[(3aS,4S,5R,6R,9E,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-4-(2-methylpropoxy)-2,7-dioxo-3a,4,5,8,11,11a-hexahydrocyclodeca[b]furan-5-yl] acetate

Details

• Internal ID: be9ab5f4-528c-4368-954f-49f4fd211b71
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4S,5R,6R,9E,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-4-(2-methylpropoxy)-2,7-dioxo-3a,4,5,8,11,11a-hexahydrocyclodeca[b]furan-5-yl] acetate
• SMILES (Canonical): CC1=CCC(=O)C(C(C(C2C(C1)OC(=O)C2=C)OCC(C)C)OC(=O)C)(C)O
• SMILES (Isomeric): C/C/1=C\CC(=O)[C@]([C@@H]([C@H]([C@@H]2[C@@H](C1)OC(=O)C2=C)OCC(C)C)OC(=O)C)(C)O
• InChI: InChI=1S/C21H30O7/c1-11(2)10-26-18-17-13(4)20(24)28-15(17)9-12(3)7-8-16(23)21(6,25)19(18)27-14(5)22/h7,11,15,17-19,25H,4,8-10H2,1-3,5-6H3/b12-7+/t15-,17+,18+,19-,21+/m1/s1
• InChI Key: FWZYOHZELZBVFT-COUHFJOVSA-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: 1.90
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	+	0.6750	67.50%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7690	76.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9128	91.28%
OATP1B3 inhibitior	+	0.8947	89.47%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6428	64.28%
P-glycoprotein inhibitior	+	0.6475	64.75%
P-glycoprotein substrate	-	0.6245	62.45%
CYP3A4 substrate	+	0.6400	64.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8955	89.55%
CYP3A4 inhibition	-	0.7383	73.83%
CYP2C9 inhibition	-	0.6980	69.80%
CYP2C19 inhibition	-	0.8167	81.67%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	-	0.7132	71.32%
CYP2C8 inhibition	-	0.6967	69.67%
CYP inhibitory promiscuity	-	0.9007	90.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5751	57.51%
Eye corrosion	-	0.9726	97.26%
Eye irritation	-	0.9001	90.01%
Skin irritation	-	0.6326	63.26%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5291	52.91%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7017	70.17%
skin sensitisation	-	0.7108	71.08%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.8989	89.89%
Acute Oral Toxicity (c)	III	0.4882	48.82%
Estrogen receptor binding	+	0.6790	67.90%
Androgen receptor binding	+	0.6442	64.42%
Thyroid receptor binding	-	0.5230	52.30%
Glucocorticoid receptor binding	+	0.7316	73.16%
Aromatase binding	-	0.4846	48.46%
PPAR gamma	+	0.7282	72.82%
Honey bee toxicity	-	0.7455	74.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9895	98.95%

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	97.22%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.21%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.99%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.83%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.92%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.85%	97.79%
CHEMBL2581	P07339	Cathepsin D	91.74%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.59%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.54%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.88%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.07%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.90%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.11%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.92%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	81.84%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	81.73%	90.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.62%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	81.52%	94.73%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.13%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.56%	95.89%
CHEMBL5028	O14672	ADAM10	80.29%	97.50%

Plants that contains it

• Neurolaena oaxacana

Cross-Links

• PubChem: 101035411
• LOTUS: LTS0187115
• wikiData: Q105003765