5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid

• ChemBase ID: 132968
• Molecular Formular: C25H22N4O8
• Molecular Mass: 506.46418
• Monoisotopic Mass: 506.14376368
• SMILES: Cc1c(c(c(nc1C(=O)O)c1ccc2c(n1)C(=O)C(=C(C2=O)OC)N)N)c1ccc(c(c1O)OC)OC
• Canonical SMILES: COC1=C(N)C(=O)c2c(C1=O)ccc(n2)c1nc(C(=O)O)c(c(c1N)c1ccc(c(c1O)OC)OC)C
• InChI: InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)
• InChIKey: PVYJZLYGTZKPJE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
• IUPAC Traditional name: nigrin
• Synonyms: Bruneomycin; Nigrin; Streptonigrin from Streptomyces flocculus

Database IDs

• CAS Number: 3930-19-6
• EC Number: 223-501-8
• MDL Number: MFCD00063401
• Beilstein Number: 599390
• PubChem SID: 24899458; 162227245
• PubChem CID: 5351165

CALCULATED PROPERTIES

• Acid pKa: 3.8939507
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -0.73105085
• LogD (pH = 7.4): -2.248122
• Log P: 1.0583267
• Molar Refractivity: 132.9024 cm^3
• Polarizability: 51.534283 Å^3
• Polar Surface Area: 197.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: TJ7350000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 28
• Safety Statements: 53-28-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C25H22N4O8

DETAILS

Sigma Aldrich - S1014

Biochem/physiol Actions
Streptonigrin (SN) is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by SN are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated.