5-hydroxy-6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid

• ChemBase ID: 2362
• Molecular Formular: C17H11NO8
• Molecular Mass: 357.27114
• Monoisotopic Mass: 357.04846632
• SMILES: c1(cc2c(c3c1c(cc1c3ccc(c1OC)O)[N+](=O)[O-])OCO2)C(=O)O
• Canonical SMILES: COc1c(O)ccc2c1cc([N+](=O)[O-])c1c2c2OCOc2cc1C(=O)O
• InChI: InChI=1S/C17H11NO8/c1-24-15-8-4-10(18(22)23)13-9(17(20)21)5-12-16(26-6-25-12)14(13)7(8)2-3-11(15)19/h2-5,19H,6H2,1H3,(H,20,21)
• InChIKey: UCLGCTLOEZZSLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid
• IUPAC Traditional name: 5-hydroxy-6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid
• Synonyms: 9-Hydroxy-8-Methoxy-6-Nitro-Phenanthrol[3,4-D][1,3]Dioxole-5-Carboxylic Acid

Database IDs

• PubChem SID: 46505836; 160965813
• PubChem CID: 1941

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3241537
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.55182886
• LogD (pH = 7.4): -0.71110284
• Log P: 2.7117634
• Molar Refractivity: 87.7503 cm^3
• Polarizability: 35.17982 Å^3
• Polar Surface Area: 131.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.53
• LOG S: -3.68
• Solubility (Water): 7.47e-02 g/l

DETAILS

DrugBank - DB02636

Drug information: experimental