(2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl (2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanamido]-N,3-dimethylbutanamido]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate

• ChemBase ID: 153752
• Molecular Formular: C45H68N6O9
• Molecular Mass: 837.05622
• Monoisotopic Mass: 836.50477779
• SMILES: CC(C)[C@@H](C(=O)N(C)[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)O[C@@H](C(C)C)C(=O)N1[C@H](C(=CC1=O)OC)Cc1ccccc1)NC(=O)[C@H](C(C)C)N(C)C
• Canonical SMILES: COC1=CC(=O)N([C@H]1Cc1ccccc1)C(=O)[C@H](C(C)C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](N(C(=O)[C@H](C(C)C)NC(=O)[C@@H](N(C)C)C(C)C)C)C(C)C
• InChI: InChI=1S/C45H68N6O9/c1-26(2)36(46-40(53)37(27(3)4)47(9)10)42(55)48(11)38(28(5)6)43(56)49-22-16-20-31(49)41(54)50-23-17-21-32(50)45(58)60-39(29(7)8)44(57)51-33(34(59-12)25-35(51)52)24-30-18-14-13-15-19-30/h13-15,18-19,25-29,31-33,36-39H,16-17,20-24H2,1-12H3,(H,46,53)/t31-,32-,33-,36-,37-,38-,39-/m0/s1
• InChIKey: LQKSHSFQQRCAFW-CCVNJFHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl (2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanamido]-N,3-dimethylbutanamido]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
• IUPAC Traditional name: (2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl (2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanamido]-N,3-dimethylbutanamido]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
• Synonyms: (5S)-1-[(2S)-O-(N,N-Val-Val-N-Me-Val-Pro-Pro)-2-hydroxyisovaleryl]-2-oxo-4-methoxy-5-benzyl-3-pyrroline; Dolastatin 15

Database IDs

• CAS Number: 123884-00-4
• MDL Number: MFCD00236968
• PubChem SID: 162247891; 24893943
• PubChem CID: 9918978

CALCULATED PROPERTIES

• Acid pKa: 9.828692
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 1.4148394
• LogD (pH = 7.4): 3.1796803
• Log P: 3.7981162
• Molar Refractivity: 227.1618 cm^3
• Polarizability: 88.88065 Å^3
• Polar Surface Area: 166.18 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C45H68N6O9

DETAILS

Sigma Aldrich - D5566

Amino Acid Sequence
Val-Val-NMe-Val-Pro-Pro-2-hydroxyisovaleryl-2-oxo-4-methoxy-5-benzyl-3-pyrroline
Application
An anti-neoplastic pseudopeptide originally isolated from the sea hare Dolabella auricularia. Reported to interact with tubulin and induce apoptosis. Potent inhibitor of the proliferation of murine and cancer cell lines as well as of hematopoietic progenitor cells.