3,7-Didehydrojasmonic acid

Details

• Internal ID: 088e8053-0c0f-4e7a-84b5-9a326da4b449
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones
• IUPAC Name: 2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopenten-1-yl]acetic acid
• SMILES (Canonical): CCC=CCC1=C(CCC1=O)CC(=O)O
• SMILES (Isomeric): CC/C=C\CC1=C(CCC1=O)CC(=O)O
• InChI: InChI=1S/C12H16O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4H,2,5-8H2,1H3,(H,14,15)/b4-3-
• InChI Key: QAAHGFINENUHAR-ARJAWSKDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25 g/mol
• Exact Mass: 208.109944368 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• DTXSID701207183
• 120282-76-0
• 3-Oxo-2-(2Z)-2-penten-1-yl-1-cyclopentene-1-acetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	+	0.6273	62.73%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8619	86.19%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.8647	86.47%
OATP1B3 inhibitior	+	0.9581	95.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8426	84.26%
P-glycoprotein inhibitior	-	0.9817	98.17%
P-glycoprotein substrate	-	0.9308	93.08%
CYP3A4 substrate	-	0.6308	63.08%
CYP2C9 substrate	-	0.7659	76.59%
CYP2D6 substrate	-	0.9025	90.25%
CYP3A4 inhibition	-	0.9034	90.34%
CYP2C9 inhibition	-	0.9124	91.24%
CYP2C19 inhibition	-	0.8879	88.79%
CYP2D6 inhibition	-	0.8943	89.43%
CYP1A2 inhibition	-	0.9269	92.69%
CYP2C8 inhibition	-	0.9395	93.95%
CYP inhibitory promiscuity	-	0.9241	92.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6582	65.82%
Eye corrosion	-	0.9681	96.81%
Eye irritation	+	0.9592	95.92%
Skin irritation	+	0.5371	53.71%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6473	64.73%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.5635	56.35%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7840	78.40%
Acute Oral Toxicity (c)	III	0.7404	74.04%
Estrogen receptor binding	-	0.8614	86.14%
Androgen receptor binding	-	0.7756	77.56%
Thyroid receptor binding	-	0.8361	83.61%
Glucocorticoid receptor binding	-	0.5290	52.90%
Aromatase binding	-	0.7552	75.52%
PPAR gamma	+	0.6908	69.08%
Honey bee toxicity	-	0.9657	96.57%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9358	93.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.15%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.42%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.84%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.22%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	87.19%	89.63%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.54%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.58%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.07%	91.11%

Plants that contains it

• Vicia faba

Cross-Links

• PubChem: 9855819
• LOTUS: LTS0148952
• wikiData: Q105217286