(4S,5S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,3,5-trimethylcyclohexan-1-one

Details

• Internal ID: cb348425-01de-48ee-bc49-b48f90059cd1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4S,5S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,3,5-trimethylcyclohexan-1-one
• SMILES (Canonical): CC1CC(=O)CC(C1(C=CC(C)O)O)(C)C
• SMILES (Isomeric): C[C@H]1CC(=O)CC([C@]1(/C=C/[C@@H](C)O)O)(C)C
• InChI: InChI=1S/C13H22O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-6,9-10,14,16H,7-8H2,1-4H3/b6-5+/t9-,10+,13+/m0/s1
• InChI Key: IHDJYDVWNNFPHR-RMQMSNBUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.31 g/mol
• Exact Mass: 226.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.6673	66.73%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8793	87.93%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9318	93.18%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7740	77.40%
P-glycoprotein inhibitior	-	0.9657	96.57%
P-glycoprotein substrate	-	0.8285	82.85%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8367	83.67%
CYP3A4 inhibition	-	0.8249	82.49%
CYP2C9 inhibition	-	0.8564	85.64%
CYP2C19 inhibition	-	0.8886	88.86%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.9225	92.25%
CYP2C8 inhibition	-	0.9865	98.65%
CYP inhibitory promiscuity	-	0.9347	93.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7663	76.63%
Carcinogenicity (trinary)	Non-required	0.5668	56.68%
Eye corrosion	-	0.9103	91.03%
Eye irritation	+	0.5883	58.83%
Skin irritation	-	0.5598	55.98%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8057	80.57%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5592	55.92%
skin sensitisation	+	0.8241	82.41%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6208	62.08%
Acute Oral Toxicity (c)	III	0.7804	78.04%
Estrogen receptor binding	-	0.8786	87.86%
Androgen receptor binding	-	0.7513	75.13%
Thyroid receptor binding	-	0.5899	58.99%
Glucocorticoid receptor binding	-	0.5754	57.54%
Aromatase binding	-	0.7314	73.14%
PPAR gamma	-	0.7928	79.28%
Honey bee toxicity	-	0.8675	86.75%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9364	93.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.68%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.33%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.78%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.97%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	86.68%	94.75%
CHEMBL299	P17252	Protein kinase C alpha	85.13%	98.03%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.53%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.48%	96.47%

Plants that contains it

• Croton lechleri
• Vitis vinifera

Cross-Links

• PubChem: 162964206
• LOTUS: LTS0249536
• wikiData: Q105112945