(3S,3aS,9aR,9bR)-9a-hydroxy-3,6,9-trimethyl-3a,4,5,9b-tetrahydro-3H-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 5802185b-6786-4ac2-8414-d9c143a09798
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,3aS,9aR,9bR)-9a-hydroxy-3,6,9-trimethyl-3a,4,5,9b-tetrahydro-3H-azuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1C2CCC(=C3C(=O)C=C(C3(C2OC1=O)O)C)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CCC(=C3C(=O)C=C([C@@]3([C@@H]2OC1=O)O)C)C
• InChI: InChI=1S/C15H18O4/c1-7-4-5-10-9(3)14(17)19-13(10)15(18)8(2)6-11(16)12(7)15/h6,9-10,13,18H,4-5H2,1-3H3/t9-,10-,13+,15+/m0/s1
• InChI Key: HRDKPHGABXKGQR-UOJCWERNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9726	97.26%
Caco-2	+	0.8005	80.05%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5949	59.49%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9337	93.37%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	-	0.8882	88.82%
P-glycoprotein inhibitior	-	0.8942	89.42%
P-glycoprotein substrate	-	0.7909	79.09%
CYP3A4 substrate	+	0.5927	59.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9043	90.43%
CYP3A4 inhibition	-	0.8681	86.81%
CYP2C9 inhibition	-	0.7786	77.86%
CYP2C19 inhibition	-	0.8394	83.94%
CYP2D6 inhibition	-	0.9249	92.49%
CYP1A2 inhibition	+	0.8449	84.49%
CYP2C8 inhibition	-	0.9385	93.85%
CYP inhibitory promiscuity	-	0.9273	92.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4050	40.50%
Eye corrosion	-	0.9755	97.55%
Eye irritation	-	0.8764	87.64%
Skin irritation	+	0.5895	58.95%
Skin corrosion	-	0.7893	78.93%
Ames mutagenesis	-	0.8224	82.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.6629	66.29%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.7962	79.62%
skin sensitisation	-	0.7523	75.23%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4155	41.55%
Estrogen receptor binding	-	0.6669	66.69%
Androgen receptor binding	-	0.5253	52.53%
Thyroid receptor binding	-	0.6381	63.81%
Glucocorticoid receptor binding	-	0.5453	54.53%
Aromatase binding	-	0.7978	79.78%
PPAR gamma	-	0.6838	68.38%
Honey bee toxicity	-	0.9325	93.25%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9558	95.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.16%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.29%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.92%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.83%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.25%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.85%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.46%	94.80%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.67%	93.40%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.44%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.35%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.50%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.72%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	82.61%	94.75%

Plants that contains it

• Artemisia gorgonum

Cross-Links

• PubChem: 102027676
• LOTUS: LTS0140851
• wikiData: Q105032592