ChEBI
  Marvin  09060512422D          

 31 31  0  0  1  0            999 V2000
    6.4786    0.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9081   -0.7603    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
    6.0595   -0.7379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6462   -1.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -1.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3411   -1.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -1.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4280   -1.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6899   -0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9714   -1.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333   -0.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -1.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178   -1.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3743   -1.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0702   -0.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8309   -1.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5268   -0.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874   -1.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9833   -0.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7017   -1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4399   -0.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1582   -1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -1.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491   -1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335    0.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5466    0.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4174    0.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
  3  6  1  6  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 27  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 28 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 29 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 30 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  2  0  0  0  0
 26 25  1  0  0  0  0
 31 25  1  0  0  0  0
M  END
> <ID>
CHEBI:15441

> <NAME>
(S)-2,3-epoxysqualene

> <DEFINITION>
A 2,3-epoxysqualene in which the chiral centre has S configuration. It is converted into lanosterol by lanosterol synthase (EC 5.4.99.7) in a key rate-limiting step in the biosynthesis of chloesterol, steroid hormones, and vitamin D.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:18728; CHEBI:11026; CHEBI:11072; CHEBI:372

> <SYNONYM>
Squalene 2,3-oxide; Squalene 2,3-epoxide; oxidosqualene; 2,3-oxidosqualene; 2,3-epoxisqualene; 2,3-EDSQ; (S)-squalene-2,3-epoxide; (S)-Squalene-2,3-epoxide; (S)-2,3-oxidosqualene; (S)-2,3-epoxysqualene; (S)-2,3-epoxysqualene; (S)-2,3-Epoxysqualene; (S)-2,3-epoxy-2,3-dihydrosqualene; (S)-2,3-dihydro-2,3-epoxysqualene; (3S)-2,3-epoxy-2,3-dihydrosqualene; (3S)-2,3-dihydro-2,3-epoxysqualene

> <IUPAC_NAME>
(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane

> <FORMULA>
C30H50O

> <MASS>
426.71740

> <MONOISOTOPIC_MASS>
426.38617

> <CHARGE>
0

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(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+/t29-/m0/s1

> <INCHIKEY>
QYIMSPSDBYKPPY-RSKUXYSASA-N

> <REAXYS_REGISTRY_NUMBER>
4710524

> <KEGG_COMPOUND_ACCESSION>
C01054

> <KNAPSACK_ACCESSION>
C00007282

> <LIPID_MAPS_INSTANCE_ACCESSION>
LMPR0106010010

> <METACYC_ACCESSION>
EPOXYSQUALENE

> <PDBECHEM_ACCESSION>
2TX

> <PUBMED_CITATION>
19951700; 26058429

$$$$