[(3aS,4S,6R,9R,10R,11aR)-6-acetyloxy-9-methoxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylbut-2-enoate

Details

• Internal ID: 81bce133-2c4b-4977-b0dd-bbf312f6dfc5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4S,6R,9R,10R,11aR)-6-acetyloxy-9-methoxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C(=O)CC(C(CC2C1C(=C)C(=O)O2)C)OC)(C)OC(=O)C
• SMILES (Isomeric): CC=C(C)C(=O)O[C@H]1C[C@@](C(=O)C[C@H]([C@@H](C[C@@H]2[C@@H]1C(=C)C(=O)O2)C)OC)(C)OC(=O)C
• InChI: InChI=1S/C23H32O8/c1-8-12(2)21(26)30-18-11-23(6,31-15(5)24)19(25)10-16(28-7)13(3)9-17-20(18)14(4)22(27)29-17/h8,13,16-18,20H,4,9-11H2,1-3,5-7H3/t13-,16-,17-,18+,20+,23-/m1/s1
• InChI Key: LUCNCJMEFWUKSZ-METIUIJESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₈
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.20971797 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.6004	60.04%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5642	56.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8588	85.88%
OATP1B3 inhibitior	+	0.8746	87.46%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8416	84.16%
P-glycoprotein inhibitior	+	0.8174	81.74%
P-glycoprotein substrate	-	0.5743	57.43%
CYP3A4 substrate	+	0.6585	65.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9041	90.41%
CYP3A4 inhibition	-	0.6851	68.51%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.8510	85.10%
CYP2D6 inhibition	-	0.9684	96.84%
CYP1A2 inhibition	-	0.5641	56.41%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9371	93.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5646	56.46%
Eye corrosion	-	0.9713	97.13%
Eye irritation	-	0.8456	84.56%
Skin irritation	-	0.6164	61.64%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6957	69.57%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6749	67.49%
skin sensitisation	-	0.7262	72.62%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8942	89.42%
Acute Oral Toxicity (c)	III	0.3771	37.71%
Estrogen receptor binding	+	0.8209	82.09%
Androgen receptor binding	+	0.6105	61.05%
Thyroid receptor binding	+	0.6076	60.76%
Glucocorticoid receptor binding	+	0.7438	74.38%
Aromatase binding	+	0.6097	60.97%
PPAR gamma	+	0.6912	69.12%
Honey bee toxicity	-	0.5969	59.69%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	97.71%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.33%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.19%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.31%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.38%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	90.33%	97.79%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.69%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	86.26%	90.17%
CHEMBL1902	P62942	FK506-binding protein 1A	84.88%	97.05%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.74%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.58%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.23%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.98%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.88%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.98%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.71%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.63%	89.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.23%	96.39%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.15%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.06%	100.00%

Plants that contains it

• Piptocoma rufescens

Cross-Links

• PubChem: 162919377
• LOTUS: LTS0194299
• wikiData: Q105157316