[(1S,2R,4aR,8aR)-1-hydroxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (3S)-3-methylpentanoate

Details

• Internal ID: bcc394cc-614c-4ede-9263-4fb32a09ccaa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2R,4aR,8aR)-1-hydroxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (3S)-3-methylpentanoate
• SMILES (Canonical): CCC(C)CC(=O)OC1CCC2(CC(=O)C(=C(C)C)CC2C1(C)O)C
• SMILES (Isomeric): CC[C@H](C)CC(=O)O[C@@H]1CC[C@@]2(CC(=O)C(=C(C)C)C[C@H]2[C@]1(C)O)C
• InChI: InChI=1S/C21H34O4/c1-7-14(4)10-19(23)25-18-8-9-20(5)12-16(22)15(13(2)3)11-17(20)21(18,6)24/h14,17-18,24H,7-12H2,1-6H3/t14-,17+,18+,20+,21-/m0/s1
• InChI Key: RMKKXWRBWHJNRR-RUXLODGWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.50 g/mol
• Exact Mass: 350.24570956 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 4
• 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	+	0.9936	99.36%
Caco-2	+	0.8222	82.22%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8553	85.53%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8919	89.19%
OATP1B3 inhibitior	+	0.8195	81.95%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6739	67.39%
P-glycoprotein inhibitior	-	0.5835	58.35%
P-glycoprotein substrate	-	0.6722	67.22%
CYP3A4 substrate	+	0.6552	65.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9177	91.77%
CYP3A4 inhibition	-	0.5318	53.18%
CYP2C9 inhibition	-	0.8397	83.97%
CYP2C19 inhibition	-	0.8031	80.31%
CYP2D6 inhibition	-	0.9147	91.47%
CYP1A2 inhibition	-	0.8941	89.41%
CYP2C8 inhibition	-	0.8674	86.74%
CYP inhibitory promiscuity	-	0.8012	80.12%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6808	68.08%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8132	81.32%
Skin irritation	+	0.5329	53.29%
Skin corrosion	-	0.9685	96.85%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6151	61.51%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.6418	64.18%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9281	92.81%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5151	51.51%
Acute Oral Toxicity (c)	III	0.5672	56.72%
Estrogen receptor binding	+	0.7999	79.99%
Androgen receptor binding	-	0.4817	48.17%
Thyroid receptor binding	+	0.6746	67.46%
Glucocorticoid receptor binding	+	0.6913	69.13%
Aromatase binding	-	0.5516	55.16%
PPAR gamma	+	0.6987	69.87%
Honey bee toxicity	-	0.8705	87.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5050	50.50%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.23%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.86%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.87%	94.45%
CHEMBL299	P17252	Protein kinase C alpha	95.58%	98.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.55%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.48%	96.77%
CHEMBL2996	Q05655	Protein kinase C delta	91.32%	97.79%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.76%	85.30%
CHEMBL340	P08684	Cytochrome P450 3A4	87.26%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.99%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.64%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.93%	97.21%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	85.93%	80.96%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.63%	90.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.95%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.57%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.29%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.25%	96.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.19%	89.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.46%	93.04%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.19%	95.71%
CHEMBL1937	Q92769	Histone deacetylase 2	80.86%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.64%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.56%	89.00%

Plants that contains it

• Tessaria integrifolia

Cross-Links

• PubChem: 163050845
• LOTUS: LTS0051541
• wikiData: Q105240846