[(3aS,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 0c30c343-1f78-4f6d-a64a-365f0410a752
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(CO)C(=O)OC1C2C(CC(C=CC(=O)C(C1OC(=O)C)(C)O)C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(\CO)/C(=O)O[C@H]1[C@@H]2[C@@H](C[C@H](/C=C\C(=O)[C@]([C@@H]1OC(=O)C)(C)O)C)OC(=O)C2=C
• InChI: InChI=1S/C22H28O9/c1-6-14(10-23)21(27)31-18-17-12(3)20(26)30-15(17)9-11(2)7-8-16(25)22(5,28)19(18)29-13(4)24/h6-8,11,15,17-19,23,28H,3,9-10H2,1-2,4-5H3/b8-7-,14-6+/t11-,15+,17-,18-,19+,22-/m0/s1
• InChI Key: ASMHVEGKRVKAPP-QJYFQJJASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₉
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.17333247 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9750	97.50%
Caco-2	-	0.5581	55.81%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6360	63.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8411	84.11%
OATP1B3 inhibitior	+	0.8796	87.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5405	54.05%
P-glycoprotein inhibitior	+	0.6854	68.54%
P-glycoprotein substrate	-	0.5403	54.03%
CYP3A4 substrate	+	0.6465	64.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9136	91.36%
CYP3A4 inhibition	-	0.7925	79.25%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.8916	89.16%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.7347	73.47%
CYP2C8 inhibition	-	0.6115	61.15%
CYP inhibitory promiscuity	-	0.8876	88.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5564	55.64%
Eye corrosion	-	0.9755	97.55%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.6108	61.08%
Skin corrosion	-	0.9263	92.63%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5947	59.47%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7551	75.51%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4908	49.08%
Acute Oral Toxicity (c)	III	0.5075	50.75%
Estrogen receptor binding	+	0.6691	66.91%
Androgen receptor binding	+	0.5261	52.61%
Thyroid receptor binding	+	0.5437	54.37%
Glucocorticoid receptor binding	+	0.7380	73.80%
Aromatase binding	-	0.5144	51.44%
PPAR gamma	+	0.6356	63.56%
Honey bee toxicity	-	0.6861	68.61%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9311	93.11%

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	99.07%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.65%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	94.39%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.60%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.33%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.39%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.18%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.55%	89.34%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.10%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.50%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.10%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	86.99%	98.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.41%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.25%	85.14%
CHEMBL2581	P07339	Cathepsin D	84.94%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.14%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.79%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.92%	89.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.59%	95.50%
CHEMBL5028	O14672	ADAM10	80.80%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.35%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.07%	95.89%

Plants that contains it

• Neurolaena lobata

Cross-Links

• PubChem: 162844856
• LOTUS: LTS0034876
• wikiData: Q104917930