(Q3024529)

cholesterol biosynthetic process via desmosterol

inferred from SMILES

part of

subject has role

reaction intermediate

1 reference

Gene Ontology release 2020-05-02

fucosterol-epoxide lyase activity

1 reference

Gene Ontology release 2020-05-02

Rhea release 113

chemical structure

Desmosterol.png
1,237 × 888; 17 KB

0 references

image of molecular model or crystal lattice model

Desmosterol 3D ball.png
2,000 × 1,202; 392 KB

depicts

ball-and-stick model

0 references

mass

384.339216 dalton

1 reference

DESMOSTEROL (English)

(3S,8R,9R,10R,13R,14R,17R)-10,13-dimethyl-17-[(2S)-6-methylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

3 October 2016

stereoisomer of

2 references

inferred from InChIKey

inferred from InChI

chemical formula

C₂₇H₄₄O

1 reference

DESMOSTEROL (English)

3 October 2016

canonical SMILES

CC(CCC=C(C)C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C

1 reference

DESMOSTEROL (English)

3 October 2016

isomeric SMILES

C[C@H](CCC=C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C

1 reference

Recon 2.2: from reconstruction to model of human metabolism

DESMOSTEROL (English)

3 October 2016

2 references

A community-driven global reconstruction of human metabolism.

Leptogorgia piccola

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Ellisella paraplexauroides

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Eunicella labiata

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Leptogorgia ruberrima

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Leptogorgia viminalis

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Leptogorgia violetta

1 reference

Sterol composition of some gorgonians from the Senegalese coast

Acarnus erithacus

1 reference

Biosynthetic studies of marine lipids-xxix. Demonstration of sterol side chain dealkylation using cell-free extracts of marine sponges

Apis mellifera

2 references

Makisterone A and 24-methylenecholesterol from the ovaries of the honey bee,Apis mellifera L

Compositions of royal jelly II. Organic acid glycosides and sterols of the royal jelly of honeybees (Apis mellifera).

Aplysina fistularis

1 reference

Biosynthetic studies of marine lipids-xxix. Demonstration of sterol side chain dealkylation using cell-free extracts of marine sponges

Bombyx mori

3 references

Letter: Stereospecificity in the conversion of fucosterol 24,28-epoxide to desmosterol in the silkworm, Bombyx mori

Mechanism of the conversion of fucosterol epoxide into desmosterol in insects. Stereochemical fate of the diastereotopic C-26 and C-27 methyl groups of the epoxide

Stereochemistry of the hydrogen addition to C-25 of desmosterol by sterol-Δ24-reductase of the silkworm, Bombyx mori

Boodleopsis pusilla

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Bryopsis plumosa

1 reference

Sterol composition of twelve chlorophyceae from the senegalese coast and their chemotaxonomic significance

Centroceras clavulatum

1 reference

Ceramium pacificum

2 references

Sterols of some red algae

Chlamydomonas reinhardtii

1 reference

Evidence for sterol side-chain dealkylation in Chlamydomonas reinhardtii

Dermonema abbottiae

1 reference

Phycochemical Studies on Dermonema abbottiae (Nemaliales — Rhodophyta)

Dichotomaria marginata

1 reference

Cytotoxic oxygenated desmosterols of the red alga Galaxaura marginata

Galaxaura marginata

1 reference

Cytotoxic oxygenated desmosterols of the red alga Galaxaura marginata

Gelidium filicinum

2 references

Sterols of some red algae

Gossypium hirsutum

1 reference

Free and esterified sterols of cotton buds and anthers

Water net

1 reference

24-Methylene-25-methylcholesterol and both C-24 epimers of 24-ethyl-22-dehydrocholesterol in a freshwater green algaHydrodictyon reticulatum

Mazzaella laminarioides

1 reference

Leucilla nuttingi

1 reference

Biosynthetic studies of marine lipids. 38. Mechanism and scope of sterol side chain dealkylation in sponges: evidence for concurrent alkylation and dealkylation

Mortierella alpina

2 references

Occurrence of a novel sterol, 24,25-methylenecholest-5-en-3β-ol, inMortierella alpina 1S-4

Phytosterol biosynthesis pathway in Mortierella alpina

Palmaria palmata

1 reference

Occurrence of steryl glycosides and acylated steryl glycosides in some marine algae

Polymastia pachymastia

1 reference

Biosynthetic studies of marine lipids-xxix. Demonstration of sterol side chain dealkylation using cell-free extracts of marine sponges

Rissoella verruculosa

1 reference

Sterols of the red alga Rissoella verruculosa

Salpa thompsoni

1 reference

Fatty acids and sterols of the tunicate, Salpa thompsoni, from the Antarctic Ocean: chemical composition and hemolytic activity

Tethya deformis

1 reference

Sterols of the spongeTethya amamensis: Occurrence of (24E)-24-ethylidenecholesta-5,7-dienol, (24E)-24-propylidenecholesta-5,7-dienol, and (24Z)-24-propylidenecholesta-5,7-dienol

Tethya aurantia

1 reference

Biosynthetic studies of marine lipids-xxix. Demonstration of sterol side chain dealkylation using cell-free extracts of marine sponges

Wrightia tinctoria

1 reference

14α-Methylzymosterol and other sterols from Wrightia tinctoria seeds

Aplysia depilans

1 reference

Sterols and sterol biosynthesis in the slug Aplysia depilans

Cymodocea nodosa

1 reference

Configuration at C-24 of sterols from the marine phanerogames Posidonia oceanica and Cymodocea nodosa

Desmarestia menziesii

1 reference

New plastoquinones from the brown alga Desmarestiamenziesii

Echinometra lucunter

1 reference

Free sterols of the sea urchin Echinometra lucunter.

