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

Details

• Internal ID: dcca1b9f-90a9-4c4f-917a-64dd9f8fb0cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(1S,2R,4aS,8S,8aR)-8-acetyloxy-5-(3,5-dihydroxy-3-methylpentyl)-2-hydroxy-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate
• SMILES (Canonical): CC1=C(C2(CCC(C(C2C(C1=O)OC(=O)C)(C)COC(=O)C)O)C)CCC(C)(CCO)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)O)C)CCC(C)(CCO)O
• InChI: InChI=1S/C24H38O8/c1-14-17(7-9-22(4,30)11-12-25)23(5)10-8-18(28)24(6,13-31-15(2)26)21(23)20(19(14)29)32-16(3)27/h18,20-21,25,28,30H,7-13H2,1-6H3/t18-,20-,21-,22?,23-,24+/m1/s1
• InChI Key: SGWHOCKDQUUVNF-SDTSKVPRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₈O₈
• Molecular Weight: 454.60 g/mol
• Exact Mass: 454.25666817 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9374	93.74%
Caco-2	+	0.5238	52.38%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8329	83.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8531	85.31%
OATP1B3 inhibitior	+	0.8089	80.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5890	58.90%
BSEP inhibitior	+	0.8260	82.60%
P-glycoprotein inhibitior	-	0.4636	46.36%
P-glycoprotein substrate	-	0.5500	55.00%
CYP3A4 substrate	+	0.6974	69.74%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.9121	91.21%
CYP3A4 inhibition	-	0.8268	82.68%
CYP2C9 inhibition	-	0.8677	86.77%
CYP2C19 inhibition	-	0.8891	88.91%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.5085	50.85%
CYP inhibitory promiscuity	-	0.9424	94.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7207	72.07%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9227	92.27%
Skin irritation	-	0.5216	52.16%
Skin corrosion	-	0.9666	96.66%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5522	55.22%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5467	54.67%
skin sensitisation	-	0.9202	92.02%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6038	60.38%
Acute Oral Toxicity (c)	III	0.6811	68.11%
Estrogen receptor binding	+	0.7592	75.92%
Androgen receptor binding	+	0.6383	63.83%
Thyroid receptor binding	-	0.5463	54.63%
Glucocorticoid receptor binding	+	0.8120	81.20%
Aromatase binding	+	0.6210	62.10%
PPAR gamma	+	0.6634	66.34%
Honey bee toxicity	-	0.7955	79.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9814	98.14%

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	98.14%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.14%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.64%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.78%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.31%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	89.19%	97.79%
CHEMBL3437	Q16853	Amine oxidase, copper containing	89.09%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.05%	94.45%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.38%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.83%	86.33%
CHEMBL5028	O14672	ADAM10	85.16%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.92%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.39%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.02%	94.75%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.91%	94.62%
CHEMBL4040	P28482	MAP kinase ERK2	83.74%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.37%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.61%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.10%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.75%	89.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.37%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	81.27%	91.19%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	81.12%	91.65%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.04%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.09%	92.50%

Plants that contains it

• Leonurus macranthus

Cross-Links

• PubChem: 122187011
• LOTUS: LTS0237570
• wikiData: Q105252671