sodium (4E)-9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}non-4-enoate

• ChemBase ID: 177096
• Molecular Formular: C26H41NaO9
• Molecular Mass: 520.58811
• Monoisotopic Mass: 520.26482717
• SMILES: [C@H]([C@@H]([C@H]1[C@H](C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCC/C=C/CCC(=O)[O-])/C)O1)C)(O)C.[Na+]
• Canonical SMILES: [O-]C(=O)CC/C=C/CCCCOC(=O)/C=C(/C[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)C[C@@H]1O[C@H]1[C@H]([C@@H](O)C)C)\C.[Na+]
• InChI: InChI=1S/C26H42O9.Na/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27;/h4,6,13,17-21,24-27,31-32H,5,7-12,14-15H2,1-3H3,(H,28,29);/q;+1/p-1/b6-4+,16-13+;/t17-,18-,19-,20-,21-,24+,25-,26-;/m0./s1
• InChIKey: SMEUVQBMXYPYPL-JPZIBMRNSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4E)-9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}non-4-enoate
• IUPAC Traditional name: sodium (4E)-9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}non-4-enoate
• Synonyms: [1(E),2E,8[2S,3S(1S,2S)]]-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-L-talo-Non-2-enonic Acid 8-Carboxy-5-octenyl Ester Monosodium Salt; Sodium Pseudomonate D; Pseudomonic Acid D Sodium

Database IDs

• CAS Number: 85178-60-5
• PubChem SID: 164233006
• PubChem CID: 71751871

CALCULATED PROPERTIES

• Acid pKa: 4.762416
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.2795414
• LogD (pH = 7.4): -0.4967681
• Log P: 2.089404
• Molar Refractivity: 141.3478 cm^3
• Polarizability: 51.1742 Å^3
• Polar Surface Area: 148.88 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P839520

An antibiotic isolated from Pseudomonas fluorescens.

REFERENCES

• Banks, R.M., et al.: J. Antibiot., 41, 609 (1988)