methyl 2-[(1S,2S,3S,4aR,5R,8R,8aS)-3-acetyloxy-1,5,8-trihydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoate

Details

• Internal ID: 5c494f80-9bdf-4bf4-a32b-f0473ea86173
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-[(1S,2S,3S,4aR,5R,8R,8aS)-3-acetyloxy-1,5,8-trihydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC(=O)OC1CC2(C(CCC(C2C(C1C(=C)C(=O)OC)O)(C)O)O)C
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@]2([C@@H](CC[C@@]([C@@H]2[C@H]([C@@H]1C(=C)C(=O)OC)O)(C)O)O)C
• InChI: InChI=1S/C18H28O7/c1-9(16(22)24-5)13-11(25-10(2)19)8-17(3)12(20)6-7-18(4,23)15(17)14(13)21/h11-15,20-21,23H,1,6-8H2,2-5H3/t11-,12+,13+,14-,15+,17-,18+/m0/s1
• InChI Key: OPKIAWIFXOGIIZ-RHZKZCPESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₇
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.18350323 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	-	0.5551	55.51%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7470	74.70%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.9312	93.12%
OATP1B3 inhibitior	-	0.4086	40.86%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7592	75.92%
BSEP inhibitior	-	0.8095	80.95%
P-glycoprotein inhibitior	-	0.7330	73.30%
P-glycoprotein substrate	-	0.7122	71.22%
CYP3A4 substrate	+	0.6946	69.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.6845	68.45%
CYP2C9 inhibition	-	0.7993	79.93%
CYP2C19 inhibition	-	0.8517	85.17%
CYP2D6 inhibition	-	0.9521	95.21%
CYP1A2 inhibition	-	0.7704	77.04%
CYP2C8 inhibition	-	0.7627	76.27%
CYP inhibitory promiscuity	-	0.9551	95.51%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.6766	67.66%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9176	91.76%
Skin irritation	+	0.5202	52.02%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4624	46.24%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.7619	76.19%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7139	71.39%
Acute Oral Toxicity (c)	I	0.4042	40.42%
Estrogen receptor binding	+	0.8200	82.00%
Androgen receptor binding	+	0.5320	53.20%
Thyroid receptor binding	+	0.5952	59.52%
Glucocorticoid receptor binding	+	0.7140	71.40%
Aromatase binding	+	0.5809	58.09%
PPAR gamma	-	0.4908	49.08%
Honey bee toxicity	-	0.6883	68.83%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9951	99.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.97%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.90%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.38%	96.38%
CHEMBL221	P23219	Cyclooxygenase-1	91.34%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	89.35%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.00%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.63%	94.45%
CHEMBL204	P00734	Thrombin	87.92%	96.01%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.65%	94.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.52%	91.03%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.35%	92.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.35%	100.00%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	85.28%	98.99%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.19%	91.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.13%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.62%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.90%	94.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.52%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.73%	91.07%
CHEMBL5028	O14672	ADAM10	81.17%	97.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.16%	95.38%
CHEMBL226	P30542	Adenosine A1 receptor	80.73%	95.93%

Plants that contains it

• Cassinia subtropica

Cross-Links

• PubChem: 14191309
• LOTUS: LTS0004794
• wikiData: Q105196405