methyl (3aS,4S,5R,6E,10E,11aR)-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: c66a113f-aee7-419a-96b1-c46415cbdc3c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aS,4S,5R,6E,10E,11aR)-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/C24H28O9/c1-12(2)21(26)32-19-16(24(29)30-6)9-7-8-15(11-25)10-17-18(14(5)23(28)31-17)20(19)33-22(27)13(3)4/h9-10,17-20,25H,1,3,5,7-8,11H2,2,4,6H3/b15-10+,16-9+/t17-,18+,19-,20+/m1/s1
• InChI Key: TZWQGZRXPQFHSI-ARXITZDXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₉
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.17333247 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9413	94.13%
Caco-2	-	0.6811	68.11%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7450	74.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8730	87.30%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.8012	80.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6522	65.22%
P-glycoprotein inhibitior	+	0.6592	65.92%
P-glycoprotein substrate	-	0.5245	52.45%
CYP3A4 substrate	+	0.6419	64.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.5750	57.50%
CYP2C9 inhibition	-	0.7265	72.65%
CYP2C19 inhibition	-	0.7503	75.03%
CYP2D6 inhibition	-	0.9150	91.50%
CYP1A2 inhibition	-	0.5324	53.24%
CYP2C8 inhibition	+	0.4536	45.36%
CYP inhibitory promiscuity	-	0.7991	79.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.6337	63.37%
Eye corrosion	-	0.9566	95.66%
Eye irritation	-	0.8270	82.70%
Skin irritation	-	0.7032	70.32%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4599	45.99%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5757	57.57%
skin sensitisation	-	0.8398	83.98%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6247	62.47%
Acute Oral Toxicity (c)	III	0.4426	44.26%
Estrogen receptor binding	+	0.6407	64.07%
Androgen receptor binding	-	0.4865	48.65%
Thyroid receptor binding	+	0.5524	55.24%
Glucocorticoid receptor binding	+	0.7291	72.91%
Aromatase binding	-	0.5887	58.87%
PPAR gamma	+	0.7458	74.58%
Honey bee toxicity	-	0.7607	76.07%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8741	87.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.82%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.57%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.60%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.61%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.47%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.64%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.02%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.91%	94.33%

Plants that contains it

• Melampodium rosei

Cross-Links

• PubChem: 163185699
• LOTUS: LTS0113232
• wikiData: Q105268458