[(3aS,6S,6aR,9S,9aS,9bR)-9-acetyloxy-6a-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,6,7,8,9,9b-octahydroazuleno[4,5-b]furan-9a-yl]methyl acetate

Details

• Internal ID: 3deef853-f74a-4c9b-8b85-e026dd04be28
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: [(3aS,6S,6aR,9S,9aS,9bR)-9-acetyloxy-6a-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,6,7,8,9,9b-octahydroazuleno[4,5-b]furan-9a-yl]methyl acetate
• SMILES (Canonical): CC1CCC2C(C3(C1(CCC3OC(=O)C)O)COC(=O)C)OC(=O)C2=C
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@H]([C@]3([C@]1(CC[C@@H]3OC(=O)C)O)COC(=O)C)OC(=O)C2=C
• InChI: InChI=1S/C19H26O7/c1-10-5-6-14-11(2)17(22)26-16(14)18(9-24-12(3)20)15(25-13(4)21)7-8-19(10,18)23/h10,14-16,23H,2,5-9H2,1,3-4H3/t10-,14-,15-,16+,18-,19+/m0/s1
• InChI Key: LBJJWDIRTIPLHE-UKEKVWLUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.16785316 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	+	0.5117	51.17%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7040	70.40%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8927	89.27%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6636	66.36%
BSEP inhibitior	-	0.7883	78.83%
P-glycoprotein inhibitior	-	0.6344	63.44%
P-glycoprotein substrate	-	0.7207	72.07%
CYP3A4 substrate	+	0.6324	63.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9008	90.08%
CYP3A4 inhibition	-	0.5886	58.86%
CYP2C9 inhibition	-	0.5807	58.07%
CYP2C19 inhibition	-	0.7801	78.01%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.5123	51.23%
CYP2C8 inhibition	-	0.6592	65.92%
CYP inhibitory promiscuity	-	0.9299	92.99%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6376	63.76%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.7696	76.96%
Skin irritation	+	0.5339	53.39%
Skin corrosion	-	0.9340	93.40%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6815	68.15%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5146	51.46%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5975	59.75%
Acute Oral Toxicity (c)	III	0.3719	37.19%
Estrogen receptor binding	+	0.8579	85.79%
Androgen receptor binding	+	0.5989	59.89%
Thyroid receptor binding	+	0.5668	56.68%
Glucocorticoid receptor binding	+	0.7043	70.43%
Aromatase binding	+	0.5467	54.67%
PPAR gamma	+	0.7364	73.64%
Honey bee toxicity	-	0.8201	82.01%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9905	99.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.42%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.30%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.68%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.70%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.10%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.78%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.14%	93.04%
CHEMBL2581	P07339	Cathepsin D	84.04%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.93%	92.62%
CHEMBL299	P17252	Protein kinase C alpha	83.08%	98.03%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.10%	94.80%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.87%	97.14%
CHEMBL5028	O14672	ADAM10	80.82%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.71%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.69%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.35%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.13%	91.07%

Plants that contains it

• Conchocarpus heterophyllus
• Parthenium alpinum
• Parthenium fruticosum
• Parthenium hysterophorus
• Parthenium lozanianum

Cross-Links

• PubChem: 101306774
• LOTUS: LTS0023391
• wikiData: Q105181999