Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:09 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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.75331661259
DarkChem[M-H]-200.46331661259
AllCCS[M+H]+215.07332859911
AllCCS[M-H]-214.83332859911
DeepCCS[M-2H]-248.51630932474
DeepCCS[M+Na]+222.94930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lanosterol[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)C3166.6Standard polar33892256
Lanosterol[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)C3305.8Standard non polar33892256
Lanosterol[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)C3334.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lanosterol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]1CC33371.9Semi standard non polar33892256
Lanosterol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC33578.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Lanosterol GC-MS (1 TMS)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Lanosterol EI-B (Non-derivatized)splash10-03dl-2953300000-ae1832f19369485ff53c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Lanosterol EI-B (Non-derivatized)splash10-0aou-9820200000-573525b346ad3c9eef592017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Lanosterol GC-MS (Non-derivatized)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Lanosterol GC-EI-TOF (Non-derivatized)splash10-0a4l-2910000000-c67a1f122f33698a14f62017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lanosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1009400000-e2b516142f5128a7b5f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lanosterol GC-MS (1 TMS) - 70eV, Positivesplash10-001i-3002900000-35e63c0bf6f033cb847c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lanosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lanosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05mo-9731200000-b1bc6bb68e352e3bd6872015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol n/a 1V, positive-QTOFsplash10-0a6r-0110900000-5e42e1f2d9ad534c003c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 13V, positive-QTOFsplash10-0a4i-0230900000-10f58fa6e118cd7c59972020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 17V, positive-QTOFsplash10-0a4i-1791800000-178153ad92eececb33c42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 20V, positive-QTOFsplash10-0a4i-2980300000-6ce95c7f8b15b35475af2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 23V, positive-QTOFsplash10-0a4j-2950100000-48f86ff7a22c596aa44d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 27V, positive-QTOFsplash10-0592-3940000000-c35d0cb6a2e4e291e8f82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 30V, positive-QTOFsplash10-0592-3920000000-d717fdd3322a881bef992020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 34V, positive-QTOFsplash10-0592-4910000000-4c6d07e3a8e48ae885802020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 41V, positive-QTOFsplash10-0a4j-5900000000-4c8b72037dbeae9a46d12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 52V, positive-QTOFsplash10-067m-8900000000-522b8688d50362297c412020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 62V, positive-QTOFsplash10-0aou-9700000000-70d433827c1a6dab0c412020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 76V, positive-QTOFsplash10-05ox-9500000000-5b122dea636d3e3b59162020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 90V, positive-QTOFsplash10-05r3-9500000000-0c1c5cbd994f8406f30e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol Orbitrap 111V, positive-QTOFsplash10-05r3-9600000000-5cb8ae11d071fa19f2062020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol n/a 29V, positive-QTOFsplash10-0ktf-0392000000-03cda521ce6e102d92e42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol n/a 29V, positive-QTOFsplash10-059j-2900000000-8086693fb040e5ed75012020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol n/a 29V, positive-QTOFsplash10-0a4i-4900000000-c58ff2dc28c6ba6399972020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol n/a 29V, positive-QTOFsplash10-01vk-0900000000-805937445cceda0cd70a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lanosterol n/a 29V, positive-QTOFsplash10-0aor-0900000000-22d304b445b737121aa72020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lanosterol 10V, Positive-QTOFsplash10-0a6r-0002900000-2cfcf7ce4b5b21140eae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lanosterol 20V, Positive-QTOFsplash10-0pdi-2139500000-9a25961000db9796d6da2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lanosterol 40V, Positive-QTOFsplash10-0uxr-4259100000-9f7f26265abec4122e352016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lanosterol 10V, Negative-QTOFsplash10-004i-0000900000-77a57cecc2069bee19262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lanosterol 20V, Negative-QTOFsplash10-004i-0000900000-5b0f06bf8120e780e30c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lanosterol 40V, Negative-QTOFsplash10-0a4l-1009400000-421e305d47b29da427d22016-08-03Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDNot Available
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