5-{[(2,5-dihydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid

• ChemBase ID: 131306
• Molecular Formular: C14H13NO5
• Molecular Mass: 275.25672
• Monoisotopic Mass: 275.07937252
• SMILES: c1cc(c(cc1NCc1cc(ccc1O)O)C(=O)O)O
• Canonical SMILES: Oc1ccc(c(c1)CNc1ccc(c(c1)C(=O)O)O)O
• InChI: InChI=1S/C14H13NO5/c16-10-2-4-12(17)8(5-10)7-15-9-1-3-13(18)11(6-9)14(19)20/h1-6,15-18H,7H2,(H,19,20)
• InChIKey: LULATDWLDJOKCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(2,5-dihydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid
• IUPAC Traditional name: 5-{[(2,5-dihydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid
• Synonyms: 5-(2,5-Dihydroxybenzylamino)-2-hydroxybenzoic acid; 5-(2,5-Dihydroxybenzylamino)salicylic acid; N-(2,5-Dihydroxybenzyl)-5-aminosalicylic acid; Lavendustin C; NSC 666251; 5-(2,5-Dihydroxybenzylamino)-2-hydroxybenzoic Acid; N-(2′,5′-Dihydroxybenzyl)-5-aminosalicylic acid; Compound 5; HDBA; [2-Hydroxy-5-[N-(2′,5′-dihydroxybenzyl)amino]benzoic acid; Lavendustin C; 5-(2,5-二羟基苄基氨基)水杨酸; N-(2,5-二羟基苄基)-5-氨基水杨酸; 5-(2,5-二羟基苄基氨基)-2-羟基苯甲酸

Database IDs

• CAS Number: 125697-93-0
• MDL Number: MFCD00153955
• Beilstein Number: 6657779
• PubChem SID: 24896277; 24863425; 162225584
• PubChem CID: 3896

CALCULATED PROPERTIES

• Acid pKa: 2.5421987
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.70443654
• LogD (pH = 7.4): -0.56249267
• Log P: 0.87845665
• Molar Refractivity: 74.0633 cm^3
• Polarizability: 27.096725 Å^3
• Polar Surface Area: 110.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble; ethanol: soluble; Methanol
• Apperance: Brown Solid; solid
• Melting Point: >185°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... EGFR(1956), ERBB2(2064), LCK(3932)

Product Information

• Purity: ≥97%; ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C14H13NO5

DETAILS

Sigma Aldrich - L1289

Biochem/physiol Actions
Potent inhibitor of protein tyrosine kinases.

Sigma Aldrich - 37618

Other Notes
Potent tyrosine kinase inhibitor1

Toronto Research Chemicals - D452000

Shows potent tyrosine kinase inhibitory activity.

REFERENCES

• Onoda, T., et al.: Journal of Natural Products, 52, 6, 1252 (1989)
• Trapp, J., et al.: J. Med. Chem., 49, 7307 (1989)
• Varela, M., et al.: Virol., 371, 206 (1989)