Kainic acid

Details

• Internal ID: 47b87efa-f933-47cf-adab-14a9a422f3ed
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Amino acids and derivatives > Kainoids
• IUPAC Name: (2S,3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid
• SMILES (Canonical): CC(=C)C1CNC(C1CC(=O)O)C(=O)O
• SMILES (Isomeric): CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
• InChI: InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
• InChI Key: VLSMHEGGTFMBBZ-OOZYFLPDSA-N
• Popularity: 15,103 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.23 g/mol
• Exact Mass: 213.10010796 g/mol
• Topological Polar Surface Area (TPSA): 86.60 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 487-79-6
• Digenin
• Digenic acid
• Helminal
• Kainate
• L-alpha-Kainic acid
• alpha-Kainic acid
• Digensaeure
• Kainsaeure
• Acidum kainicum
• Acide kainique
• Acido kainico
• C10H15NO4
• 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)-
• Kainic acid [INN:JAN]
• alpha- Kainic acid
• Acide kainique [INN-French]
• Acido kainico [INN-Spanish]
• Acidum kainicum [INN-Latin]
• rac Kainic Acid
• (2S,3S,4S)-3-(Carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid
• NSC 136038
• BRN 0086660
• UNII-SIV03811UC
• CHEMBL275040
• SIV03811UC
• DTXSID7040526
• CHEBI:31746
• 2-Carboxy-4-isopropenyl-3-pyrrolidineacetic acid
• 2-Carboxy-3-carboxymethyl-4-isopropenylpyrrolidine
• 3-Pyrrolidineacetic acid, 2-carboxy-4-isopropenyl-
• NSC136038
• NSC-759587
• NCGC00024504-05
• (3S,4R)-3-(carboxymethyl)-4-(prop-1-en-2-yl)-L-proline
• (2S-(2alpha,3beta,4beta))-2-carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid
• 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S-(2alpha,3beta,4beta))-
• 4-22-00-01523 (Beilstein Handbook Reference)
• DTXCID5020526
• (3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-L-proline
• (2S,3S,4S)-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid
• 3-(Carboxymethyl)-4-isopropenylproline
• 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S-(2-alpha,3-beta,4-beta))-
• CAS-487-79-6
• SR-01000075454
• kainic-acid
• NSC-136038
• KAI
• 1p1n
• Kainic acid (synthetic)
• KAINIC ACID [MI]
• Biomol-NT_000217
• KAINIC ACID [INN]
• UPCMLD-DP146
• Lopac0_000656
• SCHEMBL15777
• MLS001074661
• KAINIC ACID [WHO-DD]
• BPBio1_001306
• (-)-(.alpha.)-Kainic Acid
• UPCMLD-DP146:001
• UPCMLD-DP146:002
• HMS2233K05
• HMS3262C13
• HMS3266C11
• HMS3411A21
• HMS3675A21
• HY-N2309
• Tox21_110905
• Tox21_500656
• BDBM50002369
• HB0355
• Kainic Acid - CAS 487-79-6
• AKOS024456995
• Tox21_110905_1
• CCG-204742
• LP00656
• SDCCGSBI-0050635.P002
• NCGC00024504-02
• NCGC00024504-03
• NCGC00024504-04
• NCGC00024504-06
• NCGC00024504-07
• NCGC00024504-08
• NCGC00024504-09
• NCGC00024504-15
• NCGC00261341-01
• SMR000471885
• LS-137114
• CS-0020451
• EU-0100656
• K 0250
• Q390239
• SR-01000597728
• SR-01000075454-1
• SR-01000075454-5
• SR-01000075454-6
• SR-01000075454-7
• SR-01000597728-1
• rel-(3R,4R)-3-(carboxymethyl)-4-isopropenyl-D-proline
• (2S,3S,4S)-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid
• 2S-CARBOXY-4S-(1-METHYLETHENYL)-3S-PYRROLDINEACETIC ACID
• L-proline, 3-(carboxymethyl)-4-(1-methylethenyl)-, (3S,4S)-
• (2S,3S,4S)-3-(Carboxymethyl)-4-Prop-1-En-2-yl-Pyrrolidine-2-Carboxylicacid
