MiMeDB: Showing metabocard for Lanosterin (MMDBc0032951)

Microbial

Human

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:28:36 UTC

Update Date

2025-01-15 18:57:26 UTC

Metabolite ID

MMDBc0032951

Metabolite Identification

Common Name

Lanosterin

Description

Lanosterol, 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

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₃₀H₅₀O

Average Mass

426.7174

Monoisotopic Mass

426.3861662

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

79-63-0

SMILES

Not Available

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 Key

CAHGCLMLTWQZNJ-BQNIITSRSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	285.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-24	45.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	758.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1207.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1174.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	863.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3609.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	97.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	353.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1158.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	837.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	332.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	335.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	9.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	342.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	652.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	615.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	2060.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	2250.8

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Lanosterin_TMS_1	CC(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]1CC3	standard non polar	2025-10-24	1200.69
Gas Chromatography	Lanosterin_TMS_1	CC(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]1CC3	standard polar	2025-10-24	2278.53

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191935	Lanosterol 14-alpha demethylase	Unknown	Q16850	Homo sapiens
MMDBp0192096	Lanosterol synthase	Enzyme	P48449	Homo sapiens
MMDBp0193337	Delta(24)-sterol reductase	Unknown	Q15392	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Bloch Pathway (Cholesterol Biosynthesis)
Kandutsch-Russell Pathway (Cholesterol Biosynthesis)
Mevalonate Pathway

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019910	Lanosterin	24,25-dihydrolanosterol	Unknown Protein		PathBank	31602464
MMDBr0019911	Lanosterin	Formic acid	Lanosterol 14-alpha demethylase CYP51	Demethylation	PathBank	31602464
MMDBr0024914	Lanosterin	CoA	Sterol O-acyltransferase 1	Acylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	9	Human feces; Human saliva	Unknown
Bacteria/Eubacteria	Proteobacteria	50	Human feces; Human sputum; Human ; Human unknown	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	25	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	15	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.48	0.114	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for Lanosterin (MMDBc0032951)

MOL for #<Metabolite:0x00007f2e2c96daa0>

3D MOL for #<Metabolite:0x00007f2e2c96daa0>

3D SDF for #<Metabolite:0x00007f2e2c96daa0>

3D-SDF for #<Metabolite:0x00007f2e2c96daa0>

PDB for #<Metabolite:0x00007f2e2c96daa0>

3D PDB for #<Metabolite:0x00007f2e2c96daa0>

SMILES for #<Metabolite:0x00007f2e2c96daa0>

INCHI for #<Metabolite:0x00007f2e2c96daa0>

Structure for #<Metabolite:0x00007f2e2c96daa0>

3D Structure for #<Metabolite:0x00007f2e2c96daa0>