(4R)-4-hydroxy-4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one

Details

• Internal ID: ed4088ba-9f07-49d5-8b1f-80265a95a1f3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4R)-4-hydroxy-4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one
• SMILES (Canonical): CC1(CCCC1(C)C2=CC(C=CC2=O)(C)O)C
• SMILES (Isomeric): C[C@@]1(CCCC1(C)C)C2=C[C@](C=CC2=O)(C)O
• InChI: InChI=1S/C15H22O2/c1-13(2)7-5-8-15(13,4)11-10-14(3,17)9-6-12(11)16/h6,9-10,17H,5,7-8H2,1-4H3/t14-,15-/m1/s1
• InChI Key: IAHVMQAYDBMMQB-HUUCEWRRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 2
• 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	+	0.9971	99.71%
Caco-2	+	0.9399	93.99%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7458	74.58%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9224	92.24%
OATP1B3 inhibitior	+	0.9081	90.81%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7727	77.27%
P-glycoprotein inhibitior	-	0.9639	96.39%
P-glycoprotein substrate	-	0.9238	92.38%
CYP3A4 substrate	+	0.5087	50.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	-	0.8562	85.62%
CYP2C9 inhibition	-	0.8560	85.60%
CYP2C19 inhibition	-	0.8560	85.60%
CYP2D6 inhibition	-	0.9247	92.47%
CYP1A2 inhibition	-	0.7568	75.68%
CYP2C8 inhibition	-	0.9710	97.10%
CYP inhibitory promiscuity	-	0.7460	74.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8828	88.28%
Carcinogenicity (trinary)	Non-required	0.5541	55.41%
Eye corrosion	-	0.9703	97.03%
Eye irritation	+	0.6905	69.05%
Skin irritation	+	0.7175	71.75%
Skin corrosion	-	0.9705	97.05%
Ames mutagenesis	-	0.5424	54.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.7907	79.07%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.5889	58.89%
skin sensitisation	+	0.7391	73.91%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.4806	48.06%
Acute Oral Toxicity (c)	III	0.7456	74.56%
Estrogen receptor binding	-	0.8047	80.47%
Androgen receptor binding	-	0.5500	55.00%
Thyroid receptor binding	-	0.5592	55.92%
Glucocorticoid receptor binding	-	0.6941	69.41%
Aromatase binding	-	0.6765	67.65%
PPAR gamma	-	0.8299	82.99%
Honey bee toxicity	-	0.9656	96.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9833	98.33%

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	92.81%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.78%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.41%	82.69%
CHEMBL4208	P20618	Proteasome component C5	88.61%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.13%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	84.97%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.65%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.41%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.62%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.33%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	81.64%	94.75%

Plants that contains it

• Cinnamomum philippinense
• Herbertus sakuraii

Cross-Links

• PubChem: 15545712
• NPASS: NPC114401
• LOTUS: LTS0164333
• wikiData: Q105036114