(4R)-4-hydroxy-4-[(3S)-3-hydroxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one

Details

• Internal ID: 28b75fea-3c74-4cb8-98e9-bce1260ca5d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4R)-4-hydroxy-4-[(3S)-3-hydroxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1(CCC(C)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@@]1(CC[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/h7,10,14,16H,5-6,8H2,1-4H3/t10-,13-/m0/s1
• InChI Key: CWOFGGNDZOPNFG-GWCFXTLKSA-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: 0.80
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.8017	80.17%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8494	84.94%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.9257	92.57%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.7448	74.48%
P-glycoprotein inhibitior	-	0.9779	97.79%
P-glycoprotein substrate	-	0.8606	86.06%
CYP3A4 substrate	+	0.5215	52.15%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.7289	72.89%
CYP2C9 inhibition	-	0.8817	88.17%
CYP2C19 inhibition	-	0.9281	92.81%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	-	0.9405	94.05%
CYP2C8 inhibition	-	0.9922	99.22%
CYP inhibitory promiscuity	-	0.8906	89.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8728	87.28%
Carcinogenicity (trinary)	Non-required	0.6272	62.72%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.5526	55.26%
Skin irritation	+	0.4900	49.00%
Skin corrosion	-	0.9837	98.37%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8316	83.16%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	+	0.7857	78.57%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5787	57.87%
Acute Oral Toxicity (c)	III	0.6476	64.76%
Estrogen receptor binding	-	0.9271	92.71%
Androgen receptor binding	-	0.5937	59.37%
Thyroid receptor binding	-	0.7069	70.69%
Glucocorticoid receptor binding	-	0.5689	56.89%
Aromatase binding	-	0.8415	84.15%
PPAR gamma	-	0.8438	84.38%
Honey bee toxicity	-	0.9470	94.70%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9797	97.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.22%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.97%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.72%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.22%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.05%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.63%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.98%	86.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.64%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.61%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.64%	90.00%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Casearia sylvestris
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scorodocarpus borneensis
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 25755221
• NPASS: NPC81870
• LOTUS: LTS0269458
• wikiData: Q104400537