4-hydroxy-3-[2-hydroxy-5-[(2S,3S)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl]benzoic acid

Details

• Internal ID: 9f96840b-ea11-4d16-9aa9-20d1f4435d18
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: 4-hydroxy-3-[2-hydroxy-5-[(2S,3S)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl]benzoic acid
• InChI: InChI=1S/C22H16O9/c23-11-7-16(26)18-17(8-11)31-21(20(28)19(18)27)9-1-3-14(24)12(5-9)13-6-10(22(29)30)2-4-15(13)25/h1-8,20-21,23-26,28H,(H,29,30)/t20-,21+/m1/s1
• InChI Key: HPQHGBFQHWMBIV-RTWAWAEBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₆O₉
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.07943208 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8640	86.40%
Caco-2	-	0.9321	93.21%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6253	62.53%
OATP2B1 inhibitior	-	0.5493	54.93%
OATP1B1 inhibitior	+	0.9242	92.42%
OATP1B3 inhibitior	-	0.4190	41.90%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5899	58.99%
P-glycoprotein inhibitior	-	0.5556	55.56%
P-glycoprotein substrate	-	0.9015	90.15%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6242	62.42%
CYP2D6 substrate	-	0.8502	85.02%
CYP3A4 inhibition	-	0.7576	75.76%
CYP2C9 inhibition	+	0.7183	71.83%
CYP2C19 inhibition	-	0.8598	85.98%
CYP2D6 inhibition	-	0.9636	96.36%
CYP1A2 inhibition	-	0.8162	81.62%
CYP2C8 inhibition	+	0.6967	69.67%
CYP inhibitory promiscuity	-	0.7432	74.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7193	71.93%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.4913	49.13%
Skin irritation	+	0.5380	53.80%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5589	55.89%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8746	87.46%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7111	71.11%
Acute Oral Toxicity (c)	II	0.6536	65.36%
Estrogen receptor binding	+	0.7274	72.74%
Androgen receptor binding	+	0.7226	72.26%
Thyroid receptor binding	+	0.5455	54.55%
Glucocorticoid receptor binding	+	0.7005	70.05%
Aromatase binding	-	0.6904	69.04%
PPAR gamma	+	0.6461	64.61%
Honey bee toxicity	-	0.8918	89.18%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9567	95.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	96.98%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	96.12%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.18%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.28%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.13%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.01%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.58%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.73%	93.40%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.45%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.20%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.54%	81.11%
CHEMBL2535	P11166	Glucose transporter	82.14%	98.75%
CHEMBL1811	P34995	Prostanoid EP1 receptor	81.99%	95.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.79%	94.42%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.28%	97.09%

Plants that contains it

• Hypnum cupressiforme

Cross-Links

• PubChem: 162983898
• LOTUS: LTS0160563
• wikiData: Q105031819