methyl (3aS,4S,5S,6E,10Z,11aR)-5-acetyloxy-4-[(2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate

Details

• Internal ID: 622cdb31-2b73-4d40-9080-d3a938ab1de6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aS,4S,5S,6E,10Z,11aR)-5-acetyloxy-4-[(2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CC(C(C)(C(=O)OC1C2C(C=C(CCC=C(C1OC(=O)C)C(=O)OC)CO)OC(=O)C2=C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]([C@@](C)(C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(/CC/C=C(\[C@@H]1OC(=O)C)/C(=O)OC)\CO)OC(=O)C2=C)O)OC(=O)C
• InChI: InChI=1S/C25H32O12/c1-12-19-18(36-22(12)29)10-16(11-26)8-7-9-17(23(30)33-6)20(35-15(4)28)21(19)37-24(31)25(5,32)13(2)34-14(3)27/h9-10,13,18-21,26,32H,1,7-8,11H2,2-6H3/b16-10-,17-9+/t13-,18+,19-,20-,21-,25-/m0/s1
• InChI Key: ACAVEPVIDDYXLW-PJTDGOTJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₂
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.18937645 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9156	91.56%
Caco-2	-	0.7714	77.14%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7446	74.46%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8483	84.83%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6771	67.71%
BSEP inhibitior	+	0.6712	67.12%
P-glycoprotein inhibitior	+	0.7762	77.62%
P-glycoprotein substrate	+	0.6020	60.20%
CYP3A4 substrate	+	0.6729	67.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.5899	58.99%
CYP2C9 inhibition	-	0.7091	70.91%
CYP2C19 inhibition	-	0.7889	78.89%
CYP2D6 inhibition	-	0.9172	91.72%
CYP1A2 inhibition	-	0.6554	65.54%
CYP2C8 inhibition	+	0.6083	60.83%
CYP inhibitory promiscuity	-	0.7894	78.94%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.5522	55.22%
Eye corrosion	-	0.9719	97.19%
Eye irritation	-	0.9196	91.96%
Skin irritation	-	0.6691	66.91%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6019	60.19%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5027	50.27%
skin sensitisation	-	0.8503	85.03%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5505	55.05%
Acute Oral Toxicity (c)	III	0.4550	45.50%
Estrogen receptor binding	+	0.7979	79.79%
Androgen receptor binding	+	0.5444	54.44%
Thyroid receptor binding	+	0.5334	53.34%
Glucocorticoid receptor binding	+	0.8405	84.05%
Aromatase binding	+	0.5786	57.86%
PPAR gamma	+	0.6729	67.29%
Honey bee toxicity	-	0.7135	71.35%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8823	88.23%

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	97.64%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.54%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.12%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.94%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.90%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	86.54%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.28%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.10%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.99%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.93%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.48%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.15%	94.33%
CHEMBL5028	O14672	ADAM10	82.25%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.17%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.79%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.62%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.21%	98.75%

Plants that contains it

• Tetragonotheca helianthoides

Cross-Links

• PubChem: 162978395
• LOTUS: LTS0144550
• wikiData: Q104908990