N-[(2S,3R,4R,5R,6R)-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-2-{[(2S,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-3-yl]-12-methyltridec-2-enamide

• ChemBase ID: 158488
• Molecular Formular: C37H60N4O16
• Molecular Mass: 816.8895
• Monoisotopic Mass: 816.40043186
• SMILES: CC(C)CCCCCCCC/C=C\C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC(=O)C)C[C@H]([C@@H]1[C@H]([C@H]([C@@H](O1)n1ccc(=O)[nH]c1=O)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@@H]2O[C@H](C[C@H]([C@H]3O[C@H]([C@@H]([C@@H]3O)O)n3ccc(=O)[nH]c3=O)O)[C@@H]([C@@H]([C@H]2NC(=O)/C=C\CCCCCCCCC(C)C)O)O)[C@H]([C@@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C37H60N4O16/c1-18(2)12-10-8-6-4-5-7-9-11-13-23(45)39-26-30(50)27(47)21(54-36(26)57-35-25(38-19(3)43)29(49)28(48)22(17-42)55-35)16-20(44)33-31(51)32(52)34(56-33)41-15-14-24(46)40-37(41)53/h11,13-15,18,20-22,25-36,42,44,47-52H,4-10,12,16-17H2,1-3H3,(H,38,43)(H,39,45)(H,40,46,53)/t20-,21-,22+,25+,26-,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+/m1/s1
• InChIKey: YJQCOFNZVFGCAF-LFOPQCCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5R,6R)-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-2-{[(2S,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-3-yl]-12-methyltridec-2-enamide
• IUPAC Traditional name: N-[(2S,3R,4R,5R,6R)-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-2-{[(2S,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-3-yl]-12-methyltridec-2-enamide
• Synonyms: Tunicamycin from Streptomyces sp.; Tunicamycin from Streptomyces sp. 来源于链霉菌 属

Database IDs

• CAS Number: 11089-65-9
• MDL Number: MFCD00065709
• Beilstein Number: 6888090
• PubChem SID: 162252624
• PubChem CID: 71312646

CALCULATED PROPERTIES

• Acid pKa: 9.698712
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -1.6254615
• LogD (pH = 7.4): -1.6274718
• Log P: -1.6253184
• Molar Refractivity: 195.658 cm^3
• Polarizability: 78.46738 Å^3
• Polar Surface Area: 306.37 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: YO7980200
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 28-37/39-45
• 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 2
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - 93755

General description
mixture of homologous tunicamycins, which differ in the aliphatic side chain
Other Notes
Glucosamine containing antibiotic with cell-surface altering properties, enhances the antiviral and antigrowth effects of interferon1; Many important biochemical functions are inhibited by tunicamycin, such as glycoprotein biosynthesis in yeast2; The synthesis of polyisoprenol sugars in bacteria3