Genipinic acid

Details

• Internal ID: 8490986a-0e53-462f-8e46-f8ae381eb389
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Dicarboxylic acids and derivatives
• IUPAC Name: 2-(3-hydroxy-3,4,5,6-tetrahydro-1H-cyclopenta[c]furan-4-yl)-3-methoxy-3-oxopropanoic acid
• SMILES (Canonical): COC(=O)C(C1CCC2=C1C(OC2)O)C(=O)O
• SMILES (Isomeric): COC(=O)C(C1CCC2=C1C(OC2)O)C(=O)O
• InChI: InChI=1S/C11H14O6/c1-16-10(14)8(9(12)13)6-3-2-5-4-17-11(15)7(5)6/h6,8,11,15H,2-4H2,1H3,(H,12,13)
• InChI Key: XNIJPPBKASPAIZ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₆
• Molecular Weight: 242.22 g/mol
• Exact Mass: 242.07903816 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.08
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• CHEBI:172481
• 2-(3-hydroxy-3,4,5,6-tetrahydro-1H-cyclopenta[c]uran-4-yl)-3-methoxy-3-oxopropanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9789	97.89%
Caco-2	-	0.7647	76.47%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7919	79.19%
OATP2B1 inhibitior	-	0.8497	84.97%
OATP1B1 inhibitior	+	0.9471	94.71%
OATP1B3 inhibitior	+	0.9641	96.41%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9457	94.57%
P-glycoprotein inhibitior	-	0.9510	95.10%
P-glycoprotein substrate	-	0.7950	79.50%
CYP3A4 substrate	+	0.5565	55.65%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8576	85.76%
CYP3A4 inhibition	-	0.8856	88.56%
CYP2C9 inhibition	-	0.7717	77.17%
CYP2C19 inhibition	-	0.8101	81.01%
CYP2D6 inhibition	-	0.8733	87.33%
CYP1A2 inhibition	+	0.6178	61.78%
CYP2C8 inhibition	-	0.8855	88.55%
CYP inhibitory promiscuity	-	0.9150	91.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.6060	60.60%
Eye corrosion	-	0.8468	84.68%
Eye irritation	-	0.6811	68.11%
Skin irritation	-	0.7653	76.53%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8017	80.17%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5417	54.17%
skin sensitisation	-	0.8568	85.68%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8245	82.45%
Acute Oral Toxicity (c)	III	0.4678	46.78%
Estrogen receptor binding	+	0.5680	56.80%
Androgen receptor binding	-	0.5834	58.34%
Thyroid receptor binding	-	0.6021	60.21%
Glucocorticoid receptor binding	+	0.6168	61.68%
Aromatase binding	-	0.7855	78.55%
PPAR gamma	-	0.6509	65.09%
Honey bee toxicity	-	0.8608	86.08%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9380	93.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.89%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.38%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.82%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	86.99%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.03%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.86%	99.17%
CHEMBL5028	O14672	ADAM10	83.46%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.89%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.39%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.31%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.13%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.80%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	80.49%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	80.25%	95.93%

Plants that contains it

• Genipa americana

Cross-Links

• PubChem: 12310086
• LOTUS: LTS0131900
• wikiData: Q105331684