[(2R,3S,4S,4aS,4bS,8aS,10aR)-3-acetyloxy-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-4-yl] acetate

Details

• Internal ID: e4c681c4-7655-415a-a2b0-cc8b4db2390e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,3S,4S,4aS,4bS,8aS,10aR)-3-acetyloxy-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1C2C3(CCCC(C3CCC2(CC(C1OC(=O)C)(C)C=C)O)(C)C)C
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]2[C@]3(CCCC([C@@H]3CC[C@]2(C[C@]([C@@H]1OC(=O)C)(C)C=C)O)(C)C)C
• InChI: InChI=1S/C24H38O5/c1-8-22(6)14-24(27)13-10-17-21(4,5)11-9-12-23(17,7)19(24)18(28-15(2)25)20(22)29-16(3)26/h8,17-20,27H,1,9-14H2,2-7H3/t17-,18-,19+,20+,22-,23-,24+/m0/s1
• InChI Key: NBNQZOYMSZEVNS-CZRCWOFFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₈O₅
• Molecular Weight: 406.60 g/mol
• Exact Mass: 406.27192431 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.42
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	+	0.5236	52.36%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8203	82.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.8249	82.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	+	0.8099	80.99%
P-glycoprotein inhibitior	-	0.4322	43.22%
P-glycoprotein substrate	-	0.9043	90.43%
CYP3A4 substrate	+	0.6606	66.06%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	+	0.5313	53.13%
CYP2C9 inhibition	-	0.8529	85.29%
CYP2C19 inhibition	-	0.6332	63.32%
CYP2D6 inhibition	-	0.9685	96.85%
CYP1A2 inhibition	-	0.7173	71.73%
CYP2C8 inhibition	-	0.6769	67.69%
CYP inhibitory promiscuity	-	0.9836	98.36%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6723	67.23%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9202	92.02%
Skin irritation	+	0.6063	60.63%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6946	69.46%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7459	74.59%
skin sensitisation	-	0.7365	73.65%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5129	51.29%
Acute Oral Toxicity (c)	III	0.5386	53.86%
Estrogen receptor binding	+	0.8684	86.84%
Androgen receptor binding	+	0.6021	60.21%
Thyroid receptor binding	+	0.5607	56.07%
Glucocorticoid receptor binding	+	0.7479	74.79%
Aromatase binding	+	0.6519	65.19%
PPAR gamma	+	0.5977	59.77%
Honey bee toxicity	-	0.7549	75.49%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9973	99.73%

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	96.90%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.70%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	92.73%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.16%	93.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.63%	82.69%
CHEMBL2581	P07339	Cathepsin D	87.35%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.47%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.99%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.69%	91.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.09%	91.03%
CHEMBL5255	O00206	Toll-like receptor 4	83.51%	92.50%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	83.24%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.87%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.73%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.45%	91.07%
CHEMBL5028	O14672	ADAM10	82.11%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.11%	93.03%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.92%	95.17%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.83%	95.36%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.40%	94.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.09%	82.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.00%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.42%	94.75%

Plants that contains it

• Ozothamnus diosmifolius

Cross-Links

• PubChem: 163191137
• LOTUS: LTS0253434
• wikiData: Q105176865