1-[3-[[(6S)-5-acetyl-2,4,6-trihydroxy-3,3-dimethylcyclohexa-1,4-dien-1-yl]methyl]-2,4,6-trihydroxy-5-methylphenyl]butan-1-one

Details

• Internal ID: 8feb9b29-2f24-4431-8909-e4396e667987
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-[3-[[(6S)-5-acetyl-2,4,6-trihydroxy-3,3-dimethylcyclohexa-1,4-dien-1-yl]methyl]-2,4,6-trihydroxy-5-methylphenyl]butan-1-one
• SMILES (Canonical): CCCC(=O)C1=C(C(=C(C(=C1O)CC2=C(C(C(=C(C2O)C(=O)C)O)(C)C)O)O)C)O
• SMILES (Isomeric): CCCC(=O)C1=C(C(=C(C(=C1O)CC2=C(C(C(=C([C@H]2O)C(=O)C)O)(C)C)O)O)C)O
• InChI: InChI=1S/C22H28O8/c1-6-7-13(24)15-17(26)9(2)16(25)11(18(15)27)8-12-19(28)14(10(3)23)21(30)22(4,5)20(12)29/h19,25-30H,6-8H2,1-5H3/t19-/m0/s1
• InChI Key: QBTDHAKBGQYTFR-IBGZPJMESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.17841785 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	-	0.5566	55.66%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8433	84.33%
OATP2B1 inhibitior	-	0.5748	57.48%
OATP1B1 inhibitior	+	0.7072	70.72%
OATP1B3 inhibitior	+	0.9009	90.09%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5325	53.25%
P-glycoprotein inhibitior	-	0.7507	75.07%
P-glycoprotein substrate	-	0.6309	63.09%
CYP3A4 substrate	+	0.5855	58.55%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8351	83.51%
CYP3A4 inhibition	+	0.5074	50.74%
CYP2C9 inhibition	+	0.7327	73.27%
CYP2C19 inhibition	+	0.6645	66.45%
CYP2D6 inhibition	-	0.7989	79.89%
CYP1A2 inhibition	+	0.5589	55.89%
CYP2C8 inhibition	-	0.6337	63.37%
CYP inhibitory promiscuity	+	0.7062	70.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8477	84.77%
Carcinogenicity (trinary)	Non-required	0.6564	65.64%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.4837	48.37%
Skin irritation	-	0.7249	72.49%
Skin corrosion	-	0.9083	90.83%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4272	42.72%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5051	50.51%
skin sensitisation	-	0.5282	52.82%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6888	68.88%
Acute Oral Toxicity (c)	III	0.6087	60.87%
Estrogen receptor binding	+	0.8301	83.01%
Androgen receptor binding	-	0.6499	64.99%
Thyroid receptor binding	+	0.5820	58.20%
Glucocorticoid receptor binding	+	0.7421	74.21%
Aromatase binding	+	0.5933	59.33%
PPAR gamma	+	0.6754	67.54%
Honey bee toxicity	-	0.8625	86.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5451	54.51%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.38%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.41%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.85%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.68%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.40%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.88%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.12%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.17%	94.73%

Plants that contains it

• Dryopteris sieboldii

Cross-Links

• PubChem: 163017897
• LOTUS: LTS0192393
• wikiData: Q105217993