[4-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-6-yl]-4-hydroxybutan-2-yl] acetate

Details

• Internal ID: 163daad2-d498-49b1-9f0a-98af32de8fc5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: [4-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-6-yl]-4-hydroxybutan-2-yl] acetate
• SMILES (Canonical): CC1CC2C(CC=C1C(CC(C)OC(=O)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H](CC=C1C(CC(C)OC(=O)C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C17H24O5/c1-9-7-16-14(11(3)17(20)22-16)6-5-13(9)15(19)8-10(2)21-12(4)18/h5,9-10,14-16,19H,3,6-8H2,1-2,4H3/t9-,10?,14+,15?,16-/m0/s1
• InChI Key: IQAWVYINTAIBSH-HPJQFELNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.14
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9713	97.13%
Caco-2	-	0.5427	54.27%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5523	55.23%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8866	88.66%
OATP1B3 inhibitior	+	0.9175	91.75%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7651	76.51%
P-glycoprotein inhibitior	-	0.7896	78.96%
P-glycoprotein substrate	-	0.6227	62.27%
CYP3A4 substrate	+	0.6118	61.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	+	0.5898	58.98%
CYP2C9 inhibition	-	0.8053	80.53%
CYP2C19 inhibition	-	0.7672	76.72%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.6798	67.98%
CYP2C8 inhibition	-	0.7589	75.89%
CYP inhibitory promiscuity	-	0.8813	88.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5966	59.66%
Eye corrosion	-	0.9706	97.06%
Eye irritation	-	0.6646	66.46%
Skin irritation	-	0.6147	61.47%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6068	60.68%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7140	71.40%
skin sensitisation	-	0.7596	75.96%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	II	0.4876	48.76%
Estrogen receptor binding	+	0.5682	56.82%
Androgen receptor binding	-	0.5522	55.22%
Thyroid receptor binding	-	0.5073	50.73%
Glucocorticoid receptor binding	+	0.5635	56.35%
Aromatase binding	-	0.6253	62.53%
PPAR gamma	-	0.6898	68.98%
Honey bee toxicity	-	0.7779	77.79%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9885	98.85%

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	98.95%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.57%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.81%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.18%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.88%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.61%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.36%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.85%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.72%	93.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.49%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.46%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.39%	99.17%

Plants that contains it

• Xanthium spinosum

Cross-Links

• PubChem: 12310003
• LOTUS: LTS0206979
• wikiData: Q104998306