Ketcher 05282121212D 1   1.00000     0.00000     0

 32 36  0     1  0            999 V2000
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   -1.3178    0.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4518    1.6371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4143    1.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7930    1.8062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1463   -2.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2802   -3.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  4  1  0     0  0
  2  5  1  0     0  0
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  3  8  2  0     0  0
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  6 30  1  0     0  0
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  7 13  2  0     0  0
  9 14  1  0     0  0
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 19 21  2  0     0  0
 20 22  1  0     0  0
 21 23  1  0     0  0
 22 24  1  0     0  0
  8 11  1  0     0  0
  9 12  1  0     0  0
 10 30  1  0     0  0
 16 17  1  0     0  0
 20 21  1  0     0  0
  9 25  1  1     0  0
 12 26  1  1     0  0
 30 27  1  0     0  0
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 27 29  2  0     0  0
 30 31  1  6     0  0
 23 32  1  0     0  0
M  END
> <ID>
CHEBI:28201

> <NAME>
rotenone

> <DEFINITION>
A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).

> <STAR>
3

> <SECONDARY_ID>
CHEBI:8897; CHEBI:26583

> <SYNONYM>
tubatoxin; Rotenone; paraderil; noxfire; Derris; dactinol; canex; barbasco; [2R-(2alpha,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6aH)-one; 5'beta-rotenone; (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one; (-)-rotenone; (-)-cis-rotenone

> <IUPAC_NAME>
(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

> <FORMULA>
C23H22O6

> <MASS>
394.423

> <MONOISOTOPIC_MASS>
394.14164

> <CHARGE>
0

> <SMILES>
[H][C@@]1(CC2=C3O[C@]4([H])COC5=C(C=C(OC)C(OC)=C5)[C@]4([H])C(=O)C3=CC=C2O1)C(C)=C

> <INCHI>
InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

> <INCHIKEY>
JUVIOZPCNVVQFO-HBGVWJBISA-N

> <BEILSTEIN_REGISTRY_NUMBER>
99070

> <CAS_REGISTRY_NUMBER>
83-79-4

> <REAXYS_REGISTRY_NUMBER>
99070

> <CHEMIDPLUS>
83-79-4

> <DRUGBANK_ACCESSION>
DB11457

> <KEGG_COMPOUND_ACCESSION>
C07593

> <KNAPSACK_ACCESSION>
C00002568

> <LINCS_ACCESSION>
LSM-5260

> <LIPID_MAPS_INSTANCE_ACCESSION>
LMPK12060007

> <NIST_CHEMISTRY_WEBBOOK>
83-79-4

> <PDBECHEM_ACCESSION>
970

> <WIKIPEDIA_ACCESSION>
Rotenone

> <PUBMED_CITATION>
14976342; 15043430; 15790535; 17077549; 19013527; 32972993; 33402167; 33901458; 33961406

$$$$