[(3aS,5S,6E,9R,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-5-yl] 2-(4-methoxyphenyl)acetate

Details

• Internal ID: cfc7c7cb-39b3-421b-b5a8-989c949f827f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,5S,6E,9R,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-5-yl] 2-(4-methoxyphenyl)acetate
• SMILES (Canonical): CC1=CCC(C(=CC2C(CC1OC(=O)CC3=CC=C(C=C3)OC)C(=C)C(=O)O2)C)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C/C/1=C\C[C@H](/C(=C/[C@@H]2[C@@H](C[C@@H]1OC(=O)CC3=CC=C(C=C3)OC)C(=C)C(=O)O2)/C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C30H38O11/c1-15-5-10-21(40-30-28(35)27(34)26(33)24(14-31)41-30)16(2)11-23-20(17(3)29(36)39-23)13-22(15)38-25(32)12-18-6-8-19(37-4)9-7-18/h5-9,11,20-24,26-28,30-31,33-35H,3,10,12-14H2,1-2,4H3/b15-5+,16-11+/t20-,21+,22-,23+,24+,26+,27-,28+,30+/m0/s1
• InChI Key: NOBPRNPEBCFZMU-QLJMVRKSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₁
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.24141202 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8144	81.44%
Caco-2	-	0.8452	84.52%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6606	66.06%
OATP2B1 inhibitior	-	0.8668	86.68%
OATP1B1 inhibitior	+	0.8172	81.72%
OATP1B3 inhibitior	+	0.9120	91.20%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9392	93.92%
P-glycoprotein inhibitior	+	0.6608	66.08%
P-glycoprotein substrate	-	0.6181	61.81%
CYP3A4 substrate	+	0.6902	69.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8771	87.71%
CYP3A4 inhibition	-	0.7826	78.26%
CYP2C9 inhibition	-	0.8540	85.40%
CYP2C19 inhibition	-	0.7817	78.17%
CYP2D6 inhibition	-	0.9027	90.27%
CYP1A2 inhibition	-	0.8042	80.42%
CYP2C8 inhibition	+	0.5998	59.98%
CYP inhibitory promiscuity	-	0.7339	73.39%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7003	70.03%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.7555	75.55%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7870	78.70%
Micronuclear	-	0.5626	56.26%
Hepatotoxicity	-	0.5696	56.96%
skin sensitisation	-	0.8170	81.70%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7667	76.67%
Acute Oral Toxicity (c)	III	0.4498	44.98%
Estrogen receptor binding	+	0.8536	85.36%
Androgen receptor binding	+	0.6121	61.21%
Thyroid receptor binding	+	0.5529	55.29%
Glucocorticoid receptor binding	+	0.7503	75.03%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7084	70.84%
Honey bee toxicity	-	0.6980	69.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9770	97.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.32%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.69%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.06%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.96%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.59%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	93.13%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.55%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.11%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.98%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.64%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.30%	90.00%
CHEMBL2581	P07339	Cathepsin D	91.27%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.24%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.35%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.54%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.48%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.58%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.45%	97.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.41%	91.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.59%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.30%	95.83%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.17%	93.00%

Plants that contains it

• Sonchus oleraceus

Cross-Links

• PubChem: 163191169
• LOTUS: LTS0047204
• wikiData: Q105182456