(2S,3S)-3,5,7-trihydroxy-6-methyl-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: c255033f-95c1-4aa4-b496-f0b682f39c45
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2S,3S)-3,5,7-trihydroxy-6-methyl-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1=C(C2=C(C=C1O)OC(C(C2=O)O)C3=CC=CC=C3)O
• SMILES (Isomeric): CC1=C(C2=C(C=C1O)O[C@H]([C@@H](C2=O)O)C3=CC=CC=C3)O
• InChI: InChI=1S/C16H14O5/c1-8-10(17)7-11-12(13(8)18)14(19)15(20)16(21-11)9-5-3-2-4-6-9/h2-7,15-18,20H,1H3/t15-,16+/m1/s1
• InChI Key: VAJGHLOBFXQACD-CVEARBPZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9584	95.84%
Caco-2	-	0.8099	80.99%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6875	68.75%
OATP2B1 inhibitior	-	0.7185	71.85%
OATP1B1 inhibitior	+	0.8706	87.06%
OATP1B3 inhibitior	+	0.7919	79.19%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8167	81.67%
P-glycoprotein inhibitior	-	0.6856	68.56%
P-glycoprotein substrate	-	0.9520	95.20%
CYP3A4 substrate	-	0.5402	54.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8042	80.42%
CYP3A4 inhibition	+	0.6854	68.54%
CYP2C9 inhibition	+	0.8171	81.71%
CYP2C19 inhibition	+	0.5859	58.59%
CYP2D6 inhibition	-	0.9043	90.43%
CYP1A2 inhibition	+	0.9502	95.02%
CYP2C8 inhibition	-	0.6480	64.80%
CYP inhibitory promiscuity	+	0.7850	78.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6793	67.93%
Eye corrosion	-	0.9882	98.82%
Eye irritation	+	0.8089	80.89%
Skin irritation	+	0.5397	53.97%
Skin corrosion	-	0.9023	90.23%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7320	73.20%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.6158	61.58%
skin sensitisation	-	0.8434	84.34%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5739	57.39%
Acute Oral Toxicity (c)	III	0.6137	61.37%
Estrogen receptor binding	-	0.5135	51.35%
Androgen receptor binding	+	0.6237	62.37%
Thyroid receptor binding	+	0.6169	61.69%
Glucocorticoid receptor binding	+	0.6925	69.25%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7217	72.17%
Honey bee toxicity	-	0.9537	95.37%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9001	90.01%

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	97.10%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.31%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.56%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.91%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.82%	99.23%
CHEMBL2581	P07339	Cathepsin D	91.47%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.58%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.64%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.82%	99.15%

Plants that contains it

• Isodon rubescens
• Pinus strobus

Cross-Links

• PubChem: 162978751
• LOTUS: LTS0267085
• wikiData: Q105206781