6,7,8-Trihydroxy-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 9c29cf52-c9a5-433b-b9c2-cb9a12f01445
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 5-O-methylated flavonoids
• IUPAC Name: 6,7,8-trihydroxy-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C(=C(C2=C1C(=O)CC(O2)C3=CC=CC=C3)O)O)O
• SMILES (Isomeric): COC1=C(C(=C(C2=C1C(=O)CC(O2)C3=CC=CC=C3)O)O)O
• InChI: InChI=1S/C16H14O6/c1-21-15-11-9(17)7-10(8-5-3-2-4-6-8)22-16(11)14(20)12(18)13(15)19/h2-6,10,18-20H,7H2,1H3
• InChI Key: PKAFYSRHNWFISU-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9096	90.96%
Caco-2	-	0.8365	83.65%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6421	64.21%
OATP2B1 inhibitior	-	0.8647	86.47%
OATP1B1 inhibitior	+	0.8915	89.15%
OATP1B3 inhibitior	+	0.9873	98.73%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8940	89.40%
P-glycoprotein inhibitior	-	0.7833	78.33%
P-glycoprotein substrate	-	0.9368	93.68%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6825	68.25%
CYP3A4 inhibition	+	0.6515	65.15%
CYP2C9 inhibition	-	0.7533	75.33%
CYP2C19 inhibition	-	0.5911	59.11%
CYP2D6 inhibition	-	0.8152	81.52%
CYP1A2 inhibition	+	0.8299	82.99%
CYP2C8 inhibition	-	0.5927	59.27%
CYP inhibitory promiscuity	+	0.5816	58.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6061	60.61%
Eye corrosion	-	0.9827	98.27%
Eye irritation	+	0.6135	61.35%
Skin irritation	-	0.6552	65.52%
Skin corrosion	-	0.9208	92.08%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5878	58.78%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	+	0.5157	51.57%
skin sensitisation	-	0.8950	89.50%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5535	55.35%
Acute Oral Toxicity (c)	III	0.6074	60.74%
Estrogen receptor binding	-	0.4944	49.44%
Androgen receptor binding	-	0.5639	56.39%
Thyroid receptor binding	-	0.5378	53.78%
Glucocorticoid receptor binding	+	0.8329	83.29%
Aromatase binding	-	0.6387	63.87%
PPAR gamma	+	0.6515	65.15%
Honey bee toxicity	-	0.8992	89.92%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7486	74.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.12%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.68%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.15%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.11%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.96%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.99%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.21%	97.09%

Plants that contains it

• Isodon oresbius

Cross-Links

• PubChem: 74819437
• LOTUS: LTS0176629
• wikiData: Q105210262