2-[(1R,3S,4Z)-3-acetyl-4-(carboxymethylidene)-3-methylcyclohexyl]prop-2-enoic acid

Details

• Internal ID: 5b86d961-e7bd-44b2-8aa9-b2cf2af38eca
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: 2-[(1R,3S,4Z)-3-acetyl-4-(carboxymethylidene)-3-methylcyclohexyl]prop-2-enoic acid
• SMILES (Canonical): CC(=O)C1(CC(CCC1=CC(=O)O)C(=C)C(=O)O)C
• SMILES (Isomeric): CC(=O)[C@]\1(C[C@@H](CC/C1=C/C(=O)O)C(=C)C(=O)O)C
• InChI: InChI=1S/C14H18O5/c1-8(13(18)19)10-4-5-11(6-12(16)17)14(3,7-10)9(2)15/h6,10H,1,4-5,7H2,2-3H3,(H,16,17)(H,18,19)/b11-6-/t10-,14-/m1/s1
• InChI Key: GCFUBIUESOFTEI-PHLAARDNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.29 g/mol
• Exact Mass: 266.11542367 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9360	93.60%
Caco-2	+	0.8137	81.37%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8442	84.42%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9050	90.50%
OATP1B3 inhibitior	+	0.8583	85.83%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6841	68.41%
BSEP inhibitior	-	0.8713	87.13%
P-glycoprotein inhibitior	-	0.9451	94.51%
P-glycoprotein substrate	-	0.8675	86.75%
CYP3A4 substrate	+	0.5158	51.58%
CYP2C9 substrate	-	0.7627	76.27%
CYP2D6 substrate	-	0.9143	91.43%
CYP3A4 inhibition	-	0.8576	85.76%
CYP2C9 inhibition	-	0.8961	89.61%
CYP2C19 inhibition	-	0.9315	93.15%
CYP2D6 inhibition	-	0.8938	89.38%
CYP1A2 inhibition	-	0.8118	81.18%
CYP2C8 inhibition	-	0.8418	84.18%
CYP inhibitory promiscuity	-	0.9268	92.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7666	76.66%
Carcinogenicity (trinary)	Non-required	0.6856	68.56%
Eye corrosion	-	0.9751	97.51%
Eye irritation	-	0.6051	60.51%
Skin irritation	+	0.5663	56.63%
Skin corrosion	-	0.9808	98.08%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6336	63.36%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.6965	69.65%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.5497	54.97%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5545	55.45%
Acute Oral Toxicity (c)	III	0.7710	77.10%
Estrogen receptor binding	-	0.5272	52.72%
Androgen receptor binding	-	0.5207	52.07%
Thyroid receptor binding	-	0.6702	67.02%
Glucocorticoid receptor binding	-	0.7104	71.04%
Aromatase binding	-	0.6114	61.14%
PPAR gamma	-	0.7626	76.26%
Honey bee toxicity	-	0.8426	84.26%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.91%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.29%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	86.91%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.61%	95.56%
CHEMBL2061	P19793	Retinoid X receptor alpha	80.96%	91.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.59%	100.00%

Plants that contains it

• Ozothamnus pholidotus

Cross-Links

• PubChem: 163096474
• LOTUS: LTS0191674
• wikiData: Q105006268