Batimastat - Moligand™, 10mM in DMSO , Inhibitor of MMP1;Inhibitor of MMP13;Inhibitor of MMP3, CAS No.130370-60-4, Inhibitor of MMP1;Inhibitor of MMP13;Inhibitor of MMP3

CAS: 130370-60-4 Cat. No.: B421183 Molecular Weight: 477.64 EC Number: 694-664-4

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

Butanediamide, N(sup 4)-hydroxy-N(sup 1)-(2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl)-2-(2-methylpropyl)-3-((2-thienylthio)methyl)-, (2R-(1(S*),2R*,3S*))- | batimastatum | (2R,3S)-N~1~-[(1S)-1-benzyl-2-(methylamino)-2-oxoethyl]-N~4~-hydroxy-2-(2-methylpr

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Batimastat is a potent broad spectrum MMP inhibitor with IC50 of 3, 4, 4, 6, and 20 nM for MMP-1, MMP-2, MMP-9, MMP-7 and MMP-3, respectively.
Batimastat was used to study the role of MMP in proteolytic release of EGF in human follicular thyroid carcinoma cell line FTC-133.

Specifications

Synonyms

Butanediamide, N(sup 4)-hydroxy-N(sup 1)-(2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl)-2-(2-methylpropyl)-3-((2-thienylthio)methyl)-, (2R-(1(S*), 2R*, 3S*))- | batimastatum | (2R, 3S)-N~1~-[(1S)-1-benzyl-2-(methylamino)-2-oxoethyl]-N~4~-hydroxy-2-(2-methylpr

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Batimastat is a potent, broad spectrum matrix metalloprotease (MMP) inhibitor. Batimastat is hydroxamate-type inhibitor of matrix metalloproteinases (MMP).It inhibits the growth and spread of lung tumors, breast cancer regrowth and human colon tumor growth

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of MMP1;Inhibitor of MMP13;Inhibitor of MMP3

Names and Identifiers

• Canonical Smiles: CC(C)CC(C(CSC1=CC=CS1)C(=O)NO)C(=O)NC(CC2=CC=CC=C2)C(=O)NC
• IUPAC Name: (2S,3R)-N-hydroxy-N'-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide
• InChIKey: XFILPEOLDIKJHX-QYZOEREBSA-N
• 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
• Isomeric SMILES: CC(C)C[C@H]([C@H](CSC1=CC=CS1)C(=O)NO)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)NC
• WGK Germany: 3
• Molecular Weight: 477.64
• Reaxy-Rn: 24715439
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24715439&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Phenylalanine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Phenylalanine and derivatives
• Alternative Parents: N-acyl-alpha amino acids and derivatives Alpha amino acid amides Amphetamines and derivatives Alkylarylthioethers N-acyl amines Thiophenes Heteroaromatic compounds Secondary carboxylic acid amides Hydroxamic acids Sulfenyl compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenylalanine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Amphetamine or derivatives - Aryl thioether - Alkylarylthioether - Monocyclic benzene moiety - Fatty amide - N-acyl-amine - Fatty acyl - Benzenoid - Heteroaromatic compound - Thiophene - Carboxamide group - Hydroxamic acid - Secondary carboxylic acid amide - Organoheterocyclic compound - Thioether - Sulfenyl compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

FCER2 Tchem Low affinity immunoglobulin epsilon Fc receptor (2 Activities)

Discover Target: FCER2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP1 Tchem Interstitial collagenase (8 Activities)

Discover Target: MMP1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP7 Tchem Matrilysin (2 Activities)

Discover Target: MMP7

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP13 Tchem Collagenase 3 (1 Activities)

Discover Target: MMP13

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP14 Tchem Matrix metalloproteinase-14 (4 Activities)

Discover Target: MMP14

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP9 Tchem Matrix metalloproteinase-9 (4 Activities)

Discover Target: MMP9

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP2 Tchem 72 kDa type IV collagenase (6 Activities)

Discover Target: MMP2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ADAM17 Tchem Disintegrin and metalloproteinase domain-containing protein 17 (2 Activities)

Discover Target: ADAM17

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP3 Tchem Stromelysin-1 (5 Activities)

Discover Target: MMP3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ANPEP Tchem Aminopeptidase N (863 Activities)

Discover Target: ANPEP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FCER2 Tchem Immunoglobulin epsilon Fc receptor (92 Activities)

Discover Target: FCER2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BMP1 Tchem Bone morphogenetic protein 1 (1282 Activities)

Discover Target: BMP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC8 Tclin Histone deacetylase 8 (4516 Activities)

Discover Target: HDAC8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

Discover Target: MMP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)

Discover Target: MMP8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP14 Tchem Matrix metalloproteinase 14 (1592 Activities)

Discover Target: MMP14

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC3 Tclin Histone deacetylase 3 (3654 Activities)

Discover Target: HDAC3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LAP3 Tchem Leucine aminopeptidase (179 Activities)

Discover Target: LAP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP7 Tchem Matrix metalloproteinase 7 (1073 Activities)

Discover Target: MMP7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)

Discover Target: MMP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mmp13 Matrix metalloproteinase 13 (19 Activities)

Discover Target: Mmp13

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Adam17 ADAM17 (14 Activities)

Discover Target: Adam17

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp2 Matrix metalloproteinase-2 (12 Activities)

Discover Target: Mmp2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

Discover Target: Mmp9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Snake venom metalloproteinase Bap1 (31 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 477.600 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 477.176 Da
• Monoisotopic Mass: 477.176 Da
• Topological Polar Surface Area: 161.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 614.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhao Qu, Yushan Lin, Daniel Kam-Wah Mok, Qingya Bian, William Chi-Shing Tai, Sibao Chen.  (2020)  Arnicolide D Inhibits Triple Negative Breast Cancer Cell Proliferation by Suppression of Akt/mTOR and STAT3 Signaling Pathways.  International Journal of Medical Sciences,      [PMID:32669950] [10.7150/ijms.46925]