methyl (1R,2Z,4S,6R,7E,9S,10S,11S)-9-acetyloxy-10-[(2R,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate

Details

• Internal ID: 74c43937-dc12-42fe-9af3-cd840c4abd3c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (1R,2Z,4S,6R,7E,9S,10S,11S)-9-acetyloxy-10-[(2R,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2C3C(C=C(C4C(O4)C=C(C2OC(=O)C)C(=O)OC)C)OC(=O)C3=C
• SMILES (Isomeric): C[C@H]1[C@](O1)(C)C(=O)O[C@H]2[C@@H]3[C@@H](/C=C(\[C@H]4[C@H](O4)/C=C(\[C@@H]2OC(=O)C)/C(=O)OC)/C)OC(=O)C3=C
• InChI: InChI=1S/C23H26O10/c1-9-7-14-16(10(2)20(25)31-14)19(32-22(27)23(5)11(3)33-23)18(29-12(4)24)13(21(26)28-6)8-15-17(9)30-15/h7-8,11,14-19H,2H2,1,3-6H3/b9-7-,13-8+/t11-,14+,15+,16-,17-,18-,19-,23+/m0/s1
• InChI Key: SDWFMFKVWKMICC-GHPQAWDWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₀
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.15259702 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9797	97.97%
Caco-2	-	0.5543	55.43%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5676	56.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8082	80.82%
OATP1B3 inhibitior	+	0.9328	93.28%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5231	52.31%
P-glycoprotein inhibitior	+	0.7851	78.51%
P-glycoprotein substrate	+	0.5149	51.49%
CYP3A4 substrate	+	0.6823	68.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9085	90.85%
CYP3A4 inhibition	-	0.5334	53.34%
CYP2C9 inhibition	-	0.9230	92.30%
CYP2C19 inhibition	-	0.7897	78.97%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.7365	73.65%
CYP2C8 inhibition	+	0.5384	53.84%
CYP inhibitory promiscuity	-	0.7858	78.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.4081	40.81%
Eye corrosion	-	0.9439	94.39%
Eye irritation	-	0.8068	80.68%
Skin irritation	-	0.7124	71.24%
Skin corrosion	-	0.9333	93.33%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6856	68.56%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6065	60.65%
skin sensitisation	-	0.6222	62.22%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6005	60.05%
Acute Oral Toxicity (c)	III	0.3855	38.55%
Estrogen receptor binding	+	0.8024	80.24%
Androgen receptor binding	+	0.6130	61.30%
Thyroid receptor binding	+	0.5896	58.96%
Glucocorticoid receptor binding	+	0.6747	67.47%
Aromatase binding	+	0.5744	57.44%
PPAR gamma	+	0.7586	75.86%
Honey bee toxicity	-	0.6913	69.13%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9088	90.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.93%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.77%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.59%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	90.65%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.21%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.62%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.32%	97.14%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.42%	81.11%
CHEMBL2581	P07339	Cathepsin D	84.86%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.45%	93.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.21%	85.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.98%	94.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.54%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	81.78%	97.79%
CHEMBL5028	O14672	ADAM10	81.20%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.13%	97.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.48%	91.19%

Plants that contains it

• Melampodium leucanthum

Cross-Links

• PubChem: 132561056
• LOTUS: LTS0013260
• wikiData: Q105250889