Domoic Acid

Details

• Internal ID: cba4af97-7a1f-4065-be36-ff6880443685
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Amino acids and derivatives > Kainoids
• IUPAC Name: (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• SMILES (Canonical): CC(C=CC=C(C)C1CNC(C1CC(=O)O)C(=O)O)C(=O)O
• SMILES (Isomeric): 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
• InChI Key: VZFRNCSOCOPNDB-AOKDLOFSSA-N
• Popularity: 1,689 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁NO₆
• Molecular Weight: 311.33 g/mol
• Exact Mass: 311.13688739 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 14277-97-5
• L-Domoic acid
• NSC 288031
• CHEBI:34727
• (-)-domoic acid
• M02525818H
• DTXSID20274180
• NSC-288031
• (3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline
• (2S,3S,4S)-3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methyl-hexa-1,3-dienyl]pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• 3-Pyrrolidineacetic acid, 2-carboxy-4-((1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl)-, (2S,3S,4S)-
• (3S,4S)-4-((2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)-L-proline
• (2S,3S,4S)-3-(carboxymethyl)-4-((1Z,3E,5R)-5-carboxy-1-methyl-hexa-1,3-dienyl)pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-((2Z,4E,6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-((2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• RefChem:135605
• DTXCID60196579
• 3-pyrrolidineacetic acid, 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-, (2S-(2 alpha,3 beta,4 beta(1E,3E,5R*)))-
• 4-(6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-((2E,4E,6S)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-((2Z,4E)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-((2Z,4E,6S)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• 4-((2E,4Z)-6-carboxy-6-methylhexa-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• HSDB 7242
• Domoic Acid, Mytilus edulis
• BRN 5768789
• MFCD06795841
• (2S,3S,4S)-4-((R,2Z,4E)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• 25-[2alpha, 3beta, 4beta (1Z, 3E, 5R)]-2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic Acid
• (2S,3S,4S)-2-CARBOXY-4-[(1Z,3E,5R)-5-CARBOXY-1-METHYL-1,3-HEXADIENYL]-3-PYRROLIDINEACETIC ACID
• UNII-M02525818H
• AC1NQZQG
• DOMOIC ACID [MI]
• DOMOIC ACID [HSDB]
• MLS000517259
• Domoic Acid solution in water
• SCHEMBL387531
• GTPL4181
• orb1987381
• CHEMBL1232313
• MSK9117
• Domoic acid, >=90% (HPLC)
• HMS2268I07
• HMS3266E11
• 3-PYRROLIDINEACETIC ACID, 2-CARBOXY-4-((1Z,3E,5R)-5-CARBOXY-1-METHYL-1,3-HEXADIEN-1-YL)-, (2S,3S,4S)-
• HY-N2310
• EX-A14981
• AKOS024457240
• AT27001
• CCG-208195
• DB02852
• NCGC00024520-02
• 3-Pyrrolidineacetic acid, 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-, (2S-(2-alpha,3-beta,4-beta(1Z,3E,5S*)))-
• DA-72879
• FD168217
• SMR000127427
• CS-0020465
• M02718
• Q424386
• SR-01000597723
• SR-01000597723-1
• BRD-K52217427-001-02-3
• (2S,3S,4S)-3-(carboxymethyl)-4-[(2Z,4E,6R)-7-hydroxy-6-methyl-7-oxohepta-2,4-dien-2-yl]pyrrolidine-2-carboxylic acid
• (2S,3S,4S)-4-((R,2Z,4E)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylicacid
• (2S-(2.ALPHA.,3.BETA.,4.BETA.(1Z,3E,5R)))-2-CARBOXY-4-(5-CARBOXY-1-METHYL-1,3-HEXADIENYL)-3-PYRROLIDINEACETIC ACID
• (3S,4S)-3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methylhexa-1,3-dien-1-yl]-L-proline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9086	90.86%
Caco-2	-	0.7579	75.79%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7092	70.92%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8838	88.38%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8250	82.50%
P-glycoprotein inhibitior	-	0.9538	95.38%
P-glycoprotein substrate	-	0.6901	69.01%
CYP3A4 substrate	-	0.5201	52.01%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.8117	81.17%
CYP3A4 inhibition	-	0.9855	98.55%
CYP2C9 inhibition	-	0.9130	91.30%
CYP2C19 inhibition	-	0.9180	91.80%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8818	88.18%
CYP inhibitory promiscuity	-	0.9836	98.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6527	65.27%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.9819	98.19%
Skin irritation	-	0.7646	76.46%
Skin corrosion	-	0.9238	92.38%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6492	64.92%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8557	85.57%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5188	51.88%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8828	88.28%
Acute Oral Toxicity (c)	III	0.6011	60.11%
Estrogen receptor binding	-	0.7344	73.44%
Androgen receptor binding	-	0.7010	70.10%
Thyroid receptor binding	-	0.6579	65.79%
Glucocorticoid receptor binding	-	0.5924	59.24%
Aromatase binding	-	0.5618	56.18%
PPAR gamma	-	0.6929	69.29%
Honey bee toxicity	-	0.8874	88.74%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	+	0.8982	89.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	891.3 nM; 891.3 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.09%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.74%	94.45%
CHEMBL4072	P07858	Cathepsin B	88.97%	93.67%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.18%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.39%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.29%	89.34%
CHEMBL268	P43235	Cathepsin K	84.84%	96.85%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.76%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.25%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.01%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.79%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.38%	91.11%

Plants that contains it

• Anacyclus monanthos
• Arum palaestinum
• Astragalus siculus
• Caulophyllum robustum
• Corydalis balansae
• Euphorbia cuneata
• Guizotia scabra
• Hakea trifurcata
• Mikania cordifolia
• Prunus speciosa
• Raoulia australis
• Senecio chionophilus
• Terminalia brachystemma
• Ulmus glabra

Cross-Links

• PubChem: 5282253
• NPASS: NPC40663
• ChEMBL: CHEMBL1232313