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

• ChemBase ID: 130063
• Molecular Formular: C30H46N4O16
• Molecular Mass: 718.70344
• Monoisotopic Mass: 718.29088141
• SMILES: CC(C)C/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)CC([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](CC([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\CC(C)C)O)O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C30H46N4O16/c1-11(2)5-4-6-16(38)32-19-23(43)20(40)14(47-29(19)50-28-18(31-12(3)36)22(42)21(41)15(10-35)48-28)9-13(37)26-24(44)25(45)27(49-26)34-8-7-17(39)33-30(34)46/h4,6-8,11,13-15,18-29,35,37,40-45H,5,9-10H2,1-3H3,(H,31,36)(H,32,38)(H,33,39,46)/t13?,14-,15-,18-,19-,20+,21-,22-,23-,24+,25-,26-,27-,28-,29+/m1/s1
• InChIKey: ZHSGGJXRNHWHRS-JKHWFIQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5R,6R)-6-{2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl}-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-3-yl]-5-methylhex-2-enamide
• IUPAC Traditional name: N-[(2S,3R,4R,5R,6R)-6-{2-[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl}-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-3-yl]-5-methylhex-2-enamide
• Synonyms: NSC 177382; Tunicamycin

Database IDs

• CAS Number: 11089-65-9
• PubChem SID: 162224348
• PubChem CID: 71308289; 6433557
• CHEMBL: 505513
• MeSH Name: Tunicamycin
• Wikipedia Title: Tunicamycin

CALCULATED PROPERTIES

• Rotatable Bonds: 12
• Lipinski's Rule of Five: false
• Acid pKa: 9.6987
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -4.737442
• LogD (pH = 7.4): -4.7394524
• Log P: -4.737299
• Molar Refractivity: 163.451 cm^3
• Polarizability: 65.74846 Å^3
• Polar Surface Area: 306.37 Å^2

PROPERTIES

Safety Information

• Risk Statements: 28
• Safety Statements: 28-37/39-45