[(3S,3aR,4S,9aS,9bR)-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate

Details

• Internal ID: 3bfe4d89-12e3-48a2-9966-a91e3000f6a8
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3S,3aR,4S,9aS,9bR)-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1C2C(CC(=C3C(C2OC1=O)C(=CC3=O)CO)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C3[C@@H]([C@H]2OC1=O)C(=CC3=O)CO)C)OC(=O)C
• InChI: InChI=1S/C17H20O6/c1-7-4-12(22-9(3)19)14-8(2)17(21)23-16(14)15-10(6-18)5-11(20)13(7)15/h5,8,12,14-16,18H,4,6H2,1-3H3/t8-,12-,14+,15-,16-/m0/s1
• InChI Key: QVZHTQXGRRFBCE-IGCQYLLBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 6
• 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	+	0.9865	98.65%
Caco-2	+	0.6805	68.05%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6359	63.59%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.9176	91.76%
MATE1 inhibitior	-	0.7812	78.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7351	73.51%
P-glycoprotein inhibitior	-	0.7604	76.04%
P-glycoprotein substrate	-	0.6816	68.16%
CYP3A4 substrate	+	0.5774	57.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9063	90.63%
CYP3A4 inhibition	-	0.7757	77.57%
CYP2C9 inhibition	-	0.7924	79.24%
CYP2C19 inhibition	-	0.8512	85.12%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.5566	55.66%
CYP2C8 inhibition	-	0.8647	86.47%
CYP inhibitory promiscuity	-	0.8590	85.90%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.5113	51.13%
Eye corrosion	-	0.9661	96.61%
Eye irritation	-	0.7878	78.78%
Skin irritation	-	0.6604	66.04%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.6272	62.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.5774	57.74%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6566	65.66%
skin sensitisation	-	0.7727	77.27%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5894	58.94%
Acute Oral Toxicity (c)	III	0.4841	48.41%
Estrogen receptor binding	-	0.5273	52.73%
Androgen receptor binding	+	0.7004	70.04%
Thyroid receptor binding	-	0.5518	55.18%
Glucocorticoid receptor binding	+	0.5490	54.90%
Aromatase binding	-	0.7807	78.07%
PPAR gamma	-	0.6303	63.03%
Honey bee toxicity	-	0.8327	83.27%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.8544	85.44%

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	94.74%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.47%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.18%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.65%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.13%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.91%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.59%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.64%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.61%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.59%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.22%	97.09%

Plants that contains it

• Lactuca floridana
• Launaea mucronata

Cross-Links

• PubChem: 139077476
• LOTUS: LTS0116974
• wikiData: Q105229019