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Domoic Acid

CAT: 1596-AR-D02138-02Size: 25 UnitsDry Ice: NoHazardous: No
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CAS Number
14277-97-5
Synonyms
(2S,3S,4S) -4- ((R,2Z,4E) -6-carboxyhepta-2,4-dien-2-yl) -3- (carboxymethyl) pyrrolidine-2-carboxylic acid; (2S,3S,4S) -2-Carboxy-4-[ (1Z,3E,5R) -5-carboxy-1-methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic Acid; (-) -Domoic Acid; L-Domoic Acid; NSC 288031; DA
Molecular Formula
C15H21NO6
Molecular Weight
311.34
API Name
Domoic Acid

Chemical Information

Domoic Acid

Domoic acid is 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). It has a role as a neurotoxin, a neuromuscular agent, a hapten, a marine metabolite and an algal metabolite. It is a tricarboxylic acid, a pyrrolidinecarboxylic acid, a non-proteinogenic L-alpha-amino acid and a L-proline derivative. It is a conjugate acid of a domoate(2-).

CAS Number14277-97-5
PubChem CID5282253
IUPAC Name(2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
Molecular FormulaC15H21NO6
Molecular Weight311.33
XLogP-1.3
Topological Polar Surface Area124
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Heavy Atom Count22
Formal Charge0
Complexity510
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
Chemical Structure
2D Structure
2D structure of Domoic Acid
CAS: 14277-97-5
CID: 5282253
Formula: C15H21NO6
MW: 311.33
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight311.33
XLogP3-1.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass311.13688739
Monoisotopic Mass311.13688739
Topological Polar Surface Area124 Ų
Heavy Atom Count22
Formal Charge0
Complexity510
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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