[5-Acetyloxy-6-[(6-acetyloxy-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl)oxy]-3,4-dihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: be2e9e76-68c7-43c1-b842-5395400c3773
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [5-acetyloxy-6-[(6-acetyloxy-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl)oxy]-3,4-dihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(CC(C3C2CC4C(CC3=C)OC(=O)C4=C)OC(=O)C)C)OC(=O)C)O)O
• SMILES (Isomeric): CC(=O)OCC1C(C(C(C(O1)OC2(CC(C3C2CC4C(CC3=C)OC(=O)C4=C)OC(=O)C)C)OC(=O)C)O)O
• InChI: InChI=1S/C27H36O12/c1-11-7-18-16(12(2)25(33)37-18)8-17-21(11)19(35-14(4)29)9-27(17,6)39-26-24(36-15(5)30)23(32)22(31)20(38-26)10-34-13(3)28/h16-24,26,31-32H,1-2,7-10H2,3-6H3
• InChI Key: YGZJQUBWZFNBSN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₂
• Molecular Weight: 552.60 g/mol
• Exact Mass: 552.22067658 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9050	90.50%
Caco-2	-	0.8146	81.46%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7917	79.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8164	81.64%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6186	61.86%
P-glycoprotein inhibitior	+	0.6565	65.65%
P-glycoprotein substrate	-	0.6099	60.99%
CYP3A4 substrate	+	0.6986	69.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8996	89.96%
CYP3A4 inhibition	-	0.7244	72.44%
CYP2C9 inhibition	-	0.7963	79.63%
CYP2C19 inhibition	-	0.8268	82.68%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.7711	77.11%
CYP2C8 inhibition	+	0.5322	53.22%
CYP inhibitory promiscuity	-	0.9320	93.20%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6278	62.78%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9080	90.80%
Skin irritation	-	0.5498	54.98%
Skin corrosion	-	0.9352	93.52%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5850	58.50%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8653	86.53%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5190	51.90%
Acute Oral Toxicity (c)	III	0.4844	48.44%
Estrogen receptor binding	+	0.7356	73.56%
Androgen receptor binding	+	0.6615	66.15%
Thyroid receptor binding	-	0.5131	51.31%
Glucocorticoid receptor binding	+	0.6847	68.47%
Aromatase binding	+	0.6469	64.69%
PPAR gamma	+	0.6288	62.88%
Honey bee toxicity	-	0.6274	62.74%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	98.57%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.03%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.63%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.33%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.78%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	94.26%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.86%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.84%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	89.13%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.69%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	88.43%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.53%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.31%	95.50%
CHEMBL299	P17252	Protein kinase C alpha	84.15%	98.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.58%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.49%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	81.75%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.32%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.01%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.27%	89.34%

Plants that contains it

• Curio talinoides
• Senecio crassissimus
• Tetraneuris ivesiana

Cross-Links

• PubChem: 163016634
• LOTUS: LTS0002928
• wikiData: Q104983592