(4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrate

• ChemBase ID: 154889
• Molecular Formular: C29H41N5O9
• Molecular Mass: 603.66394
• Monoisotopic Mass: 603.29042792
• SMILES: CC(C)(C)NCC(=O)Nc1cc(c2c(c1O)C(=O)C1=C([C@]3([C@@H](C[C@@H]1C2)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)N(C)C.O
• Canonical SMILES: O=C(Nc1cc(N(C)C)c2c(c1O)C(=O)C1=C(O)[C@]3([C@@H](C[C@@H]1C2)[C@H](N(C)C)C(=C(C3=O)C(=O)N)O)O)CNC(C)(C)C.O
• InChI: InChI=1S/C29H39N5O8.H2O/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36;/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35);1H2/t12-,14-,21-,29-;/m0./s1
• InChIKey: PMPLAEFBZIFHAR-KXLOKULZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrate
• IUPAC Traditional name: tigecycline hydrate
• Synonyms: 9-t-Butylglycylamido-minocycline hydrate; TBG-MINO; Tigecyclin; Tygacil; Tigecycline hydrate

Database IDs

• CAS Number: 1229002-07-6
• PubChem SID: 162249027
• PubChem CID: 71312020

CALCULATED PROPERTIES

• Acid pKa: 0.25205672
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -5.231753
• LogD (pH = 7.4): -5.187741
• Log P: -5.147121
• Molar Refractivity: 159.3431 cm^3
• Polarizability: 59.23616 Å^3
• Polar Surface Area: 205.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥3 mg/mL (warmed)
• Apperance: off-white to yellow-brown powder
• Optical Rotation: [α]/D -160 to 170°, c = 0.15 in methanol

Safety Information

• RTECS: QI7619500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 61-36-52-64
• Safety Statements: 13-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H319-H360
• GHS Precautionary statements: P201-P305 + P351 + P338-P308 + P313
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C29H39N5O8 · xH2O

DETAILS

Sigma Aldrich - PZ0021

Other Notes
air sensitive
Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Tigecycline is a broad spectrum glycylcycline antibiotic. Tigecycline is bacteriostatic, that inhibits protein synthesis by binding to the 30S ribosomal subunit of bacteria and thereby blocking entry of Aminoacyl-tRNA into the A site of the ribosome during prokaryotic translation. Tigecycline is active against resistant strains of gram-positive and gram-negative bacteria, avoiding the two most common mechanisms of resistance to the tetracycline antimicrobials: tetracycline efflux pump proteins and ribosomal protection proteins.