Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
twitter

MetaCyc Compound: squalene

Summary:
Squalene is a naturally occurring polyprenyl compound primarily known for its key role as an intermediate in sterol biosynthesis. The name originates from the scientific name for the shark (Squalus spp.), since shark liver oil is considered the richest source of squalene.

Chemical Formula: C30H50

Molecular Weight: 410.72 Daltons

Monoisotopic Molecular Weight: 410.391251605 Daltons

SMILES: CC(C)=CCCC(=CCCC(C)=CCCC=C(CCC=C(C)CCC=C(C)C)C)C

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: InChIKey=YYGNTYWPHWGJRM-FZSSMNSJSA-N

Unification Links: CAS:111-02-4 , ChEBI:15440 , HMDB:HMDB00256 , KEGG:C00751 , LIPID MAPS:LMPR0106010002 , MetaboLights:MTBLC15440 , PubChem:25244109

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 675.236 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

botryococcenes and methylated squalene biosynthesis :
squalene + S-adenosyl-L-methionine → 3-methyl-1,2-didehydro-2,3-dihydrosqualene + S-adenosyl-L-homocysteine + H+

dammara-20,24-diene biosynthesis :
squalene → dammara-20,24-dien

diploterol and cycloartenol biosynthesis :
squalene → hop-22(29)-ene
squalene + NADPH + oxygen + H+ → (3S)-2,3-epoxy-2,3-dihydrosqualene + NADP+ + H2O
squalene + H2O → hopan-22-ol

epoxysqualene biosynthesis :
squalene + NADPH + oxygen + H+ → (3S)-2,3-epoxy-2,3-dihydrosqualene + NADP+ + H2O

hopanoid biosynthesis (bacteria) :
tetrahymanol ← squalene + H2O
squalene → hop-22(29)-ene
squalene + H2O → hopan-22-ol

Not in pathways:
squalene + 2 S-adenosyl-L-methionine → 3,22-dimethyl-1,2,23,24-tetradehydro-2,3,22,23-tetrahydrosqualene + 2 S-adenosyl-L-homocysteine + 2 H+

Reactions known to produce the compound:

botryococcenes and methylated squalene biosynthesis :
squalene + NADP+ + diphosphate ← presqualene diphosphate + NADPH + H+

epoxysqualene biosynthesis :
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+squalene + NAD(P)+ + 2 diphosphate

In Reactions of unknown directionality:

Not in pathways:
squalene + NAD(P)+ + diphosphate = presqualene diphosphate + NAD(P)H + H+


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Dec 27, 2014, BIOCYC14A.