Lathosterol (BioCAD00000013242)

blood feces adipose tissue adrenal cortex adrenal gland adrenal medulla bladder brain epidermis eye lens fibroblasts intestine kidney liver neuron ovary pancreas placenta platelet prostate skeletal muscle testis plant natural products microbial natural products

Metabolite Card

Formula: C27H46O (386.3548)
SMILES: [H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

Synonyms [en]

lathosterol; 5alpha-Cholest-7-en-3beta-ol; Cholest-7-en-3beta-ol; gamma-Cholesterol; 3beta-Hydroxy-5alpha-cholest-7-ene; 7-Cholesten-3-beta-ol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Lathosterol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000013242). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID:8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O.

Extracellular Membrane Endoplasmic reticulum
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 6036-58-4
  • CAS Registry Number: 80-99-9
  • PubChem: 20111975
  • PubChem: 420
  • PubChem: 6432730
  • PubChem: 65728
  • PubChem: 9930097
  • ChEBI: ChEBI:17168
  • HMDB: HMDB0001170
  • LipidMaps: LMST01010089
  • KEGG: C01189
  • BioCyc: CPD-4186
  • NCBI MeSH: lathosterol
  • Wikipedia: Lathosterol
  • RefMet: RM0028095
  • Metlin: METLIN_166
  • Coconut NaturalProduct: CNP0115532.2
  • Coconut NaturalProduct: CNP0115532.4

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03353 5.3.3.5 5alpha-cholest-7-en-3beta-ol delta7-delta8-isomerase
KEGG:R04328 1.1.1.170 C01189 + C00011 + 4 C00001 + 3 C00006<=>C05111 + 3 C00007 + 3 C00005 + 3 C00080
KEGG:R05703 1.3.1.72 lanosterol D24-reductase
KEGG:R07215 1.14.19.20 lathosterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating
Rhea:RHEA:13686 1.3.1.72 lathosterol + NADP+ => 5α-cholesta-7,24-dien-3β-ol + NADPH + H+
Rhea:RHEA:13687 1.3.1.72 5α-cholesta-7,24-dien-3β-ol + NADPH + H+ => lathosterol + NADP+
Rhea:RHEA:13688 1.3.1.72 lathosterol + NADP+ <=> 5α-cholesta-7,24-dien-3β-ol + NADPH + H+
Rhea:RHEA:15282 5.3.3.5 lathosterol => 5α-cholest-8-en-3β-ol
Rhea:RHEA:15283 5.3.3.5 5α-cholest-8-en-3β-ol => lathosterol
Rhea:RHEA:15284 5.3.3.5 lathosterol <=> 5α-cholest-8-en-3β-ol
Rhea:RHEA:35464 lathosterol + NAD+ => 5α-cholest-7-en-3-one + NADH + H+
Rhea:RHEA:35465 5α-cholest-7-en-3-one + NADH + H+ => lathosterol + NAD+
Rhea:RHEA:35466 lathosterol + NAD+ <=> 5α-cholest-7-en-3-one + NADH + H+
Rhea:RHEA:46557 1.14.19.20 lathosterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ => 7-dehydrocholesterol + 2 Fe(III)-[cytochrome b5] + 2 H2O
Rhea:RHEA:46558 1.14.19.20 7-dehydrocholesterol + 2 Fe(III)-[cytochrome b5] + 2 H2O => lathosterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+
Rhea:RHEA:46559 1.14.19.20 lathosterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ <=> 7-dehydrocholesterol + 2 Fe(III)-[cytochrome b5] + 2 H2O
Rhea:RHEA:53253 lathosterol + reduced [NADPH—hemoprotein reductase] + O2 => 5α-cholestan-7-oxo-3β-ol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:53254 5α-cholestan-7-oxo-3β-ol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => lathosterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:53255 lathosterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 5α-cholestan-7-oxo-3β-ol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:53257 lathosterol + reduced [NADPH—hemoprotein reductase] + O2 => 7α,8α-epoxy-5α-cholestan-3β-ol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
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Organism Source

Taxonomy Source

  1. Blastocladia ramosa [ncbi taxid: 945685]
  2. Carya illinoinensis [ncbi taxid: 32201]
  3. Dictyuchus monosporus [ncbi taxid: 120407]
  4. Laetia procera [ncbi taxid: ]
  5. Nectria galligena [ncbi taxid: ]
  6. Taraxacum obovatum [ncbi taxid: 90041]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY66-5 superpathway of cholesterol biosynthesis
BioCyc:HUMAN_PWY66-341 cholesterol biosynthesis I
BioCyc:META_PWY66-341 cholesterol biosynthesis I
BioCyc:HUMAN_PWY66-3 cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
BioCyc:META_PWY66-3 cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
BioCyc:META_PWY66-5 superpathway of cholesterol biosynthesis
Plant Reactome:R-HVU-1119286 Cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-TAE-1119286 Cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-TDI-3906998 Fatty acid and lipid metabolism
Plant Reactome:R-OGU-3906998 Fatty acid and lipid metabolism
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-1119286 Cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PVU-2744345 Metabolism and regulation
Plant Reactome:R-PVU-3906998 Fatty acid and lipid metabolism
Plant Reactome:R-BNA-3906998 Fatty acid and lipid metabolism
View All Pathways