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Apstatin - ≥95%, high purity , CAS No.160470-73-5, Inhibitor of X-prolyl aminopeptidase 1;Inhibitor of X-prolyl aminopeptidase 2
a selective inhibitor of Aminopeptidase P (APP)
Basic Description
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 Temp
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
Product Description
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.
Taxonomic Classification
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.
Product Properties
Ki Data
Aminopeptidase P (APP): Ki= 2.6 μM (rat)
Associated Targets(Human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
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
INCHI
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
InChIKey
YVUUZAPYLPWFHE-HXFGRODQSA-N
Smiles
CC(C(=O)N)NC(=O)C1CCCN1C(=O)C2CCCN2C(=O)C(C(CC3=CC=CC=C3)N)O
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=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
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
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