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

Details

• Internal ID: 6adbbea6-08c5-40dc-92cd-38df8ae4f3e6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,4R,5E,9S,10E,11aS)-9-hydroperoxy-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC(C2C(C=C(C(CC1)OO)C)OC(=O)C2=C)O
• SMILES (Isomeric): C/C/1=C\[C@H]([C@H]2[C@H](/C=C(/[C@H](CC1)OO)\C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O5/c1-8-4-5-12(20-18)9(2)7-13-14(11(16)6-8)10(3)15(17)19-13/h6-7,11-14,16,18H,3-5H2,1-2H3/b8-6+,9-7+/t11-,12+,13+,14+/m1/s1
• InChI Key: DEQKXGXANSEDAD-BSLNNEFRSA-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: 0.70
• Atomic LogP (AlogP): 1.99
• 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	+	0.9594	95.94%
Caco-2	+	0.6751	67.51%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5615	56.15%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9206	92.06%
OATP1B3 inhibitior	+	0.9068	90.68%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8571	85.71%
BSEP inhibitior	-	0.9323	93.23%
P-glycoprotein inhibitior	-	0.8475	84.75%
P-glycoprotein substrate	-	0.9146	91.46%
CYP3A4 substrate	+	0.5562	55.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8297	82.97%
CYP3A4 inhibition	-	0.6628	66.28%
CYP2C9 inhibition	-	0.7974	79.74%
CYP2C19 inhibition	-	0.7484	74.84%
CYP2D6 inhibition	-	0.8947	89.47%
CYP1A2 inhibition	+	0.5782	57.82%
CYP2C8 inhibition	-	0.8014	80.14%
CYP inhibitory promiscuity	-	0.7750	77.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5623	56.23%
Eye corrosion	-	0.9637	96.37%
Eye irritation	-	0.8473	84.73%
Skin irritation	-	0.6356	63.56%
Skin corrosion	-	0.8519	85.19%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6645	66.45%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7652	76.52%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6855	68.55%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5743	57.43%
Acute Oral Toxicity (c)	III	0.3965	39.65%
Estrogen receptor binding	-	0.4774	47.74%
Androgen receptor binding	-	0.6551	65.51%
Thyroid receptor binding	-	0.6331	63.31%
Glucocorticoid receptor binding	-	0.5616	56.16%
Aromatase binding	-	0.6427	64.27%
PPAR gamma	+	0.5494	54.94%
Honey bee toxicity	-	0.7859	78.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9651	96.51%

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	93.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.59%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.62%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.96%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.83%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.51%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.42%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.35%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.73%	97.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.32%	97.33%

Plants that contains it

• Schistostephium crataegifolium

Cross-Links

• PubChem: 163002353
• LOTUS: LTS0221711
• wikiData: Q104977428