(2S,4R)-4-({2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[(2S,3S)-3-methyl-N-{[(3-methylbutanoyl)oxy]methyl}-2-{[(2R)-1-methylpiperidin-2-yl]formamido}pentanamido]pentyl]-1,3-thiazol-4-yl}formamido)-5-(4-hydroxyphenyl)-2-methylpentanoic acid

• ChemBase ID: 153927
• Molecular Formular: C43H65N5O10S
• Molecular Mass: 844.0687
• Monoisotopic Mass: 843.44521431
• SMILES: CC[C@H](C)[C@@H](C(=O)N(COC(=O)CC(C)C)[C@H](C[C@H](c1nc(cs1)C(=O)N[C@@H](Cc1ccc(cc1)O)C[C@H](C)C(=O)O)OC(=O)C)C(C)C)NC(=O)[C@H]1CCCCN1C
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N([C@@H](C(C)C)C[C@H](c1scc(n1)C(=O)N[C@H](C[C@@H](C(=O)O)C)Cc1ccc(cc1)O)OC(=O)C)COC(=O)CC(C)C)NC(=O)[C@H]1CCCCN1C)C
• InChI: InChI=1S/C43H65N5O10S/c1-10-27(6)38(46-40(53)34-13-11-12-18-47(34)9)42(54)48(24-57-37(51)19-25(2)3)35(26(4)5)22-36(58-29(8)49)41-45-33(23-59-41)39(52)44-31(20-28(7)43(55)56)21-30-14-16-32(50)17-15-30/h14-17,23,25-28,31,34-36,38,50H,10-13,18-22,24H2,1-9H3,(H,44,52)(H,46,53)(H,55,56)/t27-,28-,31+,34+,35+,36+,38-/m0/s1
• InChIKey: IBEDDHUHZBDXGB-OEJISELMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-4-({2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[(2S,3S)-3-methyl-N-{[(3-methylbutanoyl)oxy]methyl}-2-{[(2R)-1-methylpiperidin-2-yl]formamido}pentanamido]pentyl]-1,3-thiazol-4-yl}formamido)-5-(4-hydroxyphenyl)-2-methylpentanoic acid
• IUPAC Traditional name: (2S,4R)-4-({2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[(2S,3S)-3-methyl-N-{[(3-methylbutanoyl)oxy]methyl}-2-{[(2R)-1-methylpiperidin-2-yl]formamido}pentanamido]pentyl]-1,3-thiazol-4-yl}formamido)-5-(4-hydroxyphenyl)-2-methylpentanoic acid
• Synonyms: TubA; Tubulysin A

Database IDs

• CAS Number: 205304-86-5
• MDL Number: MFCD12912448
• PubChem SID: 162248066
• PubChem CID: 12134544

CALCULATED PROPERTIES

• Acid pKa: 3.6915255
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.3583734
• LogD (pH = 7.4): 2.9877465
• Log P: 3.3528643
• Molar Refractivity: 221.8516 cm^3
• Polarizability: 87.29421 Å^3
• Polar Surface Area: 204.77 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: organic solvents: soluble
• Apperance: colorless or white film

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Biological Source: from Streptomyces sp.
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C43H65N5O10S

DETAILS

Sigma Aldrich - T3327

Biochem/physiol Actions
Tubulysin A is a novel antibiotic, which is anti-microtubule, anti-mitotic, apoptosis inducer, anticancer, anti-angiogenic, and antiproliferative. Tubulysins are cytotoxic peptides, which include 9 members (A-I). Tubulysin A has potential application as an anticancer agent. It arrests cells in the G2/M phase. Tubulysin A inhibits polymerization more efficiently than vinblastine and induces depolymerization of isolated microtubules. Tubulysin A has potent cytostatic effects on various tumor cell lines with IC50 in the picomolar range.