Amphilectus digitatus

1 reference

Steroid compounds of marine sponges. I. Sterols ofEsperiopsis digitata

Neoesperiopsis digitata

1 reference

Steroid compounds of marine sponges. I. Sterols ofEsperiopsis digitata

Amphilectus fucorum

1 reference

Novel sterols from the sponge esperiopsis edwardii

Muricea californica

1 reference

Occurrence and seasonal variation of 19-norcholest-4-en-3-one and 3 beta-monohydroxy sterols in the Californian gorgonian, Muricea californica

Alitta succinea

1 reference

Sex pheromones in marine polychaetes: steroids from ripe Nereis succinea

Neanthes succinea

1 reference

Sex pheromones in marine polychaetes: steroids from ripe Nereis succinea

Kali collinum

1 reference

Sterols ofSalsola collina

Salsola collina

1 reference

Sterols ofSalsola collina

Crassostrea gigas

1 reference

Sterol Metabolism of Pacific Oyster (Crassostrea gigas) Spat

Halopithys incurva

1 reference

Sterols of the amansieae (rhodomelaceae: Rhodophyta)

Halopithys incurvus

1 reference

Sterols of the amansieae (rhodomelaceae: Rhodophyta)

tomato

1 reference

Plant cholesterol biosynthetic pathway overlaps with phytosterol metabolism.

Tethya aurantium

2 references

Biosynthetic studies of marine lipids-xxix. Demonstration of sterol side chain dealkylation using cell-free extracts of marine sponges

Biosynthetic studies of marine lipids. 38. Mechanism and scope of sterol side chain dealkylation in sponges: evidence for concurrent alkylation and dealkylation

house mouse

1 reference

Desmosterol as the Major Sterol in L-Cell Mouse Fibroblasts Grown in Sterol-Free Culture Medium

1 reference

https://reactome.org/PathwayBrowser/#/R-HSA-1430728&DTAB=MT

Commons category

Desmosterol

0 references

Identifiers

InChI

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

1 reference

DESMOSTEROL (English)

AVSXSVCZWQODGV-DPAQBDIFSA-N

3 October 2016

InChIKey

2 references

DESMOSTEROL (English)

3 October 2016

ChEBI release 2020-09-01

2 references

desmosterol (English)

AVSXSVCZWQODGV-DPAQBDIFSA-N

3 October 2016

InChIKey

10 April 2021

https://commonchemistry.cas.org/detail?cas_rn=313-04-2

1 reference

Desmesterol (English)

3 October 2016

1 reference

DESMOSTEROL (English)

3 October 2016

Reaxys registry number

2338693

1 reference

desmosterol (English)

3 October 2016

ChEBI ID

17737

mapping relation type

1 reference

desmosterol (English)

3 October 2016

1 reference

MSBNK-Fac_Eng_Univ_Tokyo-JP009550

DESMOSTEROL (English)

3 October 2016

1 reference

inferred from InChIKey

1 reference

MassBank accession ID

0 references

SPLASH

splash10-0a4s-6913000000-a348d9fdea450ccd7658

0 references

splash10-0avl-7941000000-99b5e69bc97a4056fa8c

0 references

DSSTox substance ID

DTXSID10878676

0 references

DSSTOX compound identifier

0 references

0 references

206-236-2

1 reference

Global Substance Registration System

UNII

ANP93865R8

DESMOSTEROL (English)

ECHA Substance Infocard ID

3 October 2016

100.005.671

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.005.671

27 December 2018

Guide to Pharmacology Ligand ID

Cholesta-5,24-dien-3-β-ol (English)

quotation

CAS no.: 313-04-2 (English)

1 reference

2748

1 reference

IUPHAR/BPS Guide to PHARMACOLOGY

Guide to Pharmacology Ligand ID

2748

D04.210.500.247.222.222.347.231

desmosterol (English)

3 October 2016

Desmosterol

0 references

MeSH tree code

0 references

D04.210.500.247.808.197.250.281

0 references

D10.570.938.208.320.297

0 references

Human Metabolome Database ID

HMDB0002719

1 reference

inferred from InChIKey

1 reference

Global Substance Registration System

desmosterol (English)

3 October 2016

1 reference

UNII

ANP93865R8

https://docs.openalex.org/download-snapshot/snapshot-data-format

DESMOSTEROL (English)

3 October 2016

0 references

0 references

0 references

0 references

Microsoft Academic ID

0 references

1 reference

26 January 2022

UMLS CUI

C0011704

1 reference

inferred by common MeSH mappings on source and on Wikidata

UMLS 2023