(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-(2H3)methyl(4,4-2H2)but-2-enoic acid

• ChemBase ID: 174702
• Molecular Formular: C17H28O7
• Molecular Mass: 344.40002
• Monoisotopic Mass: 344.18350324
• SMILES: [C@H]1(C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)O)/C)[C@H]([C@H]([C@@H](O)C)C)O1
• Canonical SMILES: C/C(=C\C(=O)O)/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
• InChI: InChI=1S/C17H28O7/c1-8(5-14(19)20)4-12-16(22)15(21)11(7-23-12)6-13-17(24-13)9(2)10(3)18/h5,9-13,15-18,21-22H,4,6-7H2,1-3H3,(H,19,20)/b8-5+/t9-,10-,11-,12-,13-,15+,16-,17-/m0/s1
• InChIKey: IUBMRJVNZLQSHU-FDJBSCRHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-(^2H₃)methyl(4,4-^2H₂)but-2-enoic acid
• IUPAC Traditional name: (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-(^2H₃)methyl(4,4-^2H₂)but-2-enoic acid
• Synonyms: Monic Acid-d5; Monic Acid A-d5; (2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-L-talo-non-2-enonic Acid-d5; [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-d5

Database IDs

• PubChem SID: 164230612
• PubChem CID: 71750777

CALCULATED PROPERTIES

• Acid pKa: 4.4280405
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.2601719
• LogD (pH = 7.4): -3.0206323
• Log P: -0.15440229
• Molar Refractivity: 86.081 cm^3
• Polarizability: 34.216183 Å^3
• Polar Surface Area: 119.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M520502

Labelled Monic Acid A, the major metabolite of the antibiotic Mupirocin (M794000). Monic Acid A is also used in the preparation of cereal herbicide and mycoplasma inhibitors.

REFERENCES

• Kudoh, S. et al.: Kuromatogurafi, 13, 269 (1992)
• Bryan, I.B. et al.: Brighton Crop Prot. Conf. Weeds, 2, 725 (1992)
• Banks, R. et al.: J. Antibiot., 41, 609 (1992)