8-Acetyl-6-butanoyl-5,7-dihydroxy-4-phenylchromen-2-one

Details

• Internal ID: f922f853-9e85-4f02-92e7-8629780dddf2
• Taxonomy: Phenylpropanoids and polyketides > Neoflavonoids > Neoflavones
• IUPAC Name: 8-acetyl-6-butanoyl-5,7-dihydroxy-4-phenylchromen-2-one
• SMILES (Canonical): CCCC(=O)C1=C(C(=C2C(=C1O)C(=CC(=O)O2)C3=CC=CC=C3)C(=O)C)O
• SMILES (Isomeric): CCCC(=O)C1=C(C(=C2C(=C1O)C(=CC(=O)O2)C3=CC=CC=C3)C(=O)C)O
• InChI: InChI=1S/C21H18O6/c1-3-7-14(23)18-19(25)16(11(2)22)21-17(20(18)26)13(10-15(24)27-21)12-8-5-4-6-9-12/h4-6,8-10,25-26H,3,7H2,1-2H3
• InChI Key: CWYKFYFKUYOIRI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₆
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.11033829 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.06
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• InChI=1/C21H18O6/c1-3-7-14(23)18-19(25)16(11(2)22)21-17(20(18)26)13(10-15(24)27-21)12-8-5-4-6-9-12/h4-6,8-10,25-26H,3,7H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7731	77.31%
Caco-2	+	0.6466	64.66%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7331	73.31%
OATP2B1 inhibitior	-	0.5841	58.41%
OATP1B1 inhibitior	+	0.8162	81.62%
OATP1B3 inhibitior	+	0.9227	92.27%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6573	65.73%
P-glycoprotein inhibitior	-	0.4604	46.04%
P-glycoprotein substrate	-	0.7173	71.73%
CYP3A4 substrate	-	0.5206	52.06%
CYP2C9 substrate	+	0.8643	86.43%
CYP2D6 substrate	-	0.8660	86.60%
CYP3A4 inhibition	-	0.5599	55.99%
CYP2C9 inhibition	+	0.5834	58.34%
CYP2C19 inhibition	-	0.7593	75.93%
CYP2D6 inhibition	-	0.8995	89.95%
CYP1A2 inhibition	-	0.6526	65.26%
CYP2C8 inhibition	+	0.6928	69.28%
CYP inhibitory promiscuity	-	0.6209	62.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7031	70.31%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.6932	69.32%
Skin irritation	-	0.7789	77.89%
Skin corrosion	-	0.8920	89.20%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7039	70.39%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.9011	90.11%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7552	75.52%
Acute Oral Toxicity (c)	I	0.4881	48.81%
Estrogen receptor binding	+	0.7315	73.15%
Androgen receptor binding	+	0.7593	75.93%
Thyroid receptor binding	-	0.6670	66.70%
Glucocorticoid receptor binding	+	0.7379	73.79%
Aromatase binding	+	0.5309	53.09%
PPAR gamma	+	0.8458	84.58%
Honey bee toxicity	-	0.9305	93.05%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9751	97.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.91%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.90%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.06%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.47%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.86%	99.23%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.60%	92.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.53%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.49%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.73%	94.73%

Plants that contains it

• Kayea racemosa

Cross-Links

• PubChem: 15407040
• LOTUS: LTS0106493
• wikiData: Q104971677