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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:09 UTC
HMDB IDHMDB0001421
Secondary Accession Numbers
  • HMDB01421
Metabolite Identification
Common Name4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol
Description4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol, also known as 32-ketolanosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752200
Synonyms
ValueSource
4,4-Dimethyl-14-alpha-formyl-5-alpha-cholesta-8,24-dien-3-beta-olHMDB
32-KetolanosterolHMDB
32-OxolanosterolHMDB
Chemical FormulaC30H48O2
Average Molecular Weight440.7009
Monoisotopic Molecular Weight440.36543078
IUPAC Name(2S,5S,11S,14R,15R)-5-hydroxy-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-11-carbaldehyde
Traditional Name(2S,5S,11S,14R,15R)-5-hydroxy-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-11-carbaldehyde
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C30H48O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,19,21-22,25-26,32H,8,10-18H2,1-7H3/t21-,22-,25?,26+,28-,29-,30-/m1/s1
InChI KeyPGGIMLIQOHYFIS-DHVLVQQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
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 Solubility0.0012 g/LALOGPS
logP6.74ALOGPS
logP6.74ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.34 m³·mol⁻¹ChemAxon
Polarizability55.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.29231661259
DarkChem[M-H]-202.29831661259
AllCCS[M+H]+214.91332859911
AllCCS[M-H]-214.33632859911
DeepCCS[M-2H]-249.87630932474
DeepCCS[M+Na]+224.75830932474
AllCCS[M+H]+214.932859911
AllCCS[M+H-H2O]+213.132859911
AllCCS[M+NH4]+216.632859911
AllCCS[M+Na]+217.032859911
AllCCS[M-H]-214.332859911
AllCCS[M+Na-2H]-216.532859911
AllCCS[M+HCOO]-219.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol[H][C@@]1(CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3)[C@H](C)CCC=C(C)C2936.7Standard polar33892256
4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol[H][C@@]1(CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3)[C@H](C)CCC=C(C)C3441.6Standard non polar33892256
4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol[H][C@@]1(CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3)[C@H](C)CCC=C(C)C3520.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(C)(C)C1CC33464.8Semi standard non polar33892256
4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)C1CC33686.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-1106900000-7aab9771b01bd8d000562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol GC-MS (1 TMS) - 70eV, Positivesplash10-000t-3001900000-f134e72d3582d21e06642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-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 - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 10V, Positive-QTOFsplash10-00dl-0002900000-c7cb7f642c57069745e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 20V, Positive-QTOFsplash10-0603-4129600000-5a26eeaec1a5089583d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 40V, Positive-QTOFsplash10-0ldj-6649400000-c2692444f2f4c879237e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 10V, Negative-QTOFsplash10-000i-0000900000-6613d7f8db1fcde9fb272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 20V, Negative-QTOFsplash10-000i-0000900000-d015bfee408f8bafb7a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 40V, Negative-QTOFsplash10-05fs-1015900000-2b86fef05c75c40eb7bc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 10V, Positive-QTOFsplash10-0006-3009600000-e0b58da327ec6d173a772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 20V, Positive-QTOFsplash10-0pvm-9017000000-91a8efb0b609c6db55e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 40V, Positive-QTOFsplash10-006w-7396000000-6682c890c67ce46be46b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 10V, Negative-QTOFsplash10-000i-0000900000-bdfe62598d8cbf35f2e92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 20V, Negative-QTOFsplash10-000i-0000900000-d8c7ab0b67c428c111552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol 40V, Negative-QTOFsplash10-052s-0013900000-d1c647bfbc1a10924eb42021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB022612
KNApSAcK IDNot Available
Chemspider ID117524
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6233
PubChem Compound133187
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. Saucier SE, Kandutsch AA, Phirwa S, Spencer TA: Accumulation of regulatory oxysterols, 32-oxolanosterol and 32-hydroxylanosterol in mevalonate-treated cell cultures. J Biol Chem. 1987 Oct 15;262(29):14056-62. [PubMed:3654653 ]