Aconitic acid

Details

• Internal ID: fcebb325-7fe3-44b3-8cbd-835022c57e2e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: prop-1-ene-1,2,3-tricarboxylic acid
• SMILES (Canonical): C(C(=CC(=O)O)C(=O)O)C(=O)O
• SMILES (Isomeric): C(C(=CC(=O)O)C(=O)O)C(=O)O
• InChI: InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)
• InChI Key: GTZCVFVGUGFEME-UHFFFAOYSA-N
• Popularity: 339 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₆O₆
• Molecular Weight: 174.11 g/mol
• Exact Mass: 174.01643791 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.44
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 1-Propene-1,2,3-tricarboxylic acid
• 499-12-7
• Propene-1,2,3-tricarboxylic acid
• NSC7616
• C6-H6-O6
• Spectrum_001377
• DISPERSEVIOLET26
• SpecPlus_000379
• Spectrum2_001788
• Spectrum3_001348
• Spectrum4_001744
• NCIStruc1_000121
• NCIStruc2_000171
• KBioGR_002188
• KBioSS_001857
• DivK1c_006475
• SPBio_001715
• DTXSID9060102
• CHEBI:22211
• KBio1_001419
• KBio2_001857
• KBio2_004425
• KBio2_006993
• KBio3_002355
• GTZCVFVGUGFEME-UHFFFAOYSA-N
• AKOS028109456
• NCI60_041679
• FT-0623933
• FT-0659941
• D78372
• Q288782

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8319	83.19%
Caco-2	-	0.7270	72.70%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7588	75.88%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9482	94.82%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9888	98.88%
P-glycoprotein inhibitior	-	0.9837	98.37%
P-glycoprotein substrate	-	0.9811	98.11%
CYP3A4 substrate	-	0.7582	75.82%
CYP2C9 substrate	-	0.7552	75.52%
CYP2D6 substrate	-	0.8984	89.84%
CYP3A4 inhibition	-	0.9523	95.23%
CYP2C9 inhibition	-	0.9433	94.33%
CYP2C19 inhibition	-	0.9662	96.62%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.9507	95.07%
CYP2C8 inhibition	-	0.9858	98.58%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6135	61.35%
Carcinogenicity (trinary)	Non-required	0.6807	68.07%
Eye corrosion	+	0.7749	77.49%
Eye irritation	+	0.9908	99.08%
Skin irritation	+	0.5000	50.00%
Skin corrosion	+	0.7960	79.60%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8675	86.75%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6053	60.53%
skin sensitisation	+	0.4769	47.69%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.8556	85.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6277	62.77%
Acute Oral Toxicity (c)	III	0.7914	79.14%
Estrogen receptor binding	-	0.9348	93.48%
Androgen receptor binding	-	0.7204	72.04%
Thyroid receptor binding	-	0.9198	91.98%
Glucocorticoid receptor binding	-	0.6765	67.65%
Aromatase binding	-	0.9008	90.08%
PPAR gamma	-	0.7758	77.58%
Honey bee toxicity	-	0.9459	94.59%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8900	89.00%
Fish aquatic toxicity	+	0.7773	77.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	85.12%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	83.21%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.96%	91.11%
CHEMBL1255126	O15151	Protein Mdm4	80.39%	90.20%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.02%	100.00%

Plants that contains it

• Aconitum barbatum
• Adonis vernalis
• Asarum europaeum
• Glochidion zeylanicum
• Helinus integrifolius
• Ribes rubrum
• Zea mays

Cross-Links

• PubChem: 309
• NPASS: NPC115727
• LOTUS: LTS0039736
• wikiData: Q288782