squalene (CHEBI:15440)

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CHEBI:15440 - squalene

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ChEBI Name	squalene

ChEBI ID	CHEBI:15440

Definition	A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:10843, CHEBI:9245, CHEBI:10795, CHEBI:15104, CHEBI:26746

Supplier Information	ZINC000096085195

Download	Molfile XML SDF

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The Resolver thinks Mol

SQL - Ideal conformer

Mrv1927 05282116593D

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Time for openFile(SQL - Ideal conformer

Mrv1927 05282116593D

80 79 0 0 0 0 999 V2000

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-1.7620 0.8340 -1.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

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0.2250 -0.6500 -0.9920 C 0 0 1 0 0 0 0 0 0 0 0 0

1.7310 -0.6820 -0.9750 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3620 -1.3530 -0.0430 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5810 -2.1310 0.9840 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8680 -1.3460 0.0020 C 0 0 1 0 0 0 0 0 0 0 0 0

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10.3100 -1.4540 -1.4220 C 0 0 0 0 0 0 0 0 0 0 0 0

5.7710 2.0750 0.2940 C 0 0 0 0 0 0 0 0 0 0 0 0

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-2.3040 0.3100 -1.7730 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1290 1.3170 -1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1080 1.3000 -0.0840 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1600 -1.1650 -0.1110 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2910 -0.1510 -1.7300 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3420 -3.1180 0.5880 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1780 -2.2380 1.8900 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6580 -1.6000 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2260 -2.3190 0.3400 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9870 0.7100 0.6330 H 0 0 0 0 0 0 0 0 0 0 0 0

6.3880 -1.1630 1.2530 H 0 0 0 0 0 0 0 0 0 0 0 0

8.2970 1.8800 1.3090 H 0 0 0 0 0 0 0 0 0 0 0 0

8.3990 -0.3740 -0.7470 H 0 0 0 0 0 0 0 0 0 0 0 0

8.3920 1.3680 -1.1150 H 0 0 0 0 0 0 0 0 0 0 0 0

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7 9 2 0 0 0 0

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24 25 1 0 0 0 0

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26 27 2 3 0 0 0

27 29 1 0 0 0 0

27 28 1 0 0 0 0

1 31 1 0 0 0 0

1 32 1 0 0 0 0

1 33 1 0 0 0 0

3 34 1 0 0 0 0

3 35 1 0 0 0 0

3 36 1 0 0 0 0

4 37 1 0 0 0 0

5 38 1 0 0 0 0

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10 75 1 0 0 0 0

11 76 1 0 0 0 0

16 77 1 0 0 0 0

20 78 1 0 0 0 0

21 79 1 0 0 0 0

24 80 1 0 0 0 0

M END): 18 ms

reading 80 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

80 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Wikipedia	License
Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as Squalus is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection. Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively.
Read full article at Wikipedia

Formula

C30H50

Net Charge

Average Mass

410.730

Monoisotopic Mass

410.39125

InChI

InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+

InChIKey

YYGNTYWPHWGJRM-AAJYLUCBSA-N

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C

Metabolite of Species	Details
Rubia yunnanensis (IPNI:765385-1)	Found in root (BTO:0001188). Methanolic extract of air dried powdered roots. See: PubMed
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Centella asiatica (NCBI:txid48106)	See: MetaboLights Study
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	squalene (CHEBI:15440) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) squalene (CHEBI:15440) has role human metabolite (CHEBI:77746) squalene (CHEBI:15440) has role mouse metabolite (CHEBI:75771) squalene (CHEBI:15440) has role plant metabolite (CHEBI:76924) squalene (CHEBI:15440) is a triterpene (CHEBI:35191)

Incoming	3,22-dimethyl-1,2,23,24-tetradehydro-2,3,22,23-tetrahydrosqualene (CHEBI:70861) has functional parent squalene (CHEBI:15440) 3-methyl-1,2-didehydro-2,3-dihydrosqualene (CHEBI:70860) has functional parent squalene (CHEBI:15440) (R)-12-hydroxysqualene (CHEBI:88123) has parent hydride squalene (CHEBI:15440) (S)-2,3-epoxysqualene (CHEBI:15441) has parent hydride squalene (CHEBI:15440) 2,3-epoxysqualene (CHEBI:78662) has parent hydride squalene (CHEBI:15440) squalene triterpenoid (CHEBI:26747) has parent hydride squalene (CHEBI:15440) tetrahydroxysqualene (CHEBI:66216) has parent hydride squalene (CHEBI:15440)

IUPAC Name

(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Synonyms	Sources
(all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene	NIST Chemistry WebBook
Spinacene	KEGG COMPOUND
Squalene	KEGG COMPOUND
squalene	UniProt
Supraene	KEGG COMPOUND

Manual Xrefs	Databases
C00003755	KNApSAcK
C00751	KEGG COMPOUND
HMDB0000256	HMDB
LMPR0106010002	LIPID MAPS
SQL	PDBeChem
Squalene	Wikipedia
SQUALENE	MetaCyc
View more database links

Registry Numbers	Types	Sources
111-02-4	CAS Registry Number	KEGG COMPOUND
111-02-4	CAS Registry Number	ChemIDplus
111-02-4	CAS Registry Number	NIST Chemistry WebBook
1728920	Beilstein Registry Number	Beilstein

Citations

Christen M, Marcaida MJ, Lamprakis C, Aeschimann W, Vaithilingam J, Schneider P, Hilbert M, Schneider G, Cascella M, Stocker A (2015)
Structural insights on cholesterol endosynthesis: Binding of squalene and 2,3-oxidosqualene to supernatant protein factor.
Journal of structural biology 190, 261-270 [PubMed:25987292]
[show Abstract]

Kouyama T, Fujii R, Kanada S, Nakanishi T, Chan SK, Murakami M (2014)
Structure of archaerhodopsin-2 at 1.8 Å resolution.
Acta crystallographica. Section D, Biological crystallography 70, 2692-2701 [PubMed:25286853]
[show Abstract]

Borshchevskiy V, Round E, Erofeev I, Weik M, Ishchenko A, Gushchin I, Mishin A, Willbold D, Büldt G, Gordeliy V (2014)
Low-dose X-ray radiation induces structural alterations in proteins.
Acta crystallographica. Section D, Biological crystallography 70, 2675-2685 [PubMed:25286851]
[show Abstract]

de Jong A, Cheng TY, Huang S, Gras S, Birkinshaw RW, Kasmar AG, Van Rhijn I, Peña-Cruz V, Ruan DT, Altman JD, Rossjohn J, Moody DB (2014)
CD1a-autoreactive T cells recognize natural skin oils that function as headless antigens.
Nature immunology 15, 177-185 [PubMed:24362891]
[show Abstract]

Zhang J, Mizuno K, Murata Y, Koide H, Murakami M, Ihara K, Kouyama T (2013)
Crystal structure of deltarhodopsin-3 from Haloterrigena thermotolerans.
Proteins 81, 1585-1592 [PubMed:23625688]
[show Abstract]

Kanter JL, Narayana S, Ho PP, Catz I, Warren KG, Sobel RA, Steinman L, Robinson WH (2006)
Lipid microarrays identify key mediators of autoimmune brain inflammation.
Nature medicine 12, 138-143 [PubMed:16341241]
[show Abstract]

Last Modified

28 May 2021

General Comment
2011-04-06	Squalene is the biochemical precursor to the whole family of steroids. Oxidation (via squalene monooxygenase) of one of the terminal double bonds of squalene yields 2,3-squalene oxide, which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids (Wikipedia).

CHEBI:15440 - squalene

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