(2R)-2-[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido]-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

• ChemBase ID: 155386
• Molecular Formular: C20H25N5O10
• Molecular Mass: 495.44
• Monoisotopic Mass: 495.16014203
• SMILES: C[C@H]([C@@H](c1ccc(cn1)O)O)[C@@H](C(=O)N[C@H]([C@@H]1[C@H]([C@H]([C@@H](O1)n1ccc(=O)[nH]c1=O)O)O)C(=O)O)N
• Canonical SMILES: OC(=O)[C@@H]([C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=O)[nH]c1=O)NC(=O)[C@H]([C@@H]([C@@H](c1ccc(cn1)O)O)C)N
• InChI: InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12+,13-,14-,15+,16+,18+/m0/s1
• InChIKey: WWJFFVUVFNBJTN-JKEIIPFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido]-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
• IUPAC Traditional name: (R)-[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido][(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
• Synonyms: Nikkomycin; Nikkomycin Z from Streptomyces tendae

Database IDs

• CAS Number: 59456-70-1
• MDL Number: MFCD00869648
• Beilstein Number: 873216
• PubChem SID: 162249524; 24897849; 24886404
• PubChem CID: 9935526

CALCULATED PROPERTIES

• Acid pKa: 2.6059542
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -5.647641
• LogD (pH = 7.4): -5.7942843
• Log P: -5.64964
• Molar Refractivity: 111.8356 cm^3
• Polarizability: 44.594955 Å^3
• Polar Surface Area: 244.87 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: BA2928200
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥90% (HPLC); ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C20H25N5O10

DETAILS

Sigma Aldrich - N8028

Application
Nikkomycin Z is used as a selective competitive inhibitor of chitin synthetase 3 in studies on fungal cell wall development. It is a potential treatment for human Encephalitozoon hellem, a microsporidian species1 and is used to study the changes of chitin and β--glucan under Nikkomycin Z exposure2.
Biochem/physiol Actions
Nikkomycin Z inhibits chitin synthase from converting UDP-GlcNAc into cell wall chitin due to its structural resemblance to UDP-N-acetylglucosamine3. Nikkomycin Z has potent antifungal, insecticidal and acaridicial activity.