methyl (3aR,4R,6E,10R,11aR)-10-(hydroxymethyl)-4-(3-methylbutanoyloxy)-3-methylidene-2-oxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-6-carboxylate

Details

• Internal ID: ed72ac10-5a5b-470e-8f6b-5c414506baa4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aR,4R,6E,10R,11aR)-10-(hydroxymethyl)-4-(3-methylbutanoyloxy)-3-methylidene-2-oxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CC(C)CC(=O)OC1CC(=CCCC(CC2C1C(=C)C(=O)O2)CO)C(=O)OC
• SMILES (Isomeric): CC(C)CC(=O)O[C@@H]1C/C(=C\CC[C@H](C[C@@H]2[C@H]1C(=C)C(=O)O2)CO)/C(=O)OC
• InChI: InChI=1S/C21H30O7/c1-12(2)8-18(23)27-17-10-15(21(25)26-4)7-5-6-14(11-22)9-16-19(17)13(3)20(24)28-16/h7,12,14,16-17,19,22H,3,5-6,8-11H2,1-2,4H3/b15-7+/t14-,16-,17-,19-/m1/s1
• InChI Key: RROQBGLSWSIRDJ-YUTSCNQYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₇
• Molecular Weight: 394.50 g/mol
• Exact Mass: 394.19915329 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9633	96.33%
Caco-2	+	0.5297	52.97%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7963	79.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8423	84.23%
OATP1B3 inhibitior	+	0.9020	90.20%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.5973	59.73%
P-glycoprotein inhibitior	-	0.5879	58.79%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	+	0.5479	54.79%
CYP2C9 inhibition	-	0.7063	70.63%
CYP2C19 inhibition	-	0.7828	78.28%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	+	0.5288	52.88%
CYP2C8 inhibition	+	0.4848	48.48%
CYP inhibitory promiscuity	-	0.8666	86.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9764	97.64%
Eye irritation	-	0.8401	84.01%
Skin irritation	-	0.7186	71.86%
Skin corrosion	-	0.9540	95.40%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4702	47.02%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.8510	85.10%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.8646	86.46%
Acute Oral Toxicity (c)	III	0.4322	43.22%
Estrogen receptor binding	+	0.5360	53.60%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5853	58.53%
Glucocorticoid receptor binding	+	0.7232	72.32%
Aromatase binding	-	0.5519	55.19%
PPAR gamma	-	0.5407	54.07%
Honey bee toxicity	-	0.7906	79.06%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9647	96.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.44%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.71%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.61%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.88%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	91.22%	90.17%
CHEMBL2581	P07339	Cathepsin D	88.79%	98.95%
CHEMBL4072	P07858	Cathepsin B	88.40%	93.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.29%	85.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.85%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.75%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.56%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.70%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.29%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.71%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.52%	92.88%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.03%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.44%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.34%	99.17%
CHEMBL299	P17252	Protein kinase C alpha	80.28%	98.03%

Plants that contains it

• Melampodium leucanthum

Cross-Links

• PubChem: 101708813
• LOTUS: LTS0027933
• wikiData: Q105244272