(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1S,2S,3S)-1,2,3-trihydroxybutyl]cyclohex-2-en-1-one

Details

• Internal ID: 6dcae4cc-03eb-4203-a658-68068d90ae90
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4S)-4-hydroxy-3,5,5-trimethyl-4-[(1S,2S,3S)-1,2,3-trihydroxybutyl]cyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1(C(C(C(C)O)O)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@]1([C@H]([C@H]([C@H](C)O)O)O)O)(C)C
• InChI: InChI=1S/C13H22O5/c1-7-5-9(15)6-12(3,4)13(7,18)11(17)10(16)8(2)14/h5,8,10-11,14,16-18H,6H2,1-4H3/t8-,10-,11-,13-/m0/s1
• InChI Key: OGBUVKKETBQQGV-DJFWLOJKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O₅
• Molecular Weight: 258.31 g/mol
• Exact Mass: 258.14672380 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9171	91.71%
Caco-2	-	0.5869	58.69%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7759	77.59%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.9456	94.56%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7031	70.31%
P-glycoprotein inhibitior	-	0.9526	95.26%
P-glycoprotein substrate	-	0.9531	95.31%
CYP3A4 substrate	+	0.5302	53.02%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8734	87.34%
CYP3A4 inhibition	-	0.7833	78.33%
CYP2C9 inhibition	-	0.7854	78.54%
CYP2C19 inhibition	-	0.8127	81.27%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.8200	82.00%
CYP2C8 inhibition	-	0.9863	98.63%
CYP inhibitory promiscuity	-	0.8653	86.53%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9323	93.23%
Carcinogenicity (trinary)	Non-required	0.5571	55.71%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.6223	62.23%
Skin corrosion	-	0.9110	91.10%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8022	80.22%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5585	55.85%
skin sensitisation	+	0.5535	55.35%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5744	57.44%
Acute Oral Toxicity (c)	III	0.5966	59.66%
Estrogen receptor binding	-	0.8027	80.27%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5278	52.78%
Glucocorticoid receptor binding	-	0.5807	58.07%
Aromatase binding	-	0.6851	68.51%
PPAR gamma	-	0.7064	70.64%
Honey bee toxicity	-	0.9154	91.54%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.9091	90.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.43%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.83%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.39%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.86%	97.25%
CHEMBL4208	P20618	Proteasome component C5	90.95%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.16%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.23%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.44%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.05%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.19%	90.24%
CHEMBL1937	Q92769	Histone deacetylase 2	83.50%	94.75%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.54%	85.94%

Plants that contains it

• Angelica keiskei

Cross-Links

• PubChem: 162866524
• LOTUS: LTS0005684
• wikiData: Q105191526