2-[(1R,2R,3S,4R)-2-formyl-4-methyl-3-(3-oxobutyl)cyclohexyl]prop-2-enoic Acid

Details

• Internal ID: 658624b0-e7cb-4c53-993c-db567b7af119
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: 2-[(1R,2R,3S,4R)-2-formyl-4-methyl-3-(3-oxobutyl)cyclohexyl]prop-2-enoic acid
• InChI: InChI=1S/C15H22O4/c1-9-4-6-13(11(3)15(18)19)14(8-16)12(9)7-5-10(2)17/h8-9,12-14H,3-7H2,1-2H3,(H,18,19)/t9-,12+,13+,14-/m1/s1
• InChI Key: ZUVZYHLJLPPRFY-IGJVIKARSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 4,5-Dioxo-4,5-seco-11(13)-cadinen-12-oic acid
• 2-[(1R,2R,3S,4R)-2-formyl-4-methyl-3-(3-oxobutyl)cyclohexyl]prop-2-enoic Acid
• orb1990913
• AKOS032962411
• 2-((1R,2R,3S,4R)-2-Formyl-4-methyl-3-(3-oxobutyl)cyclohexyl)acrylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9503	95.03%
Caco-2	+	0.7476	74.76%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8478	84.78%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8928	89.28%
OATP1B3 inhibitior	+	0.9069	90.69%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9036	90.36%
P-glycoprotein inhibitior	-	0.9428	94.28%
P-glycoprotein substrate	-	0.7489	74.89%
CYP3A4 substrate	+	0.5153	51.53%
CYP2C9 substrate	+	0.6200	62.00%
CYP2D6 substrate	-	0.8899	88.99%
CYP3A4 inhibition	-	0.7051	70.51%
CYP2C9 inhibition	-	0.9334	93.34%
CYP2C19 inhibition	-	0.9317	93.17%
CYP2D6 inhibition	-	0.8803	88.03%
CYP1A2 inhibition	-	0.8182	81.82%
CYP2C8 inhibition	-	0.7763	77.63%
CYP inhibitory promiscuity	-	0.9090	90.90%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8066	80.66%
Carcinogenicity (trinary)	Non-required	0.7303	73.03%
Eye corrosion	-	0.9555	95.55%
Eye irritation	-	0.6621	66.21%
Skin irritation	-	0.5278	52.78%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5777	57.77%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6608	66.08%
skin sensitisation	+	0.5499	54.99%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.6275	62.75%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.4761	47.61%
Acute Oral Toxicity (c)	III	0.7938	79.38%
Estrogen receptor binding	-	0.8278	82.78%
Androgen receptor binding	-	0.5903	59.03%
Thyroid receptor binding	-	0.7120	71.20%
Glucocorticoid receptor binding	-	0.6128	61.28%
Aromatase binding	-	0.7823	78.23%
PPAR gamma	-	0.6547	65.47%
Honey bee toxicity	-	0.8921	89.21%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.85%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.19%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	87.47%	91.49%
CHEMBL2581	P07339	Cathepsin D	84.52%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.17%	96.38%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.51%	93.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.92%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.03%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.90%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.53%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.10%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.07%	97.09%

Plants that contains it

• Artemisia annua

Cross-Links

• PubChem: 11777696
• LOTUS: LTS0014968
• wikiData: Q105384146