[6-[(5,8-dimethyl-1-methylidene-2-oxo-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,7-b]furan-8-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 97c8c3ae-48a1-4f0b-b0c1-a5ef48502952
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [6-[(5,8-dimethyl-1-methylidene-2-oxo-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,7-b]furan-8-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1=CC2C(CC3C1CCC3(C)OC4C(C(C(C(O4)COC(=O)C)O)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): CC1=CC2C(CC3C1CCC3(C)OC4C(C(C(C(O4)COC(=O)C)O)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C23H32O9/c1-10-7-16-14(11(2)21(28)30-16)8-15-13(10)5-6-23(15,4)32-22-20(27)19(26)18(25)17(31-22)9-29-12(3)24/h7,13-20,22,25-27H,2,5-6,8-9H2,1,3-4H3
• InChI Key: DYLLAMCKQXNEAV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₉
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.20463259 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7871	78.71%
Caco-2	-	0.7645	76.45%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8071	80.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7830	78.30%
OATP1B3 inhibitior	+	0.9230	92.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7521	75.21%
BSEP inhibitior	-	0.7235	72.35%
P-glycoprotein inhibitior	-	0.6006	60.06%
P-glycoprotein substrate	-	0.7811	78.11%
CYP3A4 substrate	+	0.6968	69.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8996	89.96%
CYP3A4 inhibition	-	0.8810	88.10%
CYP2C9 inhibition	-	0.7451	74.51%
CYP2C19 inhibition	-	0.8381	83.81%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.7639	76.39%
CYP2C8 inhibition	+	0.5670	56.70%
CYP inhibitory promiscuity	-	0.9301	93.01%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6466	64.66%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9523	95.23%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5477	54.77%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8968	89.68%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8788	87.88%
Acute Oral Toxicity (c)	III	0.4295	42.95%
Estrogen receptor binding	+	0.7782	77.82%
Androgen receptor binding	+	0.6185	61.85%
Thyroid receptor binding	+	0.5177	51.77%
Glucocorticoid receptor binding	+	0.5866	58.66%
Aromatase binding	+	0.5407	54.07%
PPAR gamma	+	0.6105	61.05%
Honey bee toxicity	-	0.7292	72.92%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9886	98.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.69%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	97.43%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.51%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.76%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.70%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.67%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.47%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.72%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.19%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.01%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.88%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.20%	97.36%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.18%	94.80%
CHEMBL221	P23219	Cyclooxygenase-1	85.12%	90.17%
CHEMBL5255	O00206	Toll-like receptor 4	84.70%	92.50%
CHEMBL1937	Q92769	Histone deacetylase 2	83.97%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.48%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.72%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.00%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	80.77%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.34%	99.23%
CHEMBL5957	P21589	5'-nucleotidase	80.30%	97.78%
CHEMBL5028	O14672	ADAM10	80.24%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.05%	97.33%

Plants that contains it

• Helenium donianum
• Hymenoxys lemmonii

Cross-Links

• PubChem: 14527112
• LOTUS: LTS0113733
• wikiData: Q104991414