2-[(1R,2R,4S,5S)-4-ethenyl-4-methyl-2-[(E)-2-methylbut-2-enoyl]oxy-5-prop-1-en-2-ylcyclohexyl]prop-2-enoic acid

Details

• Internal ID: 5e8ca802-4046-41b8-bf03-a9b88a7e0359
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Elemane sesquiterpenoids
• IUPAC Name: 2-[(1R,2R,4S,5S)-4-ethenyl-4-methyl-2-[(E)-2-methylbut-2-enoyl]oxy-5-prop-1-en-2-ylcyclohexyl]prop-2-enoic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C(CC1C(=C)C(=O)O)C(=C)C)(C)C=C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C[C@@]([C@@H](C[C@@H]1C(=C)C(=O)O)C(=C)C)(C)C=C
• InChI: InChI=1S/C20H28O4/c1-8-13(5)19(23)24-17-11-20(7,9-2)16(12(3)4)10-15(17)14(6)18(21)22/h8-9,15-17H,2-3,6,10-11H2,1,4-5,7H3,(H,21,22)/b13-8+/t15-,16+,17-,20-/m1/s1
• InChI Key: ZYYGYFSSHRZSCL-AGUIXGIGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.30
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9708	97.08%
Caco-2	+	0.6043	60.43%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8554	85.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9246	92.46%
OATP1B3 inhibitior	+	0.9191	91.91%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8200	82.00%
P-glycoprotein inhibitior	-	0.7122	71.22%
P-glycoprotein substrate	-	0.7213	72.13%
CYP3A4 substrate	+	0.6436	64.36%
CYP2C9 substrate	-	0.5701	57.01%
CYP2D6 substrate	-	0.9246	92.46%
CYP3A4 inhibition	-	0.5167	51.67%
CYP2C9 inhibition	-	0.8903	89.03%
CYP2C19 inhibition	-	0.8493	84.93%
CYP2D6 inhibition	-	0.9264	92.64%
CYP1A2 inhibition	-	0.8146	81.46%
CYP2C8 inhibition	-	0.7883	78.83%
CYP inhibitory promiscuity	-	0.9412	94.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7139	71.39%
Carcinogenicity (trinary)	Non-required	0.6217	62.17%
Eye corrosion	-	0.9750	97.50%
Eye irritation	-	0.9033	90.33%
Skin irritation	+	0.5222	52.22%
Skin corrosion	-	0.9705	97.05%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7077	70.77%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5484	54.84%
skin sensitisation	+	0.5574	55.74%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.7764	77.64%
Acute Oral Toxicity (c)	III	0.5905	59.05%
Estrogen receptor binding	+	0.6193	61.93%
Androgen receptor binding	+	0.5659	56.59%
Thyroid receptor binding	+	0.6655	66.55%
Glucocorticoid receptor binding	-	0.5283	52.83%
Aromatase binding	-	0.6010	60.10%
PPAR gamma	+	0.5296	52.96%
Honey bee toxicity	-	0.5000	50.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	+	0.9967	99.67%

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	95.06%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.66%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	92.42%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.85%	96.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.73%	91.11%
CHEMBL284	P27487	Dipeptidyl peptidase IV	89.23%	95.69%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.58%	97.53%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.73%	97.53%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.52%	93.00%

Plants that contains it

• Ageratina tomentella

Cross-Links

• PubChem: 13970436
• LOTUS: LTS0016011
• wikiData: Q105386545