• (2S-(2.ALPHA.,3.BETA.,4.BETA.))-2-CARBOXY-4-(1-METHYLETHENYL)-3-PYRROLIDINEACETIC ACID
• 4071-38-9
• InChI=1/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8921	89.21%
Caco-2	-	0.8069	80.69%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6520	65.20%
OATP2B1 inhibitior	-	0.8486	84.86%
OATP1B1 inhibitior	+	0.9383	93.83%
OATP1B3 inhibitior	+	0.9408	94.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9870	98.70%
P-glycoprotein inhibitior	-	0.9767	97.67%
P-glycoprotein substrate	-	0.8020	80.20%
CYP3A4 substrate	-	0.6172	61.72%
CYP2C9 substrate	-	0.5764	57.64%
CYP2D6 substrate	-	0.7857	78.57%
CYP3A4 inhibition	-	0.9849	98.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9238	92.38%
CYP inhibitory promiscuity	-	0.9857	98.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6569	65.69%
Eye corrosion	-	0.9770	97.70%
Eye irritation	+	0.6032	60.32%
Skin irritation	-	0.7439	74.39%
Skin corrosion	-	0.9112	91.12%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7391	73.91%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7626	76.26%
Acute Oral Toxicity (c)	III	0.6145	61.45%
Estrogen receptor binding	-	0.7864	78.64%
Androgen receptor binding	-	0.7802	78.02%
Thyroid receptor binding	-	0.8062	80.62%
Glucocorticoid receptor binding	-	0.6541	65.41%
Aromatase binding	-	0.7698	76.98%
PPAR gamma	-	0.9043	90.43%
Honey bee toxicity	-	0.9402	94.02%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	+	0.9401	94.01%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL256	P0DMS8	Adenosine A3 receptor	77 nM	IC50	PMID: 16250647
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	125.9 nM; 125.9 nM; 125.9 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1918	P39086	Glutamate receptor ionotropic kainate 1	177 nM; 177 nM	Ki; Ki	PMID: 10969973; PMID: 10821708
CHEMBL3683	Q13002	Glutamate receptor ionotropic kainate 2	32 nM; 32.4 nM; 700 nM	Ki; Ki; EC50	PMID: 10821708; PMID: 10969973; via Super-PRED
CHEMBL3684	Q13003	Glutamate receptor ionotropic kainate 3	10 nM; 10 nM	Ki; Ki	PMID: 10821708; PMID: 10969973
CHEMBL2675	Q16478	Glutamate receptor ionotropic kainate 5	177 nM; 80 nM; 8 nM; 177 nM	Ki; Ki; Ki; Ki	via Super-PRED; PMID: 10969973; PMID: 10821708; PMID: 9357531
CHEMBL2009	P42261	Glutamate receptor ionotropic, AMPA 1	7449 nM; 7450 nM	Ki; Ki	PMID: 10821708; PMID: 9357531
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	12200 nM; 12200 nM	Ki; Ki	PMID: 9357531; PMID: 10969973
CHEMBL3190	P48058	Glutamate receptor ionotropic, AMPA 4	1710 nM; 1710 nM	Ki; Ki	PMID: 10969973; PMID: 9357531
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	33600 nM	EC50	PMID: 19819046
CHEMBL1293235	P02545	Prelamin-A/C	631 nM; 5011.9 nM; 631 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	158.5 nM	Potency	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	96.44%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.02%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.58%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.74%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.71%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.22%	94.45%

Plants that contains it

• Abrus melanospermus subsp. melanospermus
• 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: 10255
• NPASS: NPC69374
• ChEMBL: CHEMBL275040
• LOTUS: LTS0017376
• wikiData: Q390239