFJNCASA-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
  • Steroid acid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Medium-chain fatty acid
  • Cyclohexenone
  • Hydroxy fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0038 g/LALOGPS
logP10(4.05) g/LALOGPS
logP10(5.31) g/LChemAxon
logS10(-5.1) g/LALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.85 m³·mol⁻¹ChemAxon
Polarizability51.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7alpha-Hydroxy-3-oxo-4-cholestenoate,1TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C)C(=O)O3730.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,1TMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O)C(=O)O[Si](C)(C)C3728.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,1TMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O)C(=O)O3689.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,2TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C)C(=O)O[Si](C)(C)C3642.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,2TMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C)C(=O)O3549.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,2TMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O)C(=O)O[Si](C)(C)C3603.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,1TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O3947.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,1TBDMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O)C(=O)O[Si](C)(C)C(C)(C)C3968.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,1TBDMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O)C(=O)O3913.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,2TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C4109.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,2TBDMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O3982.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7alpha-Hydroxy-3-oxo-4-cholestenoate,2TBDMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O)C(=O)O[Si](C)(C)C(C)(C)C4069.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 10V, Positive-QTOFsplash10-03e9-0005900000-b7bca15cabd9e12c66962019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 20V, Positive-QTOFsplash10-029j-1009300000-55f0578d6b1582318cfc2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 40V, Positive-QTOFsplash10-014i-3219000000-f33373cace65dac79a132019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 10V, Negative-QTOFsplash10-004i-0001900000-ad4ad49ae3c3a393e0e82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 20V, Negative-QTOFsplash10-02dr-0007900000-88a170ea510b330ee78d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 40V, Negative-QTOFsplash10-0avi-6009200000-78baf4ea8fd63c3606622019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 10V, Negative-QTOFsplash10-004i-0000900000-2c11db7f4225ffd58c752021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 20V, Negative-QTOFsplash10-004i-0007900000-319ad83ee01108cd0a352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 40V, Negative-QTOFsplash10-004i-2003900000-183aa10ccc1b913cc96d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 10V, Positive-QTOFsplash10-001i-0004900000-6dd1885d6034e79dff912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 20V, Positive-QTOFsplash10-000i-3289300000-c62c18e4c41396c105792021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-Hydroxy-3-oxo-4-cholestenoate 40V, Positive-QTOFsplash10-059j-5971000000-425901eed2cf0114ca5a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID2338765
KEGG Compound IDC17337
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3081085
PDB IDNot Available
ChEBI ID83036
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
7 alpha,26-Dihydroxy-4-cholesten-3-one + Oxygen + NADPH + Hydrogen Ion → 7alpha-Hydroxy-3-oxo-4-cholestenoate + NADP + Waterdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265
Reactions
3beta,7alpha-Dihydroxy-5-cholestenoate + NAD → 7alpha-Hydroxy-3-oxo-4-cholestenoate + NADH + Hydrogen Iondetails