(2S)-2-amino-4-{[(23R)-4-[(4S)-4-amino-4-carboxybutanamido]-5,8,19,22-tetraoxo-1,2-dithia-6,9,13,18,21-pentaazacyclotetracosan-23-yl]carbamoyl}butanoic acid; trifluoroacetic acid

• ChemBase ID: 154617
• Molecular Formular: C29H48F3N9O12S2
• Molecular Mass: 835.8697296
• Monoisotopic Mass: 835.28159468
• SMILES: C1CCNC(=O)CNC(=O)[C@@H](CSSCC(C(=O)NCC(=O)NCCCNC1)NC(=O)CC[C@@H](C(=O)O)N)NC(=O)CC[C@@H](C(=O)O)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C1NCCCNCCCCNC(=O)CNC(=O)[C@@H](CSSCC(C(=O)NC1)NC(=O)CC[C@@H](C(=O)O)N)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C27H47N9O10S2.C2HF3O2/c28-16(26(43)44)4-6-20(37)35-18-14-47-48-15-19(36-21(38)7-5-17(29)27(45)46)25(42)34-13-23(40)32-11-3-9-30-8-1-2-10-31-22(39)12-33-24(18)41;3-2(4,5)1(6)7/h16-19,30H,1-15,28-29H2,(H,31,39)(H,32,40)(H,33,41)(H,34,42)(H,35,37)(H,36,38)(H,43,44)(H,45,46);(H,6,7)/t16-,17-,18-,19?;/m0./s1
• InChIKey: BLTBWJNAZIKNTL-QZBRSAASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(23R)-4-[(4S)-4-amino-4-carboxybutanamido]-5,8,19,22-tetraoxo-1,2-dithia-6,9,13,18,21-pentaazacyclotetracosan-23-yl]carbamoyl}butanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(23R)-4-[(4S)-4-amino-4-carboxybutanamido]-5,8,19,22-tetraoxo-1,2-dithia-6,9,13,18,21-pentaazacyclotetracosan-23-yl]carbamoyl}butanoic acid; trifluoroacetic acid
• Synonyms: N1,N8-Bis(glutathionyl)spermidine disulfide; Trypanothione trifluoroacetate salt

Database IDs

• MDL Number: MFCD17215942
• Beilstein Number: 3645155
• PubChem SID: 162248755
• PubChem CID: 71311912

CALCULATED PROPERTIES

• Acid pKa: 1.4448569
• H Acceptors: 13
• H Donor: 11
• LogD (pH = 5.5): -14.058653
• LogD (pH = 7.4): -12.724388
• Log P: -11.493564
• Molar Refractivity: 175.223 cm^3
• Polarizability: 69.10474 Å^3
• Polar Surface Area: 313.27 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H47N9O10S2 · xC2HF3O2

DETAILS

Sigma Aldrich - 04555

Biochem/physiol Actions
Metabolite in the glutathione metabolism. A novel bis(glutathionyl)spermidine cofactor for glutathione reductase in trypanosomatids1.