3-hydroxy-2-methyl-5-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-diene-1,4-dione

Details

• Internal ID: 92e95568-b82a-4a92-b235-7b08e077669e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 3-hydroxy-2-methyl-5-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-diene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C(=CC1=O)C2(CCCC2(C)C)C)O
• SMILES (Isomeric): CC1=C(C(=O)C(=CC1=O)[C@]2(CCCC2(C)C)C)O
• InChI: InChI=1S/C15H20O3/c1-9-11(16)8-10(13(18)12(9)17)15(4)7-5-6-14(15,2)3/h8,17H,5-7H2,1-4H3/t15-/m1/s1
• InChI Key: CJBHXGXJJDLMPE-OAHLLOKOSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 3
• 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	+	0.9942	99.42%
Caco-2	+	0.9523	95.23%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8358	83.58%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8896	88.96%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7699	76.99%
P-glycoprotein inhibitior	-	0.9461	94.61%
P-glycoprotein substrate	-	0.9234	92.34%
CYP3A4 substrate	+	0.5233	52.33%
CYP2C9 substrate	-	0.8080	80.80%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.8828	88.28%
CYP2C9 inhibition	-	0.7559	75.59%
CYP2C19 inhibition	-	0.8769	87.69%
CYP2D6 inhibition	-	0.9178	91.78%
CYP1A2 inhibition	-	0.7808	78.08%
CYP2C8 inhibition	-	0.9633	96.33%
CYP inhibitory promiscuity	-	0.8751	87.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8550	85.50%
Carcinogenicity (trinary)	Non-required	0.5257	52.57%
Eye corrosion	-	0.9775	97.75%
Eye irritation	+	0.7145	71.45%
Skin irritation	+	0.5962	59.62%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6127	61.27%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6421	64.21%
skin sensitisation	+	0.5545	55.45%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.4494	44.94%
Acute Oral Toxicity (c)	III	0.6531	65.31%
Estrogen receptor binding	-	0.4787	47.87%
Androgen receptor binding	+	0.6637	66.37%
Thyroid receptor binding	+	0.5557	55.57%
Glucocorticoid receptor binding	-	0.5364	53.64%
Aromatase binding	-	0.5941	59.41%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9322	93.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9881	98.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.02%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.96%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.70%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.60%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	87.74%	94.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.86%	82.69%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.81%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.99%	89.00%
CHEMBL230	P35354	Cyclooxygenase-2	80.98%	89.63%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.97%	100.00%

Plants that contains it

• Lejeunea aquatica

Cross-Links

• PubChem: 102425910
• LOTUS: LTS0227585
• wikiData: Q104375158