[5-[(4S,4aR,5S,6R,8aS)-4,6-diacetyloxy-5-(acetyloxymethyl)-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-hydroxy-3-methylpentyl] acetate

Details

• Internal ID: 8a2545f8-c429-4741-8585-c9708d09e0af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [5-[(4S,4aR,5S,6R,8aS)-4,6-diacetyloxy-5-(acetyloxymethyl)-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-hydroxy-3-methylpentyl] acetate
• SMILES (Canonical): CC1=C(C2(CCC(C(C2C(C1=O)OC(=O)C)(C)COC(=O)C)OC(=O)C)C)CCC(C)(CCOC(=O)C)O
• SMILES (Isomeric): CC1=C([C@]2(CC[C@H]([C@]([C@@H]2[C@@H](C1=O)OC(=O)C)(C)COC(=O)C)OC(=O)C)C)CCC(C)(CCOC(=O)C)O
• InChI: InChI=1S/C28H42O10/c1-16-21(9-11-26(6,34)13-14-35-17(2)29)27(7)12-10-22(37-19(4)31)28(8,15-36-18(3)30)25(27)24(23(16)33)38-20(5)32/h22,24-25,34H,9-15H2,1-8H3/t22-,24-,25-,26?,27-,28+/m1/s1
• InChI Key: WZQVRGPPHJPVQI-CQXIVQJKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₁₀
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.27779753 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	-	0.6699	66.99%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8676	86.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8453	84.53%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.6298	62.98%
BSEP inhibitior	+	0.8876	88.76%
P-glycoprotein inhibitior	+	0.7748	77.48%
P-glycoprotein substrate	-	0.6038	60.38%
CYP3A4 substrate	+	0.6905	69.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9177	91.77%
CYP3A4 inhibition	-	0.8419	84.19%
CYP2C9 inhibition	-	0.8921	89.21%
CYP2C19 inhibition	-	0.8847	88.47%
CYP2D6 inhibition	-	0.9552	95.52%
CYP1A2 inhibition	-	0.9239	92.39%
CYP2C8 inhibition	+	0.5756	57.56%
CYP inhibitory promiscuity	-	0.9684	96.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6148	61.48%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8931	89.31%
Skin irritation	-	0.5281	52.81%
Skin corrosion	-	0.9693	96.93%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5196	51.96%
skin sensitisation	-	0.8785	87.85%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5266	52.66%
Acute Oral Toxicity (c)	IV	0.4615	46.15%
Estrogen receptor binding	+	0.7476	74.76%
Androgen receptor binding	+	0.6664	66.64%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7513	75.13%
Aromatase binding	+	0.6487	64.87%
PPAR gamma	+	0.7197	71.97%
Honey bee toxicity	-	0.8207	82.07%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9906	99.06%

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	98.25%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.65%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.27%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	89.64%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.41%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.44%	94.62%
CHEMBL3437	Q16853	Amine oxidase, copper containing	87.22%	94.00%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	86.35%	91.65%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.90%	89.00%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	85.37%	92.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.76%	86.33%
CHEMBL5028	O14672	ADAM10	84.55%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.18%	85.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.75%	93.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.78%	89.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.01%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.95%	97.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.42%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.00%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.92%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.87%	82.69%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.41%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.07%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	80.04%	92.50%

Plants that contains it

• Leonurus macranthus

Cross-Links

• PubChem: 122187009
• LOTUS: LTS0035559
• wikiData: Q105323405