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

Details

• Internal ID: fbfd7ced-56c8-4fb0-8363-0f33fce38030
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,3S,4aR,5R,7R,8R,8aS)-3,5,7-triacetyloxy-8-[(2R,3R)-2-acetyloxy-3-hydroxy-3-methylpent-4-enyl]-4,4,7,8a-tetramethyl-2,3,4a,5,6,8-hexahydro-1H-naphthalen-2-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2(C(C(CC(C2C(C1OC(=O)C)(C)C)OC(=O)C)(C)OC(=O)C)CC(C(C)(C=C)O)OC(=O)C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@]2([C@H]([C@](C[C@H]([C@H]2C([C@@H]1OC(=O)C)(C)C)OC(=O)C)(C)OC(=O)C)C[C@H]([C@@](C)(C=C)O)OC(=O)C)C
• InChI: InChI=1S/C30H46O11/c1-12-29(10,36)24(39-18(4)33)13-23-28(9)14-22(38-17(3)32)26(40-19(5)34)27(7,8)25(28)21(37-16(2)31)15-30(23,11)41-20(6)35/h12,21-26,36H,1,13-15H2,2-11H3/t21-,22-,23-,24-,25+,26-,28-,29-,30-/m1/s1
• InChI Key: PJZOYAIOGNEXPK-ZKKRRHGASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₁₁
• Molecular Weight: 582.70 g/mol
• Exact Mass: 582.30401228 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	-	0.7665	76.65%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7407	74.07%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	+	0.9051	90.51%
OATP1B3 inhibitior	+	0.8225	82.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9234	92.34%
P-glycoprotein inhibitior	+	0.7907	79.07%
P-glycoprotein substrate	-	0.5995	59.95%
CYP3A4 substrate	+	0.6721	67.21%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	+	0.5795	57.95%
CYP2C9 inhibition	-	0.8673	86.73%
CYP2C19 inhibition	-	0.8259	82.59%
CYP2D6 inhibition	-	0.9669	96.69%
CYP1A2 inhibition	-	0.8715	87.15%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9653	96.53%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.6560	65.60%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.8826	88.26%
Skin irritation	-	0.6243	62.43%
Skin corrosion	-	0.9574	95.74%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4397	43.97%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6274	62.74%
skin sensitisation	-	0.6465	64.65%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6234	62.34%
Acute Oral Toxicity (c)	III	0.5853	58.53%
Estrogen receptor binding	+	0.7708	77.08%
Androgen receptor binding	+	0.5998	59.98%
Thyroid receptor binding	+	0.5714	57.14%
Glucocorticoid receptor binding	+	0.7615	76.15%
Aromatase binding	+	0.7041	70.41%
PPAR gamma	+	0.7261	72.61%
Honey bee toxicity	-	0.6018	60.18%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	97.34%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.23%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.99%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.34%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.41%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.37%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.88%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.70%	94.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.65%	97.28%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.58%	89.34%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.84%	97.29%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.75%	96.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.60%	89.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.31%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.79%	91.03%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.39%	91.24%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	83.09%	92.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.23%	98.75%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.15%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.01%	99.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.17%	95.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.08%	85.14%
CHEMBL2061	P19793	Retinoid X receptor alpha	80.98%	91.67%

Plants that contains it

• Ptychanthus striatus

Cross-Links

• PubChem: 163005654
• LOTUS: LTS0045015
• wikiData: Q105210252