methyl (3aS,4S,5R,6E,8R,10E,11aS)-8-hydroxy-10-(hydroxymethyl)-3-methylidene-4,5-bis(2-methylprop-2-enoyloxy)-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate

Details

• Internal ID: de928960-6e9b-4f30-9984-37d802d1373b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aS,4S,5R,6E,8R,10E,11aS)-8-hydroxy-10-(hydroxymethyl)-3-methylidene-4,5-bis(2-methylprop-2-enoyloxy)-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
• InChI: InChI=1S/C24H28O10/c1-11(2)21(27)33-19-16(24(30)31-6)9-15(26)7-14(10-25)8-17-18(13(5)23(29)32-17)20(19)34-22(28)12(3)4/h8-9,15,17-20,25-26H,1,3,5,7,10H2,2,4,6H3/b14-8+,16-9+/t15-,17+,18+,19-,20+/m1/s1
• InChI Key: AQNCURZHCFXQAV-NNYCIGDFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₀
• Molecular Weight: 476.50 g/mol
• Exact Mass: 476.16824709 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9429	94.29%
Caco-2	-	0.7462	74.62%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6015	60.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8470	84.70%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6171	61.71%
P-glycoprotein inhibitior	+	0.6575	65.75%
P-glycoprotein substrate	+	0.5641	56.41%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8800	88.00%
CYP3A4 inhibition	-	0.7444	74.44%
CYP2C9 inhibition	-	0.8700	87.00%
CYP2C19 inhibition	-	0.8776	87.76%
CYP2D6 inhibition	-	0.9305	93.05%
CYP1A2 inhibition	-	0.8165	81.65%
CYP2C8 inhibition	-	0.6020	60.20%
CYP inhibitory promiscuity	-	0.8991	89.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6476	64.76%
Eye corrosion	-	0.9741	97.41%
Eye irritation	-	0.8299	82.99%
Skin irritation	-	0.7445	74.45%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4320	43.20%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6099	60.99%
skin sensitisation	-	0.8422	84.22%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6351	63.51%
Acute Oral Toxicity (c)	III	0.4060	40.60%
Estrogen receptor binding	+	0.7175	71.75%
Androgen receptor binding	-	0.5133	51.33%
Thyroid receptor binding	+	0.5754	57.54%
Glucocorticoid receptor binding	+	0.7240	72.40%
Aromatase binding	-	0.5613	56.13%
PPAR gamma	+	0.7049	70.49%
Honey bee toxicity	-	0.7056	70.56%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.3780	37.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.76%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	89.79%	83.82%
CHEMBL2996	Q05655	Protein kinase C delta	88.88%	97.79%
CHEMBL2581	P07339	Cathepsin D	86.47%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	83.96%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.99%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.47%	95.89%

Plants that contains it

• Melampodium rosei

Cross-Links

• PubChem: 101532687
• LOTUS: LTS0180406
• wikiData: Q104916937