[(1R,3R,4R,4aR,8aS)-1,3-diacetyloxy-4-[(2R,3S)-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: 53c5e419-199f-42c1-8a09-eb486f6fcb2d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(1R,3R,4R,4aR,8aS)-1,3-diacetyloxy-4-[(2R,3S)-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(C1C(CC(C2CC(C(C)(C=C)O)OC(=O)C)(C)OC(=O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)OC[C@]12CCCC([C@@H]1[C@@H](C[C@@]([C@@H]2C[C@H]([C@](C)(C=C)O)OC(=O)C)(C)OC(=O)C)OC(=O)C)(C)C
• InChI: InChI=1S/C28H44O9/c1-10-26(8,33)23(36-19(4)31)14-22-27(9,37-20(5)32)15-21(35-18(3)30)24-25(6,7)12-11-13-28(22,24)16-34-17(2)29/h10,21-24,33H,1,11-16H2,2-9H3/t21-,22+,23-,24+,26+,27-,28+/m1/s1
• InChI Key: GTMYDTLSRDMOQX-HEZRANEXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄O₉
• Molecular Weight: 524.60 g/mol
• Exact Mass: 524.29853298 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 9
• 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	+	0.9880	98.80%
Caco-2	-	0.6634	66.34%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8544	85.44%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.8918	89.18%
OATP1B3 inhibitior	+	0.8793	87.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6364	63.64%
BSEP inhibitior	+	0.9030	90.30%
P-glycoprotein inhibitior	+	0.7518	75.18%
P-glycoprotein substrate	-	0.5506	55.06%
CYP3A4 substrate	+	0.6955	69.55%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.6168	61.68%
CYP2C9 inhibition	-	0.7698	76.98%
CYP2C19 inhibition	-	0.8312	83.12%
CYP2D6 inhibition	-	0.9687	96.87%
CYP1A2 inhibition	-	0.8386	83.86%
CYP2C8 inhibition	+	0.6094	60.94%
CYP inhibitory promiscuity	-	0.9614	96.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6502	65.02%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.6188	61.88%
Skin corrosion	-	0.9657	96.57%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3786	37.86%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5774	57.74%
skin sensitisation	-	0.8217	82.17%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6960	69.60%
Estrogen receptor binding	+	0.8276	82.76%
Androgen receptor binding	+	0.6185	61.85%
Thyroid receptor binding	+	0.5812	58.12%
Glucocorticoid receptor binding	+	0.7616	76.16%
Aromatase binding	+	0.7608	76.08%
PPAR gamma	+	0.6671	66.71%
Honey bee toxicity	-	0.6492	64.92%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	99.59%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.00%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.31%	94.62%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	91.08%	92.95%
CHEMBL2581	P07339	Cathepsin D	90.41%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.42%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.57%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.92%	86.33%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.19%	97.29%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.06%	97.28%
CHEMBL340	P08684	Cytochrome P450 3A4	85.59%	91.19%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.23%	91.03%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.21%	98.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.93%	94.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.68%	89.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.31%	95.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.27%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.89%	89.34%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.17%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.12%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.79%	96.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.09%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.06%	94.75%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.83%	95.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.62%	94.08%
CHEMBL5028	O14672	ADAM10	81.38%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.16%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.41%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.39%	100.00%

Plants that contains it

• Ptychanthus striatus

Cross-Links

• PubChem: 15213238
• LOTUS: LTS0267948
• wikiData: Q105019063