desmosterol (Q3024529)

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chemical compound

3beta-cholesta-5,24-dien-3-ol
Cholest-5,24-dien-3beta-ol
Cholesta-5,24-dien-3b-ol
Cholesta-5,24-dien-3-ol
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Language	Label	Description	Also known as
English	desmosterol	chemical compound	3beta-cholesta-5,24-dien-3-ol Cholest-5,24-dien-3beta-ol Cholesta-5,24-dien-3b-ol Cholesta-5,24-dien-3-ol (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Statements

type of chemical entity

0 references

0 references

10,13-dimethyl-17-[(2R)-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

1 reference

based on heuristic

inferred from SMILES

cholesterol biosynthetic process via desmosterol

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

ball-and-stick model

0 references

384.339216 dalton

1 reference

language of work or name

DESMOSTEROL (English)

3 October 2016

stereoisomer of

(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

2 references

based on heuristic

inferred from InChIKey

based on heuristic

inferred from InChI

chemical formula

C₂₇H₄₄O

1 reference

language of work or name

DESMOSTEROL (English)

3 October 2016

canonical SMILES

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

1 reference

language of work or name

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

language of work or name

DESMOSTEROL (English)

3 October 2016

2 references

Recon 2.2: from reconstruction to model of human metabolism

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

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

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

Sterols of some chilean algae

Ceramium pacificum

2 references

Sterols of some red algae

Sterols of some chilean 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

Sterols of some chilean algae

Gossypium hirsutum

1 reference

Free and esterified sterols of cotton buds and anthers

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

Sterols of some chilean algae

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

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)

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

1 reference

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

subject has role

primary metabolite

1 reference

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

Commons category

Desmosterol

0 references

Identifiers

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

language of work or name

DESMOSTEROL (English)

3 October 2016

AVSXSVCZWQODGV-DPAQBDIFSA-N

2 references

language of work or name

DESMOSTEROL (English)

3 October 2016

ChEBI release 2020-09-01

CAS Registry Number

2 references

language of work or name

desmosterol (English)

3 October 2016

AVSXSVCZWQODGV-DPAQBDIFSA-N

CAS Common Chemistry

10 April 2021

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

1 reference

language of work or name

Desmesterol (English)

3 October 2016

2 references

language of work or name

DESMOSTEROL (English)

3 October 2016

matched by identifier from

AVSXSVCZWQODGV-DPAQBDIFSA-N

Reaxys registry number

2338693

1 reference

language of work or name

desmosterol (English)

3 October 2016

mapping relation type

2 references

language of work or name

desmosterol (English)

3 October 2016

matched by identifier from

International Chemical Identifier

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

language of work or name

DESMOSTEROL (English)

3 October 2016

2 references

based on heuristic

inferred from InChIKey

matched by identifier from

AVSXSVCZWQODGV-DPAQBDIFSA-N

UniChem compound ID

1 reference

MassBank accession ID

MSBNK-Fac_Eng_Univ_Tokyo-JP009550

0 references

splash10-0a4s-6913000000-a348d9fdea450ccd7658

0 references

splash10-0avl-7941000000-99b5e69bc97a4056fa8c

0 references

DSSTox substance ID

1 reference

matched by identifier from

AVSXSVCZWQODGV-DPAQBDIFSA-N

DSSTOX compound identifier

DTXCID501016718

0 references

0 references

1 reference

Global Substance Registration System

language of work or name

DESMOSTEROL (English)

3 October 2016

ECHA Substance Infocard ID

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

27 December 2018

Cholesta-5,24-dien-3-β-ol (English)

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

Cannabis Database ID

1 reference

Cannabis Database

Guide to Pharmacology Ligand ID

1 reference

IUPHAR/BPS Guide to PHARMACOLOGY

Guide to Pharmacology Ligand ID

language of work or name

desmosterol (English)

3 October 2016

MeSH descriptor ID

subject named as

Desmosterol

0 references

D04.210.500.247.222.222.347.231

0 references

D04.210.500.247.808.197.250.281

0 references

D10.570.938.208.320.297

0 references

Human Metabolome Database ID

2 references

based on heuristic

inferred from InChIKey

matched by identifier from

AVSXSVCZWQODGV-DPAQBDIFSA-N

1 reference

language of work or name

desmosterol (English)

3 October 2016

2 references

Global Substance Registration System

language of work or name

DESMOSTEROL (English)

3 October 2016

matched by identifier from

AVSXSVCZWQODGV-DPAQBDIFSA-N

Probes And Drugs ID

0 references

0 references

0 references

0 references

Microsoft Academic ID

0 references

1 reference

26 January 2022

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

1 reference

based on heuristic

inferred by common MeSH mappings on source and on Wikidata

24 May 2023

Sitelinks

Wikipedia(8 entries)

Wikibooks(0 entries)

Wikinews(0 entries)

Wikiquote(0 entries)

Wikisource(0 entries)

Wikiversity(0 entries)

Wikivoyage(0 entries)

Wiktionary(0 entries)

Multilingual sites(1 entry)

commonswiki Category:Desmosterol

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