methyl 3-[(1S,4R,5R,8S,9S,11S,12S,13R)-11-acetyloxy-5-[(2R,5R)-5-acetyloxy-6-methylhept-6-en-2-yl]-12-ethenyl-4,8-dimethyl-13-tetracyclo[7.5.0.01,13.04,8]tetradecanyl]propanoate

Details

• Internal ID: ed7b0dce-b484-424b-9ba6-5323637156d6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl 3-[(1S,4R,5R,8S,9S,11S,12S,13R)-11-acetyloxy-5-[(2R,5R)-5-acetyloxy-6-methylhept-6-en-2-yl]-12-ethenyl-4,8-dimethyl-13-tetracyclo[7.5.0.01,13.04,8]tetradecanyl]propanoate
• SMILES (Canonical): CC(CCC(C(=C)C)OC(=O)C)C1CCC2(C1(CCC34C2CC(C(C3(C4)CCC(=O)OC)C=C)OC(=O)C)C)C
• SMILES (Isomeric): C[C@H](CC[C@H](C(=C)C)OC(=O)C)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2C[C@@H]([C@H]([C@]3(C4)CCC(=O)OC)C=C)OC(=O)C)C)C
• InChI: InChI=1S/C34H52O6/c1-10-25-28(40-24(6)36)19-29-32(8)15-13-26(22(4)11-12-27(21(2)3)39-23(5)35)31(32,7)17-18-34(29)20-33(25,34)16-14-30(37)38-9/h10,22,25-29H,1-2,11-20H2,3-9H3/t22-,25-,26-,27-,28+,29+,31-,32+,33-,34+/m1/s1
• InChI Key: NBSDIICNVAGOPK-IHOYDZKNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₂O₆
• Molecular Weight: 556.80 g/mol
• Exact Mass: 556.37638937 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 8.20
• Atomic LogP (AlogP): 7.21
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	-	0.7643	76.43%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7088	70.88%
OATP2B1 inhibitior	-	0.7121	71.21%
OATP1B1 inhibitior	+	0.8254	82.54%
OATP1B3 inhibitior	+	0.8750	87.50%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9463	94.63%
P-glycoprotein inhibitior	+	0.7555	75.55%
P-glycoprotein substrate	+	0.6710	67.10%
CYP3A4 substrate	+	0.7176	71.76%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.6759	67.59%
CYP2C9 inhibition	-	0.7919	79.19%
CYP2C19 inhibition	-	0.8248	82.48%
CYP2D6 inhibition	-	0.9569	95.69%
CYP1A2 inhibition	-	0.8428	84.28%
CYP2C8 inhibition	+	0.6238	62.38%
CYP inhibitory promiscuity	-	0.8055	80.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9520	95.20%
Carcinogenicity (trinary)	Non-required	0.6724	67.24%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.5705	57.05%
Skin corrosion	-	0.9659	96.59%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4573	45.73%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6058	60.58%
skin sensitisation	-	0.7513	75.13%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8023	80.23%
Acute Oral Toxicity (c)	III	0.7168	71.68%
Estrogen receptor binding	+	0.7045	70.45%
Androgen receptor binding	+	0.7267	72.67%
Thyroid receptor binding	-	0.5416	54.16%
Glucocorticoid receptor binding	+	0.7175	71.75%
Aromatase binding	+	0.7123	71.23%
PPAR gamma	+	0.6513	65.13%
Honey bee toxicity	-	0.5074	50.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
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
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	99.14%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.32%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.92%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.81%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	94.19%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	92.54%	97.79%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.86%	95.71%
CHEMBL240	Q12809	HERG	90.93%	89.76%
CHEMBL221	P23219	Cyclooxygenase-1	90.46%	90.17%
CHEMBL3437	Q16853	Amine oxidase, copper containing	90.43%	94.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.62%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.56%	91.07%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.71%	91.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.19%	94.33%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.13%	95.58%
CHEMBL3837	P07711	Cathepsin L	86.65%	96.61%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.56%	89.50%
CHEMBL2581	P07339	Cathepsin D	86.20%	98.95%
CHEMBL233	P35372	Mu opioid receptor	84.14%	97.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.09%	91.24%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.60%	93.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.55%	95.36%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.21%	82.69%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.10%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.05%	89.34%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.00%	92.62%
CHEMBL321	P14780	Matrix metalloproteinase 9	82.74%	92.12%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	82.33%	99.17%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.54%	80.96%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.35%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.33%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.13%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.98%	95.50%

Plants that contains it

• Stenostomum acutatum

Cross-Links

• PubChem: 162906991
• LOTUS: LTS0243847
• wikiData: Q105176968