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

• ChemBase ID: 105103
• Molecular Formular: C21H19NO6
• Molecular Mass: 381.37866
• Monoisotopic Mass: 381.12123733
• SMILES: OC(=O)c1cc(ccc1O)N(Cc1ccccc1O)Cc1cc(O)ccc1O
• Canonical SMILES: Oc1ccc(c(c1)CN(c1ccc(c(c1)C(=O)O)O)Cc1ccccc1O)O
• InChI: InChI=1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28)
• InChIKey: ULTTYPMRMMDONC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid
• IUPAC Traditional name: 5-{[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid
• Synonyms: 5-[[(2,5-Dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy-benzoic Acid; NSC 678027; LAVENDUSTIN A; 5-[[(2,5-Dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid; Lavendustin A

Database IDs

• CAS Number: 125697-92-9
• MDL Number: MFCD00153822
• PubChem SID: 24896314; 162091859
• PubChem CID: 3894

CALCULATED PROPERTIES

• Acid pKa: 3.4733346
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 2.5796022
• LogD (pH = 7.4): 1.2225813
• Log P: 4.452512
• Molar Refractivity: 104.8916 cm^3
• Polarizability: 39.10215 Å^3
• Polar Surface Area: 121.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; Methanol; methanol: soluble
• Apperance: crystalline; Off-White to Pale Yellow Solid
• Melting Point: 206-208°C

Safety Information

• Storage Condition: 0°C, Desiccate, Protect from light; -20°C Freezer
• Storage Warning: Moisture Sensitive: Hygroscopic
• German water hazard class: 3
• Personal Protective Equipment: 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: ~85% (TLC)

DETAILS

MP Biomedicals - 02158815

Lavendustin A is a potent and selective inhibitor of the EGF receptor tyrosine kinase (IC₅₀ =11 nM)^1 . It binds to a site on the kinase which is distinct from the ATP and peptide substrate binding sites^2 .

Sigma Aldrich - L2400

Biochem/physiol Actions
Cell-permeable tyrosine kinase inhibitor with little effect on protein kinase A or C. Inhibits NMDA-stimulated cGMP production. Inhibits VEGF-induced angiogenesis.
Physical form
Photosensitive

Toronto Research Chemicals - L215000

A potent tyrosine kinase inhibitor. Inhibition is competitive with ATP and is noncompetitive with the peptide.

REFERENCES

• Onada, T., et al., J. Nat. Prod. , 52 : 1252, (1989).
• Hsu, C.-Y.J., et al., J. Biol. Chem. , 266 : 21105, (1991).
• Onoda, T., et al.: Journal of Natural Products, 52, 6, 1252 (1989)