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

Details

• Internal ID: cc6c8485-54bb-4a0d-bbc4-03e9535b0932
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (1R,2E,4S,6R,7E,9S,10S,11S)-9-[(2S,3R)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-3-methyl-10-[(2R)-2-methylbutanoyl]oxy-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(C=C(C3C(O3)C=C(C1OC(=O)C(C)(C(C)OC(=O)C)O)C(=O)OC)C)OC(=O)C2=C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(/[C@H]3[C@H](O3)/C=C(\[C@@H]1OC(=O)[C@](C)([C@@H](C)OC(=O)C)O)/C(=O)OC)\C)OC(=O)C2=C
• InChI: InChI=1S/C28H36O12/c1-9-12(2)24(30)39-23-20-14(4)25(31)38-18(20)10-13(3)21-19(37-21)11-17(26(32)35-8)22(23)40-27(33)28(7,34)15(5)36-16(6)29/h10-12,15,18-23,34H,4,9H2,1-3,5-8H3/b13-10+,17-11+/t12-,15-,18-,19-,20+,21+,22+,23+,28+/m1/s1
• InChI Key: HAIAVUKJFSLUSM-HNKIWCQXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₂
• Molecular Weight: 564.60 g/mol
• Exact Mass: 564.22067658 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9765	97.65%
Caco-2	-	0.7713	77.13%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5293	52.93%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.7917	79.17%
OATP1B3 inhibitior	+	0.8981	89.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7972	79.72%
P-glycoprotein inhibitior	+	0.8336	83.36%
P-glycoprotein substrate	+	0.6009	60.09%
CYP3A4 substrate	+	0.6819	68.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9053	90.53%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8159	81.59%
CYP2C19 inhibition	-	0.7863	78.63%
CYP2D6 inhibition	-	0.9241	92.41%
CYP1A2 inhibition	-	0.7855	78.55%
CYP2C8 inhibition	+	0.6715	67.15%
CYP inhibitory promiscuity	-	0.8432	84.32%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Danger	0.4196	41.96%
Eye corrosion	-	0.9665	96.65%
Eye irritation	-	0.8887	88.87%
Skin irritation	-	0.6764	67.64%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6241	62.41%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5836	58.36%
skin sensitisation	-	0.6424	64.24%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5735	57.35%
Acute Oral Toxicity (c)	III	0.4596	45.96%
Estrogen receptor binding	+	0.7955	79.55%
Androgen receptor binding	+	0.6377	63.77%
Thyroid receptor binding	+	0.5612	56.12%
Glucocorticoid receptor binding	+	0.7720	77.20%
Aromatase binding	+	0.5909	59.09%
PPAR gamma	+	0.6852	68.52%
Honey bee toxicity	-	0.7290	72.90%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9471	94.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	97.87%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.96%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.13%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.93%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.49%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.97%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.65%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	86.32%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.14%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.93%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.50%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.27%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.69%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.68%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.93%	90.93%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.28%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.85%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.02%	99.17%

Plants that contains it

• Melampodium americanum

Cross-Links

• PubChem: 163104227
• LOTUS: LTS0139549
• wikiData: Q105024889