(2S,3S)-3,5,7-trihydroxy-8-methoxy-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: c992052b-cc72-482b-b057-7002d9271840
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: (2S,3S)-3,5,7-trihydroxy-8-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=C(C2=C1OC(C(C2=O)O)C3=CC=CC=C3)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1O[C@H]([C@@H](C2=O)O)C3=CC=CC=C3)O)O
• InChI: InChI=1S/C16H14O6/c1-21-15-10(18)7-9(17)11-12(19)13(20)14(22-16(11)15)8-5-3-2-4-6-8/h2-7,13-14,17-18,20H,1H3/t13-,14+/m1/s1
• InChI Key: CVICOXSKVBRPGG-KGLIPLIRSA-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: 2.20
• Atomic LogP (AlogP): 1.78
• 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	+	0.9524	95.24%
Caco-2	+	0.4904	49.04%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6494	64.94%
OATP2B1 inhibitior	-	0.7228	72.28%
OATP1B1 inhibitior	+	0.8946	89.46%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7601	76.01%
P-glycoprotein inhibitior	-	0.6036	60.36%
P-glycoprotein substrate	-	0.9514	95.14%
CYP3A4 substrate	-	0.5088	50.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7873	78.73%
CYP3A4 inhibition	+	0.7348	73.48%
CYP2C9 inhibition	+	0.7560	75.60%
CYP2C19 inhibition	+	0.8648	86.48%
CYP2D6 inhibition	-	0.6993	69.93%
CYP1A2 inhibition	+	0.9218	92.18%
CYP2C8 inhibition	-	0.6263	62.63%
CYP inhibitory promiscuity	+	0.8546	85.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6176	61.76%
Eye corrosion	-	0.9767	97.67%
Eye irritation	+	0.6525	65.25%
Skin irritation	-	0.5841	58.41%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6094	60.94%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6322	63.22%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4669	46.69%
Acute Oral Toxicity (c)	III	0.7362	73.62%
Estrogen receptor binding	+	0.5868	58.68%
Androgen receptor binding	-	0.4842	48.42%
Thyroid receptor binding	+	0.6021	60.21%
Glucocorticoid receptor binding	+	0.7281	72.81%
Aromatase binding	-	0.5609	56.09%
PPAR gamma	+	0.5251	52.51%
Honey bee toxicity	-	0.9019	90.19%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8321	83.21%

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	97.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.72%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.34%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.30%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.99%	99.23%
CHEMBL2581	P07339	Cathepsin D	87.72%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.55%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.10%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.43%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	82.19%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.72%	89.00%
CHEMBL2535	P11166	Glucose transporter	80.62%	98.75%

Plants that contains it

• Adenostoma sparsifolium

Cross-Links

• PubChem: 162867101
• LOTUS: LTS0231571
• wikiData: Q104970753