(3aR,5aR,8R,8aS)-5a-hydroperoxy-8-hydroxy-1,5-dimethylidene-3a,4,6,7,8,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 769c7de7-9d17-4b61-9cf5-a9ecc3345a2f
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,5aR,8R,8aS)-5a-hydroperoxy-8-hydroxy-1,5-dimethylidene-3a,4,6,7,8,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one
• InChI: InChI=1S/C14H18O5/c1-7-5-12-9(8(2)13(16)18-12)6-10-11(15)3-4-14(7,10)19-17/h9-12,15,17H,1-6H2/t9?,10-,11+,12+,14-/m0/s1
• InChI Key: ZKGFAIXNJVVISV-KJAYNUCNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.29 g/mol
• Exact Mass: 266.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9455	94.55%
Caco-2	-	0.7130	71.30%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6257	62.57%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.8914	89.14%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.9490	94.90%
P-glycoprotein inhibitior	-	0.9454	94.54%
P-glycoprotein substrate	-	0.7942	79.42%
CYP3A4 substrate	+	0.6361	63.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7991	79.91%
CYP3A4 inhibition	-	0.8527	85.27%
CYP2C9 inhibition	-	0.8181	81.81%
CYP2C19 inhibition	-	0.7077	70.77%
CYP2D6 inhibition	-	0.9049	90.49%
CYP1A2 inhibition	-	0.7020	70.20%
CYP2C8 inhibition	-	0.7637	76.37%
CYP inhibitory promiscuity	-	0.9085	90.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9125	91.25%
Carcinogenicity (trinary)	Non-required	0.5334	53.34%
Eye corrosion	-	0.9542	95.42%
Eye irritation	-	0.6940	69.40%
Skin irritation	-	0.6953	69.53%
Skin corrosion	-	0.8735	87.35%
Ames mutagenesis	-	0.6637	66.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6591	65.91%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.7828	78.28%
skin sensitisation	-	0.7849	78.49%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7170	71.70%
Acute Oral Toxicity (c)	III	0.4166	41.66%
Estrogen receptor binding	+	0.8176	81.76%
Androgen receptor binding	+	0.5881	58.81%
Thyroid receptor binding	+	0.5810	58.10%
Glucocorticoid receptor binding	+	0.8893	88.93%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6049	60.49%
Honey bee toxicity	-	0.6963	69.63%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9378	93.78%

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	96.55%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.24%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.23%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.58%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	88.00%	98.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.37%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.89%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.94%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.83%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.59%	93.03%
CHEMBL1902	P62942	FK506-binding protein 1A	82.42%	97.05%
CHEMBL3572	P11597	Cholesteryl ester transfer protein	81.69%	92.67%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.40%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.35%	100.00%
CHEMBL217	P14416	Dopamine D2 receptor	80.93%	95.62%

Plants that contains it

• Pluchea dioscoridis

Cross-Links

• PubChem: 162816858
• LOTUS: LTS0081316
• wikiData: Q105378442