sodium 6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2(7),3,5,8,11,13(17)-heptaene-11-carboxylate

• ChemBase ID: 133843
• Molecular Formular: C17H10NNaO7
• Molecular Mass: 363.25357
• Monoisotopic Mass: 363.03549595
• SMILES: COc1cccc2c1cc(c1c2c2c(cc1C(=O)[O-])OCO2)[N+](=O)[O-].[Na+]
• Canonical SMILES: COc1cccc2c1cc([N+](=O)[O-])c1c2c2OCOc2cc1C(=O)[O-].[Na+]
• InChI: InChI=1S/C17H11NO7.Na/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13;/h2-6H,7H2,1H3,(H,19,20);/q;+1/p-1
• InChIKey: BQVOPWJSBBMGBR-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^2,^7.0^1^3,^1^7]heptadeca-1(10),2(7),3,5,8,11,13(17)-heptaene-11-carboxylate
• IUPAC Traditional name: sodium 6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^2,^7.0^1^3,^1^7]heptadeca-1(10),2(7),3,5,8,11,13(17)-heptaene-11-carboxylate
• Synonyms: Aristolochic acid sodium salt; Aristolochic acid I sodium salt

Database IDs

• CAS Number: 10190-99-5
• EC Number: 233-463-4
• MDL Number: MFCD00210760
• PubChem SID: 162228120; 24891454
• PubChem CID: 154914

CALCULATED PROPERTIES

• Acid pKa: 3.3240964
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.85536474
• LogD (pH = 7.4): -0.40555608
• Log P: 3.0153286
• Molar Refractivity: 96.6065 cm^3
• Polarizability: 34.450043 Å^3
• Polar Surface Area: 113.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: orange-brown powder

Safety Information

• RTECS: SF8281000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-40
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H351
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• 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 1544 6.1/PG 3

Product Information

• Purity: ≥97%

DETAILS

Sigma Aldrich - A9451

Biochem/physiol Actions
Component of some Chinese herbal medicines, and responsible for their nephrotoxicity. Prodrug activated by reduction of the nitro group to an amine, which forms cytotoxic DNA adducts.1