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

Details

• Internal ID: f47b7aa8-2e0a-44df-bcd9-242edda328cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aS,4S,5S,6E,10E,11aR)-4-[(2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-5-(3-hydroxy-3-methylbutanoyl)oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
• InChI: InChI=1S/C28H38O12/c1-14-10-9-11-18(25(32)36-8)22(39-20(30)13-27(5,6)34)23(21-15(2)24(31)38-19(21)12-14)40-26(33)28(7,35)16(3)37-17(4)29/h11-12,16,19,21-23,34-35H,2,9-10,13H2,1,3-8H3/b14-12+,18-11+/t16-,19+,21-,22-,23-,28-/m0/s1
• InChI Key: OOBGGZKARNTUOS-FMMLZWQHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₂
• Molecular Weight: 566.60 g/mol
• Exact Mass: 566.23632664 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9773	97.73%
Caco-2	-	0.7758	77.58%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5993	59.93%
OATP2B1 inhibitior	-	0.7174	71.74%
OATP1B1 inhibitior	+	0.8404	84.04%
OATP1B3 inhibitior	+	0.8586	85.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8236	82.36%
P-glycoprotein inhibitior	+	0.8282	82.82%
P-glycoprotein substrate	+	0.6019	60.19%
CYP3A4 substrate	+	0.6852	68.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9129	91.29%
CYP3A4 inhibition	-	0.5809	58.09%
CYP2C9 inhibition	-	0.8057	80.57%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9155	91.55%
CYP1A2 inhibition	-	0.7374	73.74%
CYP2C8 inhibition	+	0.6326	63.26%
CYP inhibitory promiscuity	-	0.9293	92.93%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5282	52.82%
Eye corrosion	-	0.9769	97.69%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.5744	57.44%
Skin corrosion	-	0.8826	88.26%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5293	52.93%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5348	53.48%
skin sensitisation	-	0.7224	72.24%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5820	58.20%
Acute Oral Toxicity (c)	III	0.4058	40.58%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	+	0.5490	54.90%
Thyroid receptor binding	+	0.5986	59.86%
Glucocorticoid receptor binding	+	0.7975	79.75%
Aromatase binding	+	0.6713	67.13%
PPAR gamma	+	0.7316	73.16%
Honey bee toxicity	-	0.6957	69.57%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9006	90.06%

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	96.98%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.65%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.03%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.01%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.97%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	93.75%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.87%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.29%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.08%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.94%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.80%	94.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.17%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.11%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	84.03%	97.79%
CHEMBL5028	O14672	ADAM10	83.63%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.42%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.88%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.78%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	81.02%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.58%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.49%	91.07%

Plants that contains it

• Tetragonotheca helianthoides

Cross-Links

• PubChem: 163056094
• LOTUS: LTS0015749
• wikiData: Q105195280