[(3aR,4S,9S,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] acetate

Details

• Internal ID: 27cffbdc-cc1b-4701-9be5-90f9c1e7c914
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3aR,4S,9S,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1=C2C=CC(C2C3C(C(C1)OC(=O)C)C(=C)C(=O)O3)(C)O
• SMILES (Isomeric): CC1=C2C=C[C@]([C@@H]2[C@@H]3[C@@H]([C@H](C1)OC(=O)C)C(=C)C(=O)O3)(C)O
• InChI: InChI=1S/C17H20O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,12-15,20H,2,7H2,1,3-4H3/t12-,13+,14-,15-,17-/m0/s1
• InChI Key: ZUVGPNXZXSQDBI-PFFSRIRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.34 g/mol
• Exact Mass: 304.13107373 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	+	0.5539	55.39%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5583	55.83%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9057	90.57%
OATP1B3 inhibitior	+	0.8616	86.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9608	96.08%
P-glycoprotein inhibitior	-	0.7438	74.38%
P-glycoprotein substrate	-	0.7388	73.88%
CYP3A4 substrate	+	0.6335	63.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8998	89.98%
CYP3A4 inhibition	-	0.6434	64.34%
CYP2C9 inhibition	-	0.8322	83.22%
CYP2C19 inhibition	-	0.8841	88.41%
CYP2D6 inhibition	-	0.9628	96.28%
CYP1A2 inhibition	-	0.6001	60.01%
CYP2C8 inhibition	-	0.7075	70.75%
CYP inhibitory promiscuity	-	0.9252	92.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.4156	41.56%
Eye corrosion	-	0.9629	96.29%
Eye irritation	-	0.7439	74.39%
Skin irritation	-	0.5759	57.59%
Skin corrosion	-	0.8919	89.19%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3990	39.90%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.7995	79.95%
skin sensitisation	-	0.6414	64.14%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5479	54.79%
Acute Oral Toxicity (c)	II	0.5274	52.74%
Estrogen receptor binding	-	0.5554	55.54%
Androgen receptor binding	-	0.4934	49.34%
Thyroid receptor binding	+	0.5747	57.47%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7436	74.36%
PPAR gamma	-	0.5133	51.33%
Honey bee toxicity	-	0.7968	79.68%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5150	51.50%
Fish aquatic toxicity	+	0.9626	96.26%

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	96.38%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.68%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.46%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.11%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.94%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.24%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.90%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.65%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.70%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.43%	90.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.24%	94.80%

Plants that contains it

• Rennera eenii

Cross-Links

• PubChem: 163034506
• LOTUS: LTS0008586
• wikiData: Q105384135