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

Details

• Internal ID: bef7047a-e613-424a-ad48-58c2dd30868a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (2S)-5,7,8-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C(=CC(=C2O)O)O)C3=CC=C(C=C3)O
• SMILES (Isomeric): C1[C@H](OC2=C(C1=O)C(=CC(=C2O)O)O)C3=CC=C(C=C3)O
• InChI: InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)12-6-10(18)13-9(17)5-11(19)14(20)15(13)21-12/h1-5,12,16-17,19-20H,6H2/t12-/m0/s1
• InChI Key: NUNODKNZSZKXGY-LBPRGKRZSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.22
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• LMPK12140667
• 2569-76-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8185	81.85%
Caco-2	-	0.6086	60.86%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5959	59.59%
OATP2B1 inhibitior	-	0.7227	72.27%
OATP1B1 inhibitior	+	0.8760	87.60%
OATP1B3 inhibitior	+	0.9799	97.99%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9027	90.27%
P-glycoprotein inhibitior	-	0.9305	93.05%
P-glycoprotein substrate	-	0.9439	94.39%
CYP3A4 substrate	-	0.5488	54.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7613	76.13%
CYP3A4 inhibition	+	0.7009	70.09%
CYP2C9 inhibition	+	0.5787	57.87%
CYP2C19 inhibition	-	0.7926	79.26%
CYP2D6 inhibition	-	0.7926	79.26%
CYP1A2 inhibition	+	0.8188	81.88%
CYP2C8 inhibition	-	0.7066	70.66%
CYP inhibitory promiscuity	-	0.5488	54.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6191	61.91%
Eye corrosion	-	0.9927	99.27%
Eye irritation	+	0.9447	94.47%
Skin irritation	-	0.5260	52.60%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7835	78.35%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.7813	78.13%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5524	55.24%
Acute Oral Toxicity (c)	II	0.4796	47.96%
Estrogen receptor binding	+	0.7142	71.42%
Androgen receptor binding	+	0.7809	78.09%
Thyroid receptor binding	+	0.5974	59.74%
Glucocorticoid receptor binding	+	0.8140	81.40%
Aromatase binding	+	0.6904	69.04%
PPAR gamma	+	0.7810	78.10%
Honey bee toxicity	-	0.8997	89.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8418	84.18%

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	99.09%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.57%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	88.86%	85.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.60%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.37%	99.15%
CHEMBL3194	P02766	Transthyretin	84.91%	90.71%
CHEMBL2581	P07339	Cathepsin D	84.21%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.12%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.20%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.85%	90.71%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.63%	85.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.86%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	80.62%	94.73%

Plants that contains it

• Scutellaria barbata

Cross-Links

• PubChem: 42608117
• NPASS: NPC145353