(3aR,5R,9E,11aS)-5-hydroperoxy-10-methyl-3,6-dimethylidene-4,5,7,8,11,11a-hexahydro-3aH-cyclodeca[b]furan-2-one

Details

• Internal ID: ca6bf6ce-dac9-4b11-b329-d2609b5a392b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aR,5R,9E,11aS)-5-hydroperoxy-10-methyl-3,6-dimethylidene-4,5,7,8,11,11a-hexahydro-3aH-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CCCC(=C)C(CC2C(C1)OC(=O)C2=C)OO
• SMILES (Isomeric): C/C/1=C\CCC(=C)[C@@H](C[C@H]2[C@H](C1)OC(=O)C2=C)OO
• InChI: InChI=1S/C15H20O4/c1-9-5-4-6-10(2)13(19-17)8-12-11(3)15(16)18-14(12)7-9/h5,12-14,17H,2-4,6-8H2,1H3/b9-5+/t12-,13-,14+/m1/s1
• InChI Key: VJRAEZGZDCGNTL-QGBZXDMCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 4
• 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	+	0.9806	98.06%
Caco-2	+	0.6619	66.19%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5872	58.72%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9250	92.50%
OATP1B3 inhibitior	+	0.9097	90.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.9216	92.16%
P-glycoprotein inhibitior	-	0.9016	90.16%
P-glycoprotein substrate	-	0.9057	90.57%
CYP3A4 substrate	+	0.5413	54.13%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8390	83.90%
CYP3A4 inhibition	-	0.7675	76.75%
CYP2C9 inhibition	-	0.8370	83.70%
CYP2C19 inhibition	-	0.7016	70.16%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	+	0.6477	64.77%
CYP2C8 inhibition	-	0.6570	65.70%
CYP inhibitory promiscuity	-	0.8569	85.69%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6061	60.61%
Eye corrosion	-	0.9555	95.55%
Eye irritation	-	0.7484	74.84%
Skin irritation	-	0.6147	61.47%
Skin corrosion	-	0.9006	90.06%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4623	46.23%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.7380	73.80%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7267	72.67%
Acute Oral Toxicity (c)	III	0.4944	49.44%
Estrogen receptor binding	-	0.5659	56.59%
Androgen receptor binding	-	0.5420	54.20%
Thyroid receptor binding	-	0.5617	56.17%
Glucocorticoid receptor binding	+	0.7021	70.21%
Aromatase binding	-	0.7123	71.23%
PPAR gamma	+	0.5402	54.02%
Honey bee toxicity	-	0.7600	76.00%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9921	99.21%

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	93.13%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.11%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.12%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.96%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.83%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.20%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.57%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.69%	90.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.00%	96.00%

Plants that contains it

• Calea szyszylowiczii

Cross-Links

• PubChem: 163056467
• LOTUS: LTS0237598
• wikiData: Q105287453