[(3aR,5R,5aS,6R,7R,8R,8aS,9aR)-8-acetyloxy-7-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate

Details

• Internal ID: 91e4ecdb-9045-478b-810b-52ca23a583f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: [(3aR,5R,5aS,6R,7R,8R,8aS,9aR)-8-acetyloxy-7-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate
• SMILES (Canonical): CC1CC2C(CC3(C1C(C(C3OC(=O)C)O)OC(=O)C)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@H](C[C@]3([C@H]1[C@H]([C@H]([C@@H]3OC(=O)C)O)OC(=O)C)C)C(=C)C(=O)O2
• InChI: InChI=1S/C19H26O7/c1-8-6-13-12(9(2)18(23)26-13)7-19(5)14(8)16(24-10(3)20)15(22)17(19)25-11(4)21/h8,12-17,22H,2,6-7H2,1,3-5H3/t8-,12-,13-,14-,15-,16-,17+,19+/m1/s1
• InChI Key: IHXCPSFDIYQBBD-KKMGJOHJSA-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: 1.90
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9575	95.75%
Caco-2	-	0.5388	53.88%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6136	61.36%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8702	87.02%
OATP1B3 inhibitior	+	0.8828	88.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9129	91.29%
P-glycoprotein inhibitior	-	0.5407	54.07%
P-glycoprotein substrate	-	0.7948	79.48%
CYP3A4 substrate	+	0.6490	64.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.5714	57.14%
CYP2C9 inhibition	-	0.8134	81.34%
CYP2C19 inhibition	-	0.7588	75.88%
CYP2D6 inhibition	-	0.9610	96.10%
CYP1A2 inhibition	-	0.5489	54.89%
CYP2C8 inhibition	-	0.7398	73.98%
CYP inhibitory promiscuity	-	0.9272	92.72%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.5018	50.18%
Eye corrosion	-	0.9755	97.55%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.5778	57.78%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6300	63.00%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.7420	74.20%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.8134	81.34%
Acute Oral Toxicity (c)	II	0.5132	51.32%
Estrogen receptor binding	+	0.7928	79.28%
Androgen receptor binding	+	0.5706	57.06%
Thyroid receptor binding	+	0.5388	53.88%
Glucocorticoid receptor binding	+	0.5593	55.93%
Aromatase binding	-	0.5378	53.78%
PPAR gamma	+	0.6276	62.76%
Honey bee toxicity	-	0.6135	61.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9883	98.83%

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	97.63%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.08%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.70%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.41%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.71%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.35%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.99%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.25%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.10%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.80%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.34%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	83.23%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	83.21%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.16%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.96%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	81.91%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	81.28%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.57%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.53%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.24%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.03%	94.80%

Plants that contains it

• Hymenoxys subintegra

Cross-Links

• PubChem: 163186558
• LOTUS: LTS0104177
• wikiData: Q105113297