2,3-Oxidosqualene

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2,3-Oxidosqualene

IUPAC name 2,2-Dimethyl-3-[(3E,7E,11E,15E)- 3,7,12,16,20-pentamethylhenicosa- 3,7,11,15,19-pentaenyl]oxirane
Other names Squalene oxide 2,3-Squalene oxide
Identifiers
CAS number	7200-26-2
PubChem	5366020
ChemSpider	4517951^Y
MeSH	2,3-oxidosqualene
Jmol-3D images	Image 1 Image 2
SMILES O1C(C)(C)C1CC/C(=C/CC/C(=C/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C)C CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
InChI InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+^Y Key: QYIMSPSDBYKPPY-BANQPHDMSA-N^Y InChI=1/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+ Key: QYIMSPSDBYKPPY-BANQPHDMBU
Properties
Molecular formula	C₃₀H₅₀O
Molar mass	426.717 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,3-(S) Oxidosqualene ((S)-2,3-epoxysqualene) is an intermediate in the synthesis of the membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed from squalene by squalene monooxygenase. 2,3 oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.^[1]

2,3-(R) Oxidosqualene is an inhibitor of lanosterol synthase.

References

^ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Products Reports 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA

Ketone bodies	Acetone · Acetoacetic acid · beta-Hydroxybutyric acid

to DMAPP	Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate · Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate · Phytoene

Non-mevalonate pathway

DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP

To Cholesterol

Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol

Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol

Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol

Steroid

Corticosteroids
(C21 pregnane)

Mineralocorticoids	Pregnenolone · Progesterone · Cortodoxone · Corticosterone · Aldosterone

Glucocorticoids	Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · Cortisol Cortisol · Cortisone

Sex steroids

Androgens (C19 androstane)	DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone DHEA sulfate · Epitestosterone

Estrogens (C18 estrane)	Estrone · Estradiol · Estriol

Nonhuman

Phytosterols	Stigmasterol · Brassicasterol

Ergosterols	Ergosterol · Ergocalciferol

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

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