(S,S)-TAPI-1 - ≥95% , CAS No.171235-71-5

CAS: 171235-71-5 Cat. No.: T275482 Formula: C₂₆H₃₇N₅O₅ Molecular Weight: 499.6 PubChem CID: 9827273

GRADE & PURITY ≥95%

Synonyms

TAPI-1 | N-[2-[2-(Hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]-3-(2-naphthalenyl)-L-alanyl-N-(2-aminoethyl)-L-alaninamide

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Product Describtion:

(S,S)-TAPI-1 is an isomer of TAPI-1. TAPI-1 is a TACE (ADAM17) inhibitor and blocks the shedding of several cell surface proteins. TAPI-1 is also a metalloproteinase (MMP) inhibitor.

Specifications

Synonyms

TAPI-1 | N-[2-[2-(Hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]-3-(2-naphthalenyl)-L-alanyl-N-(2-aminoethyl)-L-alaninamide

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Stable, selective inhibitor of TNF-α processing (IC 50 = ~100 nM).\xa0 Inhibits TACE (P< 0.01) and other metalloproteases in vivo .

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Note

Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 6 months. Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Purity

≥95%

Names and Identifiers

Pubchem Sid

504764919

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504764919

Canonical Smiles

CC(C)CC(CC(=O)NO)C(=O)NC(CC1=CC2=CC=CC=C2C=C1)C(=O)NC(C)C(=O)NCCN

IUPAC Name

N-[(2S)-1-[[(2S)-1-(2-aminoethylamino)-1-oxopropan-2-yl]amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]-N'-hydroxy-2-(2-methylpropyl)butanediamide

InChIKey

AWNBSWDIOCXWJW-OWHMDLSXSA-N

INCHI

1S/C26H37N5O5/c1-16(2)12-21(15-23(32)31-36)25(34)30-22(26(35)29-17(3)24(33)28-11-10-27)14-18-8-9-19-6-4-5-7-20(19)13-18/h4-9,13,16-17,21-22,36H,10-12,14-15,27H2,1-3H3,(H,28,33)(H,29,35)(H,30,34)(H,31,32)/t17-,21?,22-/m0/s1

Isomeric SMILES

C[C@@H](C(=O)NCCN)NC(=O)[C@H](CC1=CC2=CC=CC=C2C=C1)NC(=O)C(CC(C)C)CC(=O)NO

PubChem CID

9827273

Molecular Weight

499.6

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: N-acyl-alpha amino acids and derivatives Alpha amino acid amides Alanine and derivatives Naphthalenes N-acyl amines Secondary carboxylic acid amides Hydroxamic acids Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Alpha-dipeptide - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alanine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Naphthalene - Fatty amide - N-acyl-amine - Fatty acyl - Benzenoid - Hydroxamic acid - Carboxamide group - Amino acid or derivatives - Secondary carboxylic acid amide - Organonitrogen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Primary aliphatic amine - Organic nitrogen compound - Carbonyl group - Organooxygen compound - Primary amine - Amine - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 10 mM
• Molecular Weight: 499.600 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 499.279 Da
• Monoisotopic Mass: 499.279 Da
• Topological Polar Surface Area: 163.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 746.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 171235-71-5, the molecular formula is C26H37N5O5, and the molecular weight is 499.6 g/mol. InChIKey AWNBSWDIOCXWJW-OWHMDLSXSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.