(3R)-3abeta,4,5,9balpha-Tetrahydro-4beta-acetoxy-3alpha,6,9-trimethylazuleno[4,5-b]furan-2(3H)-one

Details

• Internal ID: e60a40cc-5b9d-4ee2-8436-4f18bc736077
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3R,3aR,4S,9bS)-3,6,9-trimethyl-2-oxo-3a,4,5,9b-tetrahydro-3H-azuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1C2C(CC(=C3C=CC(=C3C2OC1=O)C)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@@H]2[C@H](CC(=C3C=CC(=C3[C@H]2OC1=O)C)C)OC(=O)C
• InChI: InChI=1S/C17H20O4/c1-8-5-6-12-9(2)7-13(20-11(4)18)15-10(3)17(19)21-16(15)14(8)12/h5-6,10,13,15-16H,7H2,1-4H3/t10-,13+,15-,16-/m1/s1
• InChI Key: XCPJIDFERYSZPG-UCDYDWOKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₄
• Molecular Weight: 288.34 g/mol
• Exact Mass: 288.13615911 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.7346	73.46%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5430	54.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9232	92.32%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6803	68.03%
P-glycoprotein inhibitior	-	0.7257	72.57%
P-glycoprotein substrate	-	0.7955	79.55%
CYP3A4 substrate	+	0.5743	57.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.7916	79.16%
CYP2C9 inhibition	-	0.8490	84.90%
CYP2C19 inhibition	-	0.8358	83.58%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.5365	53.65%
CYP2C8 inhibition	-	0.9023	90.23%
CYP inhibitory promiscuity	-	0.7969	79.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4397	43.97%
Eye corrosion	-	0.9282	92.82%
Eye irritation	-	0.6633	66.33%
Skin irritation	-	0.6633	66.33%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.5028	50.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7269	72.69%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7481	74.81%
skin sensitisation	-	0.7025	70.25%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6111	61.11%
Acute Oral Toxicity (c)	III	0.4159	41.59%
Estrogen receptor binding	-	0.6509	65.09%
Androgen receptor binding	-	0.4853	48.53%
Thyroid receptor binding	-	0.6247	62.47%
Glucocorticoid receptor binding	-	0.6434	64.34%
Aromatase binding	-	0.8050	80.50%
PPAR gamma	-	0.7034	70.34%
Honey bee toxicity	-	0.8599	85.99%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.9492	94.92%

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	94.84%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.12%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.51%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.99%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.87%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.14%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.15%	94.80%

Plants that contains it

• Catha edulis
• Tanacetum annuum

Cross-Links

• PubChem: 14563847
• NPASS: NPC189479
• LOTUS: LTS0025412
• wikiData: Q105325304