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

Details

• Internal ID: 1be5c9b9-4a10-4667-8993-ad885bbd05cb
• 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,11R)-10-[(2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-3-methyl-9-[(E)-2-methylbut-2-enoyl]oxy-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2C(C=C(C3C(O3)C=C1C(=O)OC)C)OC(=O)C2=C)OC(=O)C(C)(C(C)OC(=O)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]/1[C@H]([C@H]2[C@@H](/C=C(/[C@H]3[C@H](O3)/C=C1/C(=O)OC)\C)OC(=O)C2=C)OC(=O)[C@](C)([C@H](C)OC(=O)C)O
• InChI: InChI=1S/C28H34O12/c1-9-12(2)24(30)39-22-17(26(32)35-8)11-19-21(37-19)13(3)10-18-20(14(4)25(31)38-18)23(22)40-27(33)28(7,34)15(5)36-16(6)29/h9-11,15,18-23,34H,4H2,1-3,5-8H3/b12-9+,13-10+,17-11+/t15-,18+,19+,20+,21-,22-,23-,28-/m0/s1
• InChI Key: IPDIYYIXBGPPQF-YEHCFEOHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₂
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.20502652 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.40
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9680	96.80%
Caco-2	-	0.7683	76.83%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6082	60.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8121	81.21%
OATP1B3 inhibitior	+	0.9123	91.23%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7701	77.01%
P-glycoprotein inhibitior	+	0.8470	84.70%
P-glycoprotein substrate	+	0.5709	57.09%
CYP3A4 substrate	+	0.6813	68.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9094	90.94%
CYP3A4 inhibition	-	0.5832	58.32%
CYP2C9 inhibition	-	0.9160	91.60%
CYP2C19 inhibition	-	0.8460	84.60%
CYP2D6 inhibition	-	0.9357	93.57%
CYP1A2 inhibition	-	0.8219	82.19%
CYP2C8 inhibition	+	0.6452	64.52%
CYP inhibitory promiscuity	-	0.8982	89.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Danger	0.4862	48.62%
Eye corrosion	-	0.9555	95.55%
Eye irritation	-	0.8826	88.26%
Skin irritation	-	0.6822	68.22%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5901	59.01%
skin sensitisation	-	0.6667	66.67%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7016	70.16%
Acute Oral Toxicity (c)	III	0.3675	36.75%
Estrogen receptor binding	+	0.7696	76.96%
Androgen receptor binding	+	0.5986	59.86%
Thyroid receptor binding	+	0.5956	59.56%
Glucocorticoid receptor binding	+	0.7637	76.37%
Aromatase binding	+	0.5212	52.12%
PPAR gamma	+	0.6864	68.64%
Honey bee toxicity	-	0.6627	66.27%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8725	87.25%

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	98.24%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.68%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.95%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.53%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.50%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.02%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.96%	97.14%
CHEMBL2581	P07339	Cathepsin D	84.72%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.66%	91.07%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.06%	97.36%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.81%	89.34%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.74%	81.11%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.54%	93.03%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.89%	90.93%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.59%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.04%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.01%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.43%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.27%	98.75%

Plants that contains it

• Melampodium americanum

Cross-Links

• PubChem: 162932695
• LOTUS: LTS0147372
• wikiData: Q105117170