[(3R,4R,4aR,8aS)-3-acetyloxy-4-[(2R,3R)-2-acetyloxy-3-hydroxy-3-methylpent-4-enyl]-3,8,8-trimethyl-2,4,5,6,7,8a-hexahydro-1H-naphthalen-4a-yl]methyl acetate

Details

• Internal ID: ad0ccb5e-bd0b-4ecc-b236-ec00b4945299
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(3R,4R,4aR,8aS)-3-acetyloxy-4-[(2R,3R)-2-acetyloxy-3-hydroxy-3-methylpent-4-enyl]-3,8,8-trimethyl-2,4,5,6,7,8a-hexahydro-1H-naphthalen-4a-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC12CCCC(C1CCC(C2CC(C(C)(C=C)O)OC(=O)C)(C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)OC[C@]12CCCC([C@@H]1CC[C@@]([C@@H]2C[C@H]([C@@](C)(C=C)O)OC(=O)C)(C)OC(=O)C)(C)C
• InChI: InChI=1S/C26H42O7/c1-9-24(7,30)22(32-18(3)28)15-21-25(8,33-19(4)29)14-11-20-23(5,6)12-10-13-26(20,21)16-31-17(2)27/h9,20-22,30H,1,10-16H2,2-8H3/t20-,21-,22+,24+,25+,26+/m0/s1
• InChI Key: DAHUQEGQJYTVCS-ROINRSQVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₂O₇
• Molecular Weight: 466.60 g/mol
• Exact Mass: 466.29305367 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.35
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	-	0.5306	53.06%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8849	88.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8983	89.83%
OATP1B3 inhibitior	+	0.9020	90.20%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6114	61.14%
BSEP inhibitior	+	0.7206	72.06%
P-glycoprotein inhibitior	+	0.6851	68.51%
P-glycoprotein substrate	-	0.6771	67.71%
CYP3A4 substrate	+	0.6772	67.72%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.5157	51.57%
CYP2C9 inhibition	-	0.8221	82.21%
CYP2C19 inhibition	-	0.8766	87.66%
CYP2D6 inhibition	-	0.9618	96.18%
CYP1A2 inhibition	-	0.9021	90.21%
CYP2C8 inhibition	+	0.6532	65.32%
CYP inhibitory promiscuity	-	0.9508	95.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6855	68.55%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9209	92.09%
Skin irritation	-	0.6433	64.33%
Skin corrosion	-	0.9707	97.07%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6590	65.90%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5524	55.24%
skin sensitisation	-	0.7893	78.93%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.5648	56.48%
Acute Oral Toxicity (c)	III	0.7189	71.89%
Estrogen receptor binding	+	0.8078	80.78%
Androgen receptor binding	-	0.4827	48.27%
Thyroid receptor binding	+	0.5982	59.82%
Glucocorticoid receptor binding	+	0.7856	78.56%
Aromatase binding	+	0.7333	73.33%
PPAR gamma	+	0.6703	67.03%
Honey bee toxicity	-	0.7089	70.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.86%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.26%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.24%	82.69%
CHEMBL2581	P07339	Cathepsin D	90.83%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.78%	89.34%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.08%	91.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.07%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	86.26%	94.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.08%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.33%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.42%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.29%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.15%	97.09%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	83.84%	92.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.48%	91.24%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.43%	95.71%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.43%	98.75%
CHEMBL5028	O14672	ADAM10	83.39%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.38%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.16%	95.89%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.67%	97.29%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.65%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.55%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.48%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.47%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.43%	100.00%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.16%	86.67%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.84%	93.56%

Plants that contains it

• Ptychanthus striatus

Cross-Links

• PubChem: 162992105
• LOTUS: LTS0026213
• wikiData: Q104973571