(3R,3aS,7R,9S,10Z,11aS)-7-hydroperoxy-9-hydroxy-3,10-dimethyl-6-methylidene-3,3a,4,5,7,8,9,11a-octahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 95192b1a-177a-4c55-a068-62eaf7bc6c69
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3R,3aS,7R,9S,10Z,11aS)-7-hydroperoxy-9-hydroxy-3,10-dimethyl-6-methylidene-3,3a,4,5,7,8,9,11a-octahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=C)C(CC(C(=CC2OC1=O)C)O)OO
• SMILES (Isomeric): C[C@@H]1[C@@H]2CCC(=C)[C@@H](C[C@@H](/C(=C\[C@H]2OC1=O)/C)O)OO
• InChI: InChI=1S/C15H22O5/c1-8-4-5-11-10(3)15(17)19-14(11)6-9(2)12(16)7-13(8)20-18/h6,10-14,16,18H,1,4-5,7H2,2-3H3/b9-6-/t10-,11+,12+,13-,14-/m1/s1
• InChI Key: YNUULXDMAGEJIR-VYPTUBAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.07
• 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	+	0.9695	96.95%
Caco-2	+	0.5239	52.39%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6450	64.50%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8996	89.96%
OATP1B3 inhibitior	+	0.9271	92.71%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.9407	94.07%
P-glycoprotein inhibitior	-	0.8874	88.74%
P-glycoprotein substrate	-	0.7696	76.96%
CYP3A4 substrate	+	0.5922	59.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8336	83.36%
CYP3A4 inhibition	-	0.6973	69.73%
CYP2C9 inhibition	-	0.8594	85.94%
CYP2C19 inhibition	-	0.7671	76.71%
CYP2D6 inhibition	-	0.9042	90.42%
CYP1A2 inhibition	-	0.5316	53.16%
CYP2C8 inhibition	-	0.8477	84.77%
CYP inhibitory promiscuity	-	0.8721	87.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9025	90.25%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9680	96.80%
Eye irritation	-	0.8984	89.84%
Skin irritation	-	0.6570	65.70%
Skin corrosion	-	0.9004	90.04%
Ames mutagenesis	-	0.6308	63.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.5855	58.55%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.7912	79.12%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7410	74.10%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6633	66.33%
Acute Oral Toxicity (c)	III	0.3502	35.02%
Estrogen receptor binding	+	0.6257	62.57%
Androgen receptor binding	-	0.6107	61.07%
Thyroid receptor binding	+	0.5620	56.20%
Glucocorticoid receptor binding	+	0.7681	76.81%
Aromatase binding	-	0.5676	56.76%
PPAR gamma	-	0.6327	63.27%
Honey bee toxicity	-	0.7775	77.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9775	97.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.25%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.33%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.79%	97.09%
CHEMBL1871	P10275	Androgen Receptor	86.16%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.97%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.20%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.33%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.71%	93.04%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.08%	94.80%
CHEMBL2581	P07339	Cathepsin D	80.95%	98.95%

Plants that contains it

• Chrysanthemum lavandulifolium

Cross-Links

• PubChem: 21726161
• LOTUS: LTS0243716
• wikiData: Q105351121