3-Methoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid

Details

• Internal ID: e514a82b-73cf-4c15-991e-da8b7ddaa7e5
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 3-methoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C(=O)O)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(=O)O)OC2C(C(C(C(O2)CO)O)O)O
• InChI: InChI=1S/C14H18O9/c1-21-8-4-6(13(19)20)2-3-7(8)22-14-12(18)11(17)10(16)9(5-15)23-14/h2-4,9-12,14-18H,5H2,1H3,(H,19,20)
• InChI Key: JYFOSWJYZIVJPO-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₉
• Molecular Weight: 330.29 g/mol
• Exact Mass: 330.09508215 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• CHEBI:167540
• AKOS040738871
• NCGC00385868-01
• PD044523
• 3-methoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• NCGC00385868-01_C14H18O9_4-(Hexopyranosyloxy)-3-methoxybenzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7149	71.49%
Caco-2	-	0.8371	83.71%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6648	66.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9194	91.94%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7784	77.84%
P-glycoprotein inhibitior	-	0.9406	94.06%
P-glycoprotein substrate	-	0.9224	92.24%
CYP3A4 substrate	-	0.5623	56.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8668	86.68%
CYP3A4 inhibition	-	0.8632	86.32%
CYP2C9 inhibition	-	0.8775	87.75%
CYP2C19 inhibition	-	0.9154	91.54%
CYP2D6 inhibition	-	0.9346	93.46%
CYP1A2 inhibition	-	0.8980	89.80%
CYP2C8 inhibition	+	0.5443	54.43%
CYP inhibitory promiscuity	-	0.7229	72.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7412	74.12%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8301	83.01%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7523	75.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.7215	72.15%
Micronuclear	-	0.5067	50.67%
Hepatotoxicity	-	0.7194	71.94%
skin sensitisation	-	0.8743	87.43%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7359	73.59%
Acute Oral Toxicity (c)	III	0.7844	78.44%
Estrogen receptor binding	-	0.7198	71.98%
Androgen receptor binding	-	0.7616	76.16%
Thyroid receptor binding	-	0.5915	59.15%
Glucocorticoid receptor binding	+	0.5527	55.27%
Aromatase binding	-	0.6937	69.37%
PPAR gamma	-	0.5683	56.83%
Honey bee toxicity	-	0.9223	92.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8800	88.00%
Fish aquatic toxicity	-	0.5277	52.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.95%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.82%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.18%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.27%	96.00%
CHEMBL3194	P02766	Transthyretin	88.43%	90.71%
CHEMBL1255126	O15151	Protein Mdm4	87.69%	90.20%
CHEMBL4208	P20618	Proteasome component C5	84.51%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.85%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	81.08%	94.73%
CHEMBL2581	P07339	Cathepsin D	80.63%	98.95%

Plants that contains it

• Aristolochia kaempferi
• Carthamus oxyacantha
• Eurycorymbus cavaleriei
• Hypericum sikokumontanum
• Onobrychis viciifolia
• Picea glauca
• Pinus sylvestris
• Prunus domestica
• Pseudolarix amabilis
• Sargentodoxa cuneata

Cross-Links

• PubChem: 14132336
• LOTUS: LTS0144589
• wikiData: Q105136971