Ketcher 02252113512D 1   1.00000     0.00000     0

 22 22  0     0  0            999 V2000
   11.8242    0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1355   -0.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3241   -1.4094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5129   -0.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2369    0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034    0.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3975   -0.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8944   -1.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9007    0.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8941   -1.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6370   -1.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7711   -0.8193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6344   -2.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2372    0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7460    1.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  1     0  0
  1  2  1  0     0  0
  7  8  1  0     0  0
  1  7  1  1     0  0
  7  9  2  0     0  0
  2  3  1  0     0  0
  9 10  1  0     0  0
 10 11  2  0     0  0
  3  4  1  0     0  0
 11 12  1  0     0  0
 12 13  1  0     0  0
  4  5  1  0     0  0
 13 14  1  0     0  0
 13 15  2  0     0  0
  5  1  1  0     0  0
 12 16  1  6     0  0
  4 17  1  6     0  0
 17 18  1  0     0  0
 17 19  2  0     0  0
  6 20  1  0     0  0
 20 21  2  0     0  0
 20 22  1  0     0  0
M  END
> <ID>
CHEBI:34727

> <NAME>
domoic acid

> <DEFINITION>
An L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP).

> <STAR>
3

> <SYNONYM>
L-domoic acid

> <IUPAC_NAME>
(3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline

> <FORMULA>
C15H21NO6

> <MASS>
311.334

> <MONOISOTOPIC_MASS>
311.13689

> <CHARGE>
0

> <SMILES>
C[C@H](\C=C\C=C(\C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O)C(O)=O

> <INCHI>
InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1

> <INCHIKEY>
VZFRNCSOCOPNDB-AOKDLOFSSA-N

> <CAS_REGISTRY_NUMBER>
14277-97-5

> <REAXYS_REGISTRY_NUMBER>
5126272

> <CHEMIDPLUS>
14277-97-5

> <DRUGBANK_ACCESSION>
DB02852

> <KEGG_COMPOUND_ACCESSION>
C13732

> <KNAPSACK_ACCESSION>
C00034487

> <PDBECHEM_ACCESSION>
DOQ

> <WIKIPEDIA_ACCESSION>
Domoic_acid

> <PUBMED_CITATION>
10223629; 1264348; 18728725; 20120452; 22406515; 24511141; 24564603; 24638960; 24663110; 28817087; 32302120; 32512724; 32891664; 33153112; 33193520; 33218768; 33347336; 33517972; 33524817; 33530611

$$$$