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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-03-13 17:11:58 UTC
HMDB IDHMDB0001251
Secondary Accession Numbers
  • HMDB0001323
  • HMDB0001462
  • HMDB01251
  • HMDB01323
  • HMDB01462
Metabolite Identification
Common NameLanosterol
DescriptionLanosterol, also known as lanosterin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, lanosterol is considered to be a sterol lipid molecule. Lanosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lanosterol is biochemically synthesized starting from acetyl-CoA by the HMG-CoA reductase pathway. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide.
Structure
Data?1584119518
Synonyms
ValueSource
(3beta)-Lanosta-8,24-dien-3-olChEBI
(3beta,5alpha)-4,4,14-Trimethylcholesta-8,24-dien-3-olChEBI
4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b)-Lanosta-8,24-dien-3-olGenerator
(3β)-Lanosta-8,24-dien-3-olGenerator
(3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-olGenerator
(3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-olGenerator
4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-olGenerator
4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-olGenerator
(3 beta)-Lanosta-8,24-dien-3-olHMDB
(3alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-olHMDB
(3beta,5alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-olHMDB
Botalan base 138HMDB
Lanosta-8,24-dien-3-olHMDB
Lanosta-8,24-dien-3beta-olHMDB
Lanosta-8,24-dienolHMDB
LanosterolHMDB
LansterHMDB
4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-olMeSH, HMDB
KryptosterolMeSH, HMDB
LanosterinChEBI
3beta-Hydroxy-lansota-8,24-dien-21-oic acidHMDB
3beta-Hydroxylanosta-8,24-dieneHMDB
3β-Hydroxy-lansota-8,24-dien-21-oic acidHMDB
3β-Hydroxylanosta-8,24-dieneHMDB
4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-olHMDB
4,4,14α-Trimethylcholesta-8,24-dien-3β-olHMDB
5alpha-Lanosta-8,24-dien-3beta-olHMDB
5α-Lanosta-8,24-dien-3β-olHMDB
Lanosta-8,24-dien-3β-olHMDB
Lanostadien-3beta-olHMDB
Lanostadien-3β-olHMDB
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number79-63-0
SMILES
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
InChI KeyCAHGCLMLTWQZNJ-BQNIITSRSA-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
  • 14-alpha-methylsteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP7.72ALOGPS
logP7.71ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity134.54 m³·mol⁻¹ChemAxon
Polarizability55.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-2953300000-ae1832f19369485ff53cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aou-9820200000-573525b346ad3c9eef59Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-2910000000-c67a1f122f33698a14f6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1009400000-e2b516142f5128a7b5f6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-3002900000-35e63c0bf6f033cb847cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0a6r-0110900000-5e42e1f2d9ad534c003cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0a4i-0230900000-10f58fa6e118cd7c5997Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-1791800000-178153ad92eececb33c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0a4i-2980300000-6ce95c7f8b15b35475afSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-0a4j-2950100000-48f86ff7a22c596aa44dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0592-3940000000-c35d0cb6a2e4e291e8f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-0592-3920000000-d717fdd3322a881bef99Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-0592-4910000000-4c6d07e3a8e48ae88580Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0a4j-5900000000-4c8b72037dbeae9a46d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-067m-8900000000-522b8688d50362297c41Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 62V, positivesplash10-0aou-9700000000-70d433827c1a6dab0c41Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-05ox-9500000000-5b122dea636d3e3b5916Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, positivesplash10-05r3-9500000000-0c1c5cbd994f8406f30eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 111V, positivesplash10-05r3-9600000000-5cb8ae11d071fa19f206Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0ktf-0392000000-03cda521ce6e102d92e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-059j-2900000000-8086693fb040e5ed7501Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0a4i-4900000000-c58ff2dc28c6ba639997Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-01vk-0900000000-805937445cceda0cd70aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0aor-0900000000-22d304b445b737121aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-2cfcf7ce4b5b21140eaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-2139500000-9a25961000db9796d6daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-4259100000-9f7f26265abec4122e35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-77a57cecc2069bee1926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-5b0f06bf8120e780e30cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-421e305d47b29da427d2Spectrum
MSMass Spectrum (Electron Ionization)splash10-05mo-9731200000-b1bc6bb68e352e3bd687Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.48 +/- 0.114 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03696
Phenol Explorer Compound IDNot Available
FooDB IDFDB013802
KNApSAcK IDC00003657
Chemspider ID216175
KEGG Compound IDC01724
BioCyc IDLANOSTEROL
BiGG ID38253
Wikipedia LinkLanosterol
METLIN ID6108
PubChem Compound246983
PDB IDNot Available
ChEBI ID16521
Food Biomarker OntologyNot Available
VMH IDLANOST
References
Synthesis ReferenceMaienthal, Millard; Franklin, Philip J. Preparation of lanosterol from bromolanosterol. Journal of Organic Chemistry (1955), 20 1627-30.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81
Reactions
Lanosterol + Oxygen + NADPH + Hydrogen Ion → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus.
Gene Name:
LSS
Uniprot ID:
P48449
Molecular weight:
83308.065
Reactions
(3S)-2,3-epoxy-2,3-dihydrosqualene → Lanosteroldetails
(S)-2,3-Epoxysqualene → Lanosteroldetails
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Lanosterol + NADPH + Hydrogen Ion → 24,25-Dihydrolanosterol + NADPdetails