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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-07-13 12:46:54 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0012454
Secondary Accession Numbers
  • HMDB0062211
  • HMDB12454
  • HMDB62211
Metabolite Identification
Common Name3beta,7alpha-Dihydroxy-5-cholestenoate
Description3beta,7alpha-Dihydroxy-5-cholestenoate, also known as 3b,7a-dihydroxy-5-cholesten-26-Oic acid, 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. 3beta,7alpha-Dihydroxy-5-cholestenoate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3beta,7alpha-Dihydroxy-5-cholestenoate is a potentially toxic compound.
Structure
Data?1582753056
Synonyms
ValueSource
3beta,7alpha-Dihydroxy-5-cholesten-26-Oic acidKegg
3b,7a-Dihydroxy-5-cholesten-26-OateGenerator
3b,7a-Dihydroxy-5-cholesten-26-Oic acidGenerator
3beta,7alpha-Dihydroxy-5-cholesten-26-OateGenerator
3Β,7α-dihydroxy-5-cholesten-26-OateGenerator
3Β,7α-dihydroxy-5-cholesten-26-Oic acidGenerator
3b,7a-Dihydroxy-5-cholestenoateGenerator
3b,7a-Dihydroxy-5-cholestenoic acidGenerator
3beta,7alpha-Dihydroxy-5-cholestenoic acidGenerator
3Β,7α-dihydroxy-5-cholestenoateGenerator
3Β,7α-dihydroxy-5-cholestenoic acidGenerator
3,7-Dihydroxy-5-cholestenoic acidHMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oic acidHMDB
Chemical FormulaC27H44O4
Average Molecular Weight432.645
Monoisotopic Molecular Weight432.323959897
IUPAC Name(6R)-6-[(1S,2R,5S,9S,10S,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(1S,2R,5S,9S,10S,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid
CAS Registry Number115538-84-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C27H44O4/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/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1
InChI KeyGYJSAWZGYQXRBS-GRJZKGIBSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen 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 Solubility0.0069 g/LALOGPS
logP10(3.92) g/LALOGPS
logP10(4.9) g/LChemAxon
logS10(-4.8) g/LALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.75 m³·mol⁻¹ChemAxon
Polarizability52.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3beta,7alpha-Dihydroxy-5-cholestenoate,1TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O3651.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,1TMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O3664.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,1TMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C3574.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,2TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O3557.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,2TMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C3556.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,2TMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C3584.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,3TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C3488.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,1TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O3875.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,1TBDMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O3870.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,1TBDMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C(C)(C)C3845.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,2TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O3986.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,2TBDMS,#2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C(C)(C)C4043.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,2TBDMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C(C)(C)C4053.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
3beta,7alpha-Dihydroxy-5-cholestenoate,3TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(=O)O[Si](C)(C)C(C)(C)C4181.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v4r-0247900000-6844e920e0f45971085c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1110149000-9481ac260199d7f5b5422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3beta,7alpha-Dihydroxy-5-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 - 3beta,7alpha-Dihydroxy-5-cholestenoate 10V, Positive-QTOFsplash10-014j-0007900000-ba51b1e65739e23c2f832017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 20V, Positive-QTOFsplash10-014j-0009200000-ad2af6637f0b3ce7d6742017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 40V, Positive-QTOFsplash10-014i-2119000000-87d5606a65d11c0d0bc22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 10V, Negative-QTOFsplash10-001i-0001900000-11d955c76d3b48e698822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 20V, Negative-QTOFsplash10-02ar-0007900000-1344438f254eaafa390d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 40V, Negative-QTOFsplash10-0600-6009200000-7340abd91104a8c2fb9b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 10V, Positive-QTOFsplash10-00ls-1106900000-2985a04589bff796de8f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 20V, Positive-QTOFsplash10-01ba-2159100000-99496085551528fe3dce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 40V, Positive-QTOFsplash10-052s-7690000000-313265b61c2dcc7ed0402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 10V, Negative-QTOFsplash10-001i-0000900000-3cca5453e09966b932ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 20V, Negative-QTOFsplash10-001i-0002900000-acd26e8db7d05ca4d8582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3beta,7alpha-Dihydroxy-5-cholestenoate 40V, Negative-QTOFsplash10-004i-1002900000-97654ceb214ce880e5832021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.1 uMInfant (0-1 year old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified25.4 uMInfant (0-1 year old)Not SpecifiedD-Bifunctional Protein Deficiency details
BloodDetected and Quantified0.005 uMNewborn (0-30 days old)Female
Rhizomelic chondrodysplasia punctata
details
BloodDetected and Quantified0.319 uMInfant (0-1 year old)Male
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified5.71 uMNewborn (0-30 days old)Not Specified
Zellweger syndrome
details
BloodDetected and Quantified0-4.500 uMChildren (1-13 years old)Female
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified0.0360-7.0300 uMNewborn (0-30 days old)Female
Peroxisomal biogenesis disorder
details
Associated Disorders and Diseases
Disease References
Rhizomelic chondrodysplasia punctata
  1. Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Peroxisomal biogenesis defect
  1. Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
D-Bifunctional protein deficiency
  1. Rizzo C, Boenzi S, Wanders RJ, Duran M, Caruso U, Dionisi-Vici C: Characteristic acylcarnitine profiles in inherited defects of peroxisome biogenesis: a novel tool for screening diagnosis using tandem mass spectrometry. Pediatr Res. 2003 Jun;53(6):1013-8. doi: 10.1203/01.PDR.0000064902.59052.0F. Epub 2003 Mar 19. [PubMed:12646728 ]
Associated OMIM IDs
  • 215100 (Rhizomelic chondrodysplasia punctata)
  • 214100 (Peroxisomal biogenesis defect)
  • 261515 (D-Bifunctional protein deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17335
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3081084
PDB IDNot Available
ChEBI ID81015
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. 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:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
3beta-Hydroxy-5-cholestenoic acid + Oxygen + NADPH + Hydrogen Ion → 3beta,7alpha-Dihydroxy-5-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