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

Details

• Internal ID: 4722f8d0-ee06-4083-bbad-7409e8cfbfd2
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3aR,4S,9aR,9bR)-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1=C2CC=C(C2C3C(C(C1)OC(=O)C)C(=C)C(=O)O3)C
• SMILES (Isomeric): CC1=C2CC=C([C@H]2[C@@H]3[C@@H]([C@H](C1)OC(=O)C)C(=C)C(=O)O3)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/h5,13-16H,3,6-7H2,1-2,4H3/t13-,14+,15+,16+/m0/s1
• InChI Key: YSIJTYIIZIQCSP-ZJIFWQFVSA-N
• Popularity: 1 reference 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: 1.70
• 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	+	0.9928	99.28%
Caco-2	+	0.7555	75.55%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5131	51.31%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9251	92.51%
OATP1B3 inhibitior	+	0.8888	88.88%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9319	93.19%
P-glycoprotein inhibitior	-	0.7670	76.70%
P-glycoprotein substrate	-	0.7961	79.61%
CYP3A4 substrate	+	0.5764	57.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.5818	58.18%
CYP2C9 inhibition	-	0.8303	83.03%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.9555	95.55%
CYP1A2 inhibition	+	0.5668	56.68%
CYP2C8 inhibition	-	0.7525	75.25%
CYP inhibitory promiscuity	-	0.8738	87.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5656	56.56%
Eye corrosion	-	0.9464	94.64%
Eye irritation	-	0.4822	48.22%
Skin irritation	-	0.6061	60.61%
Skin corrosion	-	0.9316	93.16%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.7745	77.45%
skin sensitisation	-	0.7199	71.99%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.8710	87.10%
Acute Oral Toxicity (c)	II	0.4204	42.04%
Estrogen receptor binding	-	0.6034	60.34%
Androgen receptor binding	+	0.5861	58.61%
Thyroid receptor binding	-	0.5623	56.23%
Glucocorticoid receptor binding	+	0.5717	57.17%
Aromatase binding	-	0.7858	78.58%
PPAR gamma	-	0.6252	62.52%
Honey bee toxicity	-	0.6896	68.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.41%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.71%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.53%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.04%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.28%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.40%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	85.34%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.95%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.85%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.58%	93.65%

Plants that contains it

• Hilliardia zuurbergensis

Cross-Links

• PubChem: 162946340
• LOTUS: LTS0262876
• wikiData: Q105359666