3-[(1R,2R,6R)-1-methyl-3-methylidene-2-[(2E)-3-methylpenta-2,4-dienyl]-6-prop-1-en-2-ylcyclohexyl]propanoic acid

Details

• Internal ID: 6731b489-86d0-477c-a80e-7ff1085fbac9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 3-[(1R,2R,6R)-1-methyl-3-methylidene-2-[(2E)-3-methylpenta-2,4-dienyl]-6-prop-1-en-2-ylcyclohexyl]propanoic acid
• SMILES (Canonical): CC(=C)C1CCC(=C)C(C1(C)CCC(=O)O)CC=C(C)C=C
• SMILES (Isomeric): CC(=C)[C@H]1CCC(=C)[C@H]([C@]1(C)CCC(=O)O)C/C=C(\C)/C=C
• InChI: InChI=1S/C20H30O2/c1-7-15(4)8-10-18-16(5)9-11-17(14(2)3)20(18,6)13-12-19(21)22/h7-8,17-18H,1-2,5,9-13H2,3-4,6H3,(H,21,22)/b15-8+/t17-,18-,20-/m1/s1
• InChI Key: IOAMLRWLTANBPN-RCIDRGNJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.50 g/mol
• Exact Mass: 302.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.54
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.8114	81.14%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5854	58.54%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8846	88.46%
OATP1B3 inhibitior	+	0.8430	84.30%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6150	61.50%
P-glycoprotein inhibitior	-	0.8101	81.01%
P-glycoprotein substrate	-	0.6633	66.33%
CYP3A4 substrate	+	0.6071	60.71%
CYP2C9 substrate	-	0.5641	56.41%
CYP2D6 substrate	-	0.9040	90.40%
CYP3A4 inhibition	-	0.7540	75.40%
CYP2C9 inhibition	-	0.8665	86.65%
CYP2C19 inhibition	-	0.9152	91.52%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.8286	82.86%
CYP2C8 inhibition	-	0.6289	62.89%
CYP inhibitory promiscuity	-	0.9454	94.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8043	80.43%
Carcinogenicity (trinary)	Non-required	0.6545	65.45%
Eye corrosion	-	0.9619	96.19%
Eye irritation	-	0.8432	84.32%
Skin irritation	+	0.6007	60.07%
Skin corrosion	-	0.9786	97.86%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6707	67.07%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.7906	79.06%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.6200	62.00%
Acute Oral Toxicity (c)	III	0.8678	86.78%
Estrogen receptor binding	-	0.7939	79.39%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6641	66.41%
Aromatase binding	-	0.5883	58.83%
PPAR gamma	+	0.6635	66.35%
Honey bee toxicity	-	0.8745	87.45%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9949	99.49%

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	97.24%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.76%	83.82%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.27%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.56%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	87.91%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.06%	95.56%
CHEMBL5028	O14672	ADAM10	80.74%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.74%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.21%	95.89%

Plants that contains it

• Croton costatus
• Croton matourensis

Cross-Links

• PubChem: 162926216
• LOTUS: LTS0254647
• wikiData: Q105116554