methyl (3aS,4S,5S,6E,11S,11aS)-5-[(2S)-butan-2-yl]oxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-11-hydroxy-3,10-dimethylidene-2-oxo-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-6-carboxylate

Details

• Internal ID: 3c46f667-747b-4ccc-9870-b8d4bea844d1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: methyl (3aS,4S,5S,6E,11S,11aS)-5-[(2S)-butan-2-yl]oxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-11-hydroxy-3,10-dimethylidene-2-oxo-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CCC(C)OC1C(C2C(C(C(=C)CCC=C1C(=O)OC)O)OC(=O)C2=C)OC(=O)C3(C(O3)C)C
• SMILES (Isomeric): CC[C@H](C)O[C@@H]/1[C@H]([C@@H]2[C@@H]([C@H](C(=C)CC/C=C1/C(=O)OC)O)OC(=O)C2=C)OC(=O)[C@@]3([C@@H](O3)C)C
• InChI: InChI=1S/C25H34O9/c1-8-13(3)31-19-16(23(28)30-7)11-9-10-12(2)18(26)20-17(14(4)22(27)32-20)21(19)33-24(29)25(6)15(5)34-25/h11,13,15,17-21,26H,2,4,8-10H2,1,3,5-7H3/b16-11+/t13-,15-,17-,18-,19-,20-,21-,25-/m0/s1
• InChI Key: GVFLFCFXOCAPCL-HVLCKYSYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₉
• Molecular Weight: 478.50 g/mol
• Exact Mass: 478.22028266 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9634	96.34%
Caco-2	-	0.6933	69.33%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6377	63.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8211	82.11%
OATP1B3 inhibitior	+	0.8795	87.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7175	71.75%
P-glycoprotein inhibitior	+	0.6705	67.05%
P-glycoprotein substrate	+	0.5969	59.69%
CYP3A4 substrate	+	0.6734	67.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	+	0.5260	52.60%
CYP2C9 inhibition	-	0.7227	72.27%
CYP2C19 inhibition	-	0.7554	75.54%
CYP2D6 inhibition	-	0.9141	91.41%
CYP1A2 inhibition	-	0.6896	68.96%
CYP2C8 inhibition	+	0.5157	51.57%
CYP inhibitory promiscuity	-	0.8366	83.66%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.4370	43.70%
Eye corrosion	-	0.9751	97.51%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.6536	65.36%
Skin corrosion	-	0.8946	89.46%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5157	51.57%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6139	61.39%
skin sensitisation	-	0.7710	77.10%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6346	63.46%
Acute Oral Toxicity (c)	III	0.4072	40.72%
Estrogen receptor binding	+	0.7608	76.08%
Androgen receptor binding	+	0.5805	58.05%
Thyroid receptor binding	+	0.5496	54.96%
Glucocorticoid receptor binding	+	0.7861	78.61%
Aromatase binding	+	0.6006	60.06%
PPAR gamma	+	0.7424	74.24%
Honey bee toxicity	-	0.7140	71.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8828	88.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.06%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.41%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.95%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.03%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.30%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.57%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.82%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.52%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.31%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.08%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.19%	95.89%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.11%	95.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.31%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	83.31%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	83.23%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.18%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.06%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.10%	96.47%
CHEMBL5028	O14672	ADAM10	81.84%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	81.06%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.66%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.50%	91.19%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.36%	95.71%

Plants that contains it

• Tetragonotheca repanda

Cross-Links

• PubChem: 162998881
• LOTUS: LTS0204449
• wikiData: Q105021124