1,6,7-trimethyl-3-(2-methylpropyl)-12-(phenylmethylidene)-1,4,7,10-tetraazacyclododecane-2,5,8,11-tetrone

• ChemBase ID: 155327
• Molecular Formular: C22H30N4O4
• Molecular Mass: 414.498
• Monoisotopic Mass: 414.22670546
• SMILES: CC1C(=O)NC(C(=O)N(/C(=C/c2ccccc2)/C(=O)NCC(=O)N1C)C)CC(C)C
• Canonical SMILES: CC(CC1NC(=O)C(C)N(C)C(=O)CNC(=O)/C(=C\c2ccccc2)/N(C1=O)C)C
• InChI: InChI=1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)
• InChIKey: SIIRBDOFKDACOK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,6,7-trimethyl-3-(2-methylpropyl)-12-(phenylmethylidene)-1,4,7,10-tetraazacyclododecane-2,5,8,11-tetrone
• IUPAC Traditional name: 1,6,7-trimethyl-3-(2-methylpropyl)-12-(phenylmethylidene)-1,4,7,10-tetraazacyclododecane-2,5,8,11-tetrone
• Synonyms: Tentoxin from Alternaria tenuis

Database IDs

• CAS Number: 28540-82-1
• MDL Number: MFCD00133844
• PubChem SID: 162249465; 24900492
• PubChem CID: 5942323

CALCULATED PROPERTIES

• Acid pKa: 11.282122
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5455764
• LogD (pH = 7.4): 0.5455305
• Log P: 0.54558104
• Molar Refractivity: 114.3502 cm^3
• Polarizability: 43.752758 Å^3
• Polar Surface Area: 98.82 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~99% (HPLC)
• Empirical Formula (Hill Notation): C22H30N4O4

DETAILS

Sigma Aldrich - T8019

Application
Tentoxin is a naturally occurring phytotoxic cyclic tetrapeptide that is excreted by the fungi Alternaria alternata and Alternaria tenuis. It induces chlorosis in germinating seedlings of many dicotyledonous plants. Tentoxin has been postulated to inhibit cyclic photophosphorylation by acting as an energy transfer inhibitor at the terminal steps of ATP synthesis and to target the F1 moiety of photosynthetic H+-ATPases. A kinetic analysis of the action of tentoxin on the chloroplast F1 H+-ATPase (CF1) portion of chloroplast ATP synthase has been reported.