(3aS,5S,8S,8aR,9aR)-5-hydroperoxy-8-hydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 5a4c664c-7efc-4167-ac74-84178bca9315
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aS,5S,8S,8aR,9aR)-5-hydroperoxy-8-hydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1(CC=C2C1CC3C(CC2(C)OO)OC(=O)C3=C)O
• SMILES (Isomeric): C[C@@]1(CC=C2[C@H]1C[C@H]3[C@H](C[C@]2(C)OO)OC(=O)C3=C)O
• InChI: InChI=1S/C15H20O5/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,20-18)7-12(9)19-13(8)16/h4,9,11-12,17-18H,1,5-7H2,2-3H3/t9-,11-,12+,14+,15+/m1/s1
• InChI Key: LTPWXJPRGRSAIO-FWTMIXAASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.82
• 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	+	0.9851	98.51%
Caco-2	+	0.5805	58.05%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5502	55.02%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.8929	89.29%
OATP1B3 inhibitior	+	0.9252	92.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9340	93.40%
P-glycoprotein inhibitior	-	0.9187	91.87%
P-glycoprotein substrate	-	0.8244	82.44%
CYP3A4 substrate	+	0.6139	61.39%
CYP2C9 substrate	-	0.7908	79.08%
CYP2D6 substrate	-	0.8533	85.33%
CYP3A4 inhibition	-	0.6651	66.51%
CYP2C9 inhibition	-	0.7736	77.36%
CYP2C19 inhibition	-	0.7782	77.82%
CYP2D6 inhibition	-	0.9313	93.13%
CYP1A2 inhibition	-	0.5645	56.45%
CYP2C8 inhibition	-	0.6628	66.28%
CYP inhibitory promiscuity	-	0.9222	92.22%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5384	53.84%
Eye corrosion	-	0.9753	97.53%
Eye irritation	-	0.8922	89.22%
Skin irritation	-	0.6160	61.60%
Skin corrosion	-	0.8945	89.45%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6106	61.06%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.8074	80.74%
skin sensitisation	-	0.7540	75.40%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5821	58.21%
Acute Oral Toxicity (c)	III	0.3502	35.02%
Estrogen receptor binding	+	0.7095	70.95%
Androgen receptor binding	+	0.6129	61.29%
Thyroid receptor binding	+	0.7093	70.93%
Glucocorticoid receptor binding	+	0.7099	70.99%
Aromatase binding	-	0.5344	53.44%
PPAR gamma	+	0.5460	54.60%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	95.69%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	94.22%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.87%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.78%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.34%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.23%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.19%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.63%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.73%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	80.89%	91.49%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 122206365
• LOTUS: LTS0019874
• wikiData: Q105157087