3-(6,9a,9b-Trimethyl-7-prop-1-en-2-yl-1,3a,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl)propanoic acid

Details

• Internal ID: bcdafc41-9ad0-4192-aa1e-2ab0799eb7cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 3-(6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,3a,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl)propanoic acid
• SMILES (Canonical): CC(=C)C1CCC2(C(C1(C)CCC(=O)O)CCC3C2(CC=C3)C)C
• SMILES (Isomeric): CC(=C)C1CCC2(C(C1(C)CCC(=O)O)CCC3C2(CC=C3)C)C
• InChI: InChI=1S/C22H34O2/c1-15(2)17-10-14-22(5)18(20(17,3)13-11-19(23)24)9-8-16-7-6-12-21(16,22)4/h6-7,16-18H,1,8-14H2,2-5H3,(H,23,24)
• InChI Key: JHGHHJNAAWXVMF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.255880323 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 5.84
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7655	76.55%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.3804	38.04%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.8653	86.53%
OATP1B3 inhibitior	-	0.2207	22.07%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.4797	47.97%
P-glycoprotein inhibitior	-	0.7561	75.61%
P-glycoprotein substrate	-	0.6094	60.94%
CYP3A4 substrate	+	0.6094	60.94%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8709	87.09%
CYP3A4 inhibition	-	0.7381	73.81%
CYP2C9 inhibition	-	0.8364	83.64%
CYP2C19 inhibition	-	0.8306	83.06%
CYP2D6 inhibition	-	0.9503	95.03%
CYP1A2 inhibition	-	0.8619	86.19%
CYP2C8 inhibition	-	0.6594	65.94%
CYP inhibitory promiscuity	-	0.8887	88.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6171	61.71%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9291	92.91%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9646	96.46%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7046	70.46%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5603	56.03%
skin sensitisation	+	0.6120	61.20%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6186	61.86%
Acute Oral Toxicity (c)	III	0.6631	66.31%
Estrogen receptor binding	+	0.6471	64.71%
Androgen receptor binding	+	0.5596	55.96%
Thyroid receptor binding	+	0.7281	72.81%
Glucocorticoid receptor binding	+	0.8329	83.29%
Aromatase binding	+	0.6672	66.72%
PPAR gamma	+	0.6056	60.56%
Honey bee toxicity	-	0.8358	83.58%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	96.87%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.23%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.58%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.38%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.57%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.74%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.85%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.52%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	80.07%	91.19%

Plants that contains it

• Commiphora kua

Cross-Links

• PubChem: 163037637
• LOTUS: LTS0043751
• wikiData: Q105127952