(2S,3R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-N',2-dihydroxy-3-(2-methylpropyl)butanediamide

• ChemBase ID: 665
• Molecular Formular: C15H29N3O5
• Molecular Mass: 331.40786
• Monoisotopic Mass: 331.21072104
• SMILES: O[C@@H]([C@@H](CC(C)C)C(=O)N[C@@H](C(C)(C)C)C(=O)NC)C(=O)NO
• Canonical SMILES: ONC(=O)[C@H]([C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)NC)CC(C)C)O
• InChI: InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1
• InChIKey: OCSMOTCMPXTDND-OUAUKWLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-N',2-dihydroxy-3-(2-methylpropyl)butanediamide
• IUPAC Traditional name: @marimastat; marimastat
• Brand Name: Marimastat [Usan]
• Synonyms: marimastat; Marimastat; BB2516, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl] propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide; Marimastat

Database IDs

• CAS Number: 154039-60-8
• MDL Number: MFCD00866242
• PubChem SID: 46505547; 160964128
• PubChem CID: 119031

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.611082
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -0.059247203
• LogD (pH = 7.4): -0.08470642
• Log P: -0.058912538
• Molar Refractivity: 84.1971 cm^3
• Polarizability: 33.326736 Å^3
• Polar Surface Area: 127.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.41
• LOG S: -1.99
• Solubility (Water): 3.38e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: solid
• Hydrophobicity(logP): 0.4

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C15H29N3O5

DETAILS

DrugBank - DB00786

• Drug Groups: approved; investigational
• Description: Used in the treatment of cancer, Marmiastat is an angiogenesis and metastasis inhibitor. As an angiogenesis inhibitor it limits the growth and production of blood vessels. As an antimetatstatic agent it prevents malignant cells from breaching the basement membranes.
• Indication: For the treatment of various cancers
• Pharmacology: Used in the treatment of cancer, it is an angiogenesis and metastasis inhibitor. As an angiogenesis inhibitor it limits the growth and production of blood vessels. As an antimetatstatic agent it prevents malignant cells from breaching the basement membranes.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - M2699

Biochem/physiol Actions
Marimastat is a broad spectrum matrix metalloprotease (MMP) inhibitor