(2R,3S)-N-hydroxy-N'-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]butanediamide

• ChemBase ID: 3517
• Molecular Formular: C23H31N3O4S2
• Molecular Mass: 477.63994
• Monoisotopic Mass: 477.17559849
• SMILES: [C@H](C(=O)NO)(CSc1cccs1)[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)Cc1ccccc1
• Canonical SMILES: CNC(=O)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1cccs1)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1
• InChIKey: XFILPEOLDIKJHX-QYZOEREBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-N-hydroxy-N'-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]butanediamide; (2R,3S)-N'-hydroxy-N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]butanediamide
• IUPAC Traditional name: (2R,3S)-N-hydroxy-N'-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]butanediamide; (2R,3S)-N'-hydroxy-N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]succinamide; batimastat
• Synonyms: BB94; Batimastat; Batimastat; Batimastat (BB-94); BB-94; (2R,3S)-N4-Hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butanediamide; Batimastat

Database IDs

• CAS Number: 130370-60-4
• MDL Number: MFCD00866533
• PubChem SID: 160966956; 46505727
• PubChem CID: 5362422

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.856091
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 3.2718008
• LogD (pH = 7.4): 3.257128
• Log P: 3.2719913
• Molar Refractivity: 127.3039 cm^3
• Polarizability: 49.851807 Å^3
• Polar Surface Area: 107.53 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.23
• LOG S: -5.44
• Solubility (Water): 1.73e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Pharmacology Properties

• Target: MMP

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C23H31N3O4S2

DETAILS

DrugBank - DB03880

• Drug Groups: experimental
• Pharmacology: An anticancer drug that belongs to the family of drugs called angiogenesis inhibitors. Batimastat is a matrix metalloproteinase inhibitor.
• Affected Organisms: Humans and other mammals

Sigma Aldrich - SML0041

Biochem/physiol Actions
Batimastat is a potent, broad spectrum matrix metalloprotease (MMP) inhibitor.