2-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]acetic acid

Details

• Internal ID: 0d0a2b94-fcfa-4521-b02d-c3fac9622cc1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: 2-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]acetic acid
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(C3=C(C=C(C=C3O2)O)O)CC(=O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2C(C(C3=C(C=C(C=C3O2)O)O)CC(=O)O)O)O)O
• InChI: InChI=1S/C17H16O8/c18-8-4-12(21)15-9(6-14(22)23)16(24)17(25-13(15)5-8)7-1-2-10(19)11(20)3-7/h1-5,9,16-21,24H,6H2,(H,22,23)
• InChI Key: SBSHGFDVQPIUCS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₈
• Molecular Weight: 348.30 g/mol
• Exact Mass: 348.08451746 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 1.56
• H-Bond Acceptor: 7
• 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	+	0.6930	69.30%
Caco-2	-	0.9495	94.95%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5082	50.82%
OATP2B1 inhibitior	-	0.5691	56.91%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.8226	82.26%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8714	87.14%
P-glycoprotein inhibitior	-	0.9204	92.04%
P-glycoprotein substrate	-	0.9325	93.25%
CYP3A4 substrate	-	0.5223	52.23%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.7103	71.03%
CYP3A4 inhibition	-	0.8024	80.24%
CYP2C9 inhibition	-	0.9373	93.73%
CYP2C19 inhibition	-	0.9620	96.20%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.9499	94.99%
CYP2C8 inhibition	+	0.5099	50.99%
CYP inhibitory promiscuity	-	0.9092	90.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6427	64.27%
Eye corrosion	-	0.9940	99.40%
Eye irritation	+	0.8232	82.32%
Skin irritation	-	0.6395	63.95%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4674	46.74%
Micronuclear	+	0.8218	82.18%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8293	82.93%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8072	80.72%
Acute Oral Toxicity (c)	IV	0.3470	34.70%
Estrogen receptor binding	-	0.5708	57.08%
Androgen receptor binding	+	0.6990	69.90%
Thyroid receptor binding	-	0.4872	48.72%
Glucocorticoid receptor binding	+	0.7180	71.80%
Aromatase binding	-	0.5459	54.59%
PPAR gamma	+	0.6070	60.70%
Honey bee toxicity	-	0.9034	90.34%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8778	87.78%

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	98.41%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.22%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.10%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.80%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.72%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.26%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.65%	99.17%
CHEMBL3194	P02766	Transthyretin	88.19%	90.71%
CHEMBL2581	P07339	Cathepsin D	87.31%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.35%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.31%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.89%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.65%	99.23%

Plants that contains it

• Davallia divaricata
• Dryopteris crassirhizoma

Cross-Links

• PubChem: 14463077
• LOTUS: LTS0243558
• wikiData: Q105249668