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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:20:19 UTC
Update Date2022-03-07 02:51:21 UTC
HMDB IDHMDB0012166
Secondary Accession Numbers
  • HMDB12166
Metabolite Identification
Common Name4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol
Description4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and it can be generated from the enzymatic carboxylation of 5alpha-cholesta-8-en-3-one. It is also a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.
Structure
Data?1582753022
Synonyms
ValueSource
4a-Carboxy-5a-cholesta-8-en-3b-olGenerator
4Α-carboxy-5α-cholesta-8-en-3β-olGenerator
4a-Carboxy-5a-cholesta-8-en-3beta-olHMDB
4alpha-Carboxy-5alpha-cholesta-8-en-3b-olHMDB
(2S,5S,6S,15R)-5-Hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylateGenerator
Chemical FormulaC28H46O3
Average Molecular Weight430.663
Monoisotopic Molecular Weight430.344695338
IUPAC Name(2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
Traditional Name(2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O
InChI Identifier
InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1
InChI KeyRODBXVVNKJCWQR-KLZNZPMLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Steroid acid
  • 4-carboxy steroid
  • 3-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP6.2ALOGPS
logP6.45ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.44 m³·mol⁻¹ChemAxon
Polarizability53.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.50531661259
DarkChem[M-H]-200.00131661259
DeepCCS[M-2H]-241.97830932474
DeepCCS[M+Na]+217.60930932474
AllCCS[M+H]+210.232859911
AllCCS[M+H-H2O]+208.332859911
AllCCS[M+NH4]+212.032859911
AllCCS[M+Na]+212.532859911
AllCCS[M-H]-207.732859911
AllCCS[M+Na-2H]-209.832859911
AllCCS[M+HCOO]-212.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-olCC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O3392.8Standard polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-olCC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O3292.4Standard non polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-olCC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O3465.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TMS,isomer #1CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C(=O)O)C1CC33520.0Semi standard non polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TMS,isomer #2CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](C(=O)O[Si](C)(C)C)C1CC33462.2Semi standard non polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,2TMS,isomer #1CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)C1CC33461.6Semi standard non polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TBDMS,isomer #1CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)C1CC33749.5Semi standard non polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,1TBDMS,isomer #2CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C1CC33721.6Semi standard non polar33892256
4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol,2TBDMS,isomer #1CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C1CC33940.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0j4i-1009500000-d0500fdc254a799c072d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (2 TMS) - 70eV, Positivesplash10-08fr-3101390000-46cdde9e4e8648d633012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 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 - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOFsplash10-03e9-0004900000-3407ec9be563d9b7ca262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOFsplash10-03xs-3019400000-d27da2a126830b00ff9d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOFsplash10-066u-6239200000-f3726ed20f097b0424ea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOFsplash10-004i-0004900000-77d8d1520aaeaa4fd3882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOFsplash10-00n0-0009500000-1fbb5a29da673f0e742a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOFsplash10-014i-1009100000-5ad9f534d16a48a405c12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOFsplash10-004r-0008900000-250dce703c733254dfb52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOFsplash10-000i-0009000000-eddf0611bb25b50405f82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOFsplash10-014r-0009000000-8175a5e0027417e0b0ce2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOFsplash10-001i-0005900000-f3b4f582c488040940692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOFsplash10-06a3-6259400000-4c8ff808d75df1d512092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOFsplash10-0aov-9213000000-7b6183a193d666f727d22021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothInflammatory bowel disease details
Associated Disorders and Diseases
Disease References
Inflammatory bowel disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028820
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25200718
PDB IDNot Available
ChEBI IDNot Available
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. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
  6. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  8. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..