(4Z,6S,9R,9aS)-9a-hydroperoxy-2,2,5,9-tetramethyl-6,7,8,9-tetrahydro-1H-cyclopenta[8]annulen-6-ol

Details

• Internal ID: 7f8e1bad-7692-41e2-8240-de629466535a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4Z,6S,9R,9aS)-9a-hydroperoxy-2,2,5,9-tetramethyl-6,7,8,9-tetrahydro-1H-cyclopenta[8]annulen-6-ol
• SMILES (Canonical): CC1CCC(C(=CC2=CC(CC12OO)(C)C)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@@H](/C(=C\C2=CC(C[C@]12OO)(C)C)/C)O
• InChI: InChI=1S/C15H24O3/c1-10-7-12-8-14(3,4)9-15(12,18-17)11(2)5-6-13(10)16/h7-8,11,13,16-17H,5-6,9H2,1-4H3/b10-7-/t11-,13+,15+/m1/s1
• InChI Key: JXXGQPLNOPZHMH-GUSBQHCYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 3
• 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	+	0.9925	99.25%
Caco-2	+	0.8221	82.21%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6106	61.06%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9237	92.37%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9133	91.33%
P-glycoprotein inhibitior	-	0.9556	95.56%
P-glycoprotein substrate	-	0.7130	71.30%
CYP3A4 substrate	+	0.5732	57.32%
CYP2C9 substrate	-	0.6844	68.44%
CYP2D6 substrate	-	0.7496	74.96%
CYP3A4 inhibition	-	0.7852	78.52%
CYP2C9 inhibition	-	0.7839	78.39%
CYP2C19 inhibition	-	0.7663	76.63%
CYP2D6 inhibition	-	0.9274	92.74%
CYP1A2 inhibition	-	0.7255	72.55%
CYP2C8 inhibition	-	0.7784	77.84%
CYP inhibitory promiscuity	-	0.7590	75.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.5417	54.17%
Eye corrosion	-	0.9774	97.74%
Eye irritation	-	0.9365	93.65%
Skin irritation	+	0.5139	51.39%
Skin corrosion	-	0.9088	90.88%
Ames mutagenesis	+	0.5092	50.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.3775	37.75%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5466	54.66%
skin sensitisation	-	0.6136	61.36%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5571	55.71%
Acute Oral Toxicity (c)	III	0.5425	54.25%
Estrogen receptor binding	-	0.8566	85.66%
Androgen receptor binding	-	0.5169	51.69%
Thyroid receptor binding	+	0.6027	60.27%
Glucocorticoid receptor binding	-	0.5962	59.62%
Aromatase binding	-	0.7525	75.25%
PPAR gamma	-	0.6993	69.93%
Honey bee toxicity	-	0.9055	90.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.53%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.43%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.13%	95.89%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.43%	92.68%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.13%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.80%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.06%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	81.26%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.01%	100.00%
CHEMBL1871	P10275	Androgen Receptor	80.93%	96.43%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 73353713
• LOTUS: LTS0250464
• wikiData: Q105136846