Apstatin - Moligand™, ≥95% , Inhibitor of X-prolyl aminopeptidase 1;Inhibitor of X-prolyl aminopeptidase 2, CAS No.160470-73-5, Inhibitor of X-prolyl aminopeptidase 1;Inhibitor of X-prolyl aminopeptidase 2

CAS: 160470-73-5 Cat. No.: A335689 Molecular Weight: 459.54

GRADE & PURITY Moligand™, ≥95%

Synonyms

DTXSID30936303 | BDBM50078401 | 1n51 | UNII-JZK8P9AG86 | 1-[1-(3-Amino-2-hydroxy-4-phenylbutanoyl)prolyl]-N-(1-hydroxy-1-iminopropan-2-yl)pyrrolidine-2-carboximidic acid | N-[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTANOYL]-L-PROLYL-L-PROLYL-L-ALANINAMIDE | N

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Apstatin is a selective inhibitor of aminopeptidase P (APP), with a K|i|of 2.6 μM in rat lung membrane-bound APP. Apstatin is shown to increase Bradykinin-promoted cardioprotection in rats with artificially introduced myocardial infarctions by inhibiting the Bradykinin degradation action of APP. When combined with the angiotensin-converting enzyme inhibitors enalapril , lisinopril , or ramipril , decrease of myocardial infarction size was enhanced.

Specifications

Synonyms

DTXSID30936303 | BDBM50078401 | 1n51 | UNII-JZK8P9AG86 | 1-[1-(3-Amino-2-hydroxy-4-phenylbutanoyl)prolyl]-N-(1-hydroxy-1-iminopropan-2-yl)pyrrolidine-2-carboximidic acid | N-[(2S, 3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTANOYL]-L-PROLYL-L-PROLYL-L-ALANINAMIDE | N

Specifications & Purity

Moligand™, ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of X-prolyl aminopeptidase 1;Inhibitor of X-prolyl aminopeptidase 2

Purity

≥95%

Product Properties

• Ki Data: Aminopeptidase P (APP): Ki= 2.6 μM (rat)

Names and Identifiers

• Canonical Smiles: CC(C(=O)N)NC(=O)C1CCCN1C(=O)C2CCCN2C(=O)C(C(CC3=CC=CC=C3)N)O
• IUPAC Name: (2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carbonyl]-N-[(2S)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
• InChIKey: YVUUZAPYLPWFHE-HXFGRODQSA-N
• INCHI: 1S/C23H33N5O5/c1-14(20(25)30)26-21(31)17-9-5-11-27(17)22(32)18-10-6-12-28(18)23(33)19(29)16(24)13-15-7-3-2-4-8-15/h2-4,7-8,14,16-19,29H,5-6,9-13,24H2,1H3,(H2,25,30)(H,26,31)/t14-,16+,17-,18-,19-/m0/s1
• Isomeric SMILES: C[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)[C@H]([C@@H](CC3=CC=CC=C3)N)O
• WGK Germany: 3
• Alternate CAS: 160470-73-5
• MeSH Entry Terms: apstatin;N-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-prolyl-L-prolyl-L-alaninamide
• Molecular Weight: 459.54
• Reaxy-Rn: 8660998
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8660998&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Hybrid peptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Hybrid peptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Hybrid peptides
• Alternative Parents: N-acyl-alpha amino acids and derivatives Proline and derivatives Alpha amino acid amides Alanine and derivatives Beta amino acids and derivatives Amphetamines and derivatives Pyrrolidinecarboxamides N-acylpyrrolidines Aralkylamines Monosaccharides Tertiary carboxylic acid amides Secondary alcohols Primary carboxylic acid amides Secondary carboxylic acid amides Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hybrid peptide - Proline or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alanine or derivatives - Beta amino acid or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - N-acylpyrrolidine - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-2-carboxamide - Aralkylamine - Monocyclic benzene moiety - Monosaccharide - Benzenoid - Tertiary carboxylic acid amide - Pyrrolidine - Secondary alcohol - Primary carboxylic acid amide - Secondary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organic nitrogen compound - Primary aliphatic amine - Amine - Carbonyl group - Hydrocarbon derivative - Alcohol - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through 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

Associated Targets(Human)

LAP3 Tchem Cytosol aminopeptidase (1 Activities)

Discover Target: LAP3

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

XPNPEP1 Tchem Xaa-Pro aminopeptidase 1 (1 Activities)

Discover Target: XPNPEP1

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

XPNPEP2 Tchem Xaa-Pro aminopeptidase 2 (2 Activities)

Discover Target: XPNPEP2

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

XPNPEP1 Tchem Xaa-Pro aminopeptidase 1 (90 Activities)

Discover Target: XPNPEP1

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

PEPD Tchem Xaa-Pro dipeptidase (89 Activities)

Discover Target: PEPD

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

XPNPEP2 Tchem Xaa-Pro aminopeptidase 2 (41 Activities)

Discover Target: XPNPEP2

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (>25 mg/ml), and DMSO (20 mg/ml).
• Refractive Index: n20D1.61
• Boil Point(°C): ~864.3° C at 760 mmHg (Predicted)
• Melt Point(°C): 327.91° C (Predicted)
• Molecular Weight: 459.500 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 459.248 Da
• Monoisotopic Mass: 459.248 Da
• Topological Polar Surface Area: 159.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 741.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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