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

Details

• Internal ID: f0986f96-2863-4b94-82d0-6823f5e2f6a6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (3R,4S,5R)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3-(hydroxymethyl)-3,5-dimethylcyclohexan-1-one
• SMILES (Canonical): CC1CC(=O)CC(C1(C=CC(C)O)O)(C)CO
• SMILES (Isomeric): C[C@@H]1CC(=O)C[C@]([C@]1(/C=C/[C@@H](C)O)O)(C)CO
• InChI: InChI=1S/C13H22O4/c1-9-6-11(16)7-12(3,8-14)13(9,17)5-4-10(2)15/h4-5,9-10,14-15,17H,6-8H2,1-3H3/b5-4+/t9-,10-,12-,13-/m1/s1
• InChI Key: RLKZNMMKYFJAPM-UVJNOFBYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O₄
• Molecular Weight: 242.31 g/mol
• Exact Mass: 242.15180918 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.65
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9527	95.27%
Caco-2	+	0.5362	53.62%
Blood Brain Barrier	+	0.6385	63.85%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8013	80.13%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.9221	92.21%
OATP1B3 inhibitior	+	0.9379	93.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6974	69.74%
P-glycoprotein inhibitior	-	0.9652	96.52%
P-glycoprotein substrate	-	0.8538	85.38%
CYP3A4 substrate	+	0.5093	50.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8480	84.80%
CYP3A4 inhibition	-	0.7018	70.18%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	-	0.8680	86.80%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.8170	81.70%
CYP2C8 inhibition	-	0.9648	96.48%
CYP inhibitory promiscuity	-	0.9252	92.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8250	82.50%
Carcinogenicity (trinary)	Non-required	0.6729	67.29%
Eye corrosion	-	0.9770	97.70%
Eye irritation	-	0.7116	71.16%
Skin irritation	-	0.8143	81.43%
Skin corrosion	-	0.9771	97.71%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7818	78.18%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5058	50.58%
skin sensitisation	-	0.6339	63.39%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	+	0.4564	45.64%
Acute Oral Toxicity (c)	III	0.7267	72.67%
Estrogen receptor binding	-	0.8631	86.31%
Androgen receptor binding	-	0.6654	66.54%
Thyroid receptor binding	-	0.5693	56.93%
Glucocorticoid receptor binding	-	0.5067	50.67%
Aromatase binding	-	0.6764	67.64%
PPAR gamma	-	0.7347	73.47%
Honey bee toxicity	-	0.8667	86.67%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.7998	79.98%

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	96.10%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.13%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.44%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.34%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.08%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.32%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	87.70%	98.03%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.56%	96.47%
CHEMBL1937	Q92769	Histone deacetylase 2	82.38%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.00%	97.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.82%	89.34%
CHEMBL2996	Q05655	Protein kinase C delta	80.12%	97.79%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 101362067
• LOTUS: LTS0005084
• wikiData: Q105240222