Dihydrojasmonic acid

Details

• Internal ID: c471791f-13bc-4c6c-95b6-86b52a4a00d1
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives > Jasmonic acids
• IUPAC Name: 2-(3-oxo-2-pentylcyclopentyl)acetic acid
• SMILES (Canonical): CCCCCC1C(CCC1=O)CC(=O)O
• SMILES (Isomeric): CCCCCC1C(CCC1=O)CC(=O)O
• InChI: InChI=1S/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)
• InChI Key: PQEYTAGBXNEUQL-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.28 g/mol
• Exact Mass: 212.14124450 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 3572-64-3
• (+/-)-Dihydrojasmonic Acid
• 2-(3-oxo-2-pentylcyclopentyl)acetic acid
• 3-Oxo-2-pentylcyclopentaneacetic acid
• Cyclopentaneacetic acid, 3-oxo-2-pentyl-
• 2-Amyl-3-oxocyclopentaneacetic Acid
• 2-Amyl-3-(carboxymethyl)cyclopentanone
• EINECS 222-687-8
• SpecPlus_000429
• Spectrum2_001650
• Spectrum3_001615
• Spectrum4_001665
• Spectrum5_000569
• BSPBio_003249
• KBioGR_002189
• Cyclopentaneacetic acid, 3-oxo-2-pentyl-, (1R,2R)- (9CI)
• DivK1c_006525
• SCHEMBL216000
• SPECTRUM1504104
• SPBio_001779
• CHEMBL3039153
• KBio1_001469
• KBio3_002469
• DTXSID30883989
• CHEBI:177664
• PQEYTAGBXNEUQL-UHFFFAOYSA-N
• CCG-38766
• MFCD08276352
• MFCD18781916
• 2-pentyl-3-oxo-cyclopentylacetic acid
• AKOS037645758
• 3-oxo-2-pentyl-cyclopentaneacetic acid
• SDCCGMLS-0066883.P001
• 3-(Carboxymethyl)-2-pentylcyclopentanone
• NCGC00095830-01
• NCGC00095830-02
• AS-63120
• HY-131116
• CS-0128623
• D3225
• 2-(3-oxo-2-(pentanyl)cyclopentyl)acetic acid
• SR-05000002455
• 3-Oxo-2-pentyl-(1R-trans)-Cyclopentaneacetic acid
• SR-05000002455-1
• W-109908

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	+	0.6378	63.78%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8185	81.85%
OATP2B1 inhibitior	-	0.8424	84.24%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8921	89.21%
P-glycoprotein inhibitior	-	0.9753	97.53%
P-glycoprotein substrate	-	0.7769	77.69%
CYP3A4 substrate	-	0.6014	60.14%
CYP2C9 substrate	+	0.6594	65.94%
CYP2D6 substrate	-	0.8782	87.82%
CYP3A4 inhibition	-	0.9287	92.87%
CYP2C9 inhibition	-	0.9383	93.83%
CYP2C19 inhibition	-	0.9406	94.06%
CYP2D6 inhibition	-	0.9252	92.52%
CYP1A2 inhibition	-	0.9120	91.20%
CYP2C8 inhibition	-	0.9253	92.53%
CYP inhibitory promiscuity	-	0.9803	98.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7492	74.92%
Eye corrosion	-	0.9622	96.22%
Eye irritation	+	0.7960	79.60%
Skin irritation	+	0.7074	70.74%
Skin corrosion	-	0.6185	61.85%
Ames mutagenesis	-	0.8337	83.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.8149	81.49%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.6437	64.37%
skin sensitisation	-	0.7515	75.15%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5609	56.09%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6555	65.55%
Acute Oral Toxicity (c)	III	0.7587	75.87%
Estrogen receptor binding	-	0.8543	85.43%
Androgen receptor binding	+	0.6132	61.32%
Thyroid receptor binding	-	0.8196	81.96%
Glucocorticoid receptor binding	-	0.6771	67.71%
Aromatase binding	-	0.8561	85.61%
PPAR gamma	-	0.7501	75.01%
Honey bee toxicity	-	0.9939	99.39%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5090	50.90%
Fish aquatic toxicity	+	0.9583	95.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.34%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.04%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.99%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.60%	97.25%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	88.07%	90.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.31%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.70%	91.11%
CHEMBL5255	O00206	Toll-like receptor 4	83.56%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.34%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.47%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.25%	99.23%

Plants that contains it

• Vicia faba

Cross-Links

• PubChem: 107126
• LOTUS: LTS0051926
• wikiData: Q82862759