AHU 377 - Moligand™, ≥98% , Neprilysin inhibitor, CAS No.149709-62-6, Neprilysin inhibitor

CAS: 149709-62-6 Cat. No.: A342776 Molecular Weight: 411.5 EC Number: 810-278-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

SACUBITRIL [ORANGE BOOK] | AHU 377 | (2R,4S)-5-biphenyl-4-yl-4-(3-carboxy-propionylamino)-2-methyl-pentanoic acid ethyl ester | (2R,4S)-5-Biphenyl-4-yl-4-(3-carboxypropionylamino)-2-methylpentanoic acid ethyl ester | 3-{[(2S,4R)-1-{[1,1'-biphenyl]-4-yl}-5

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

AHU-377 is an inhibitor of neprilysin with IC50 value of 5 nM. AHU-377 and the angiotensin II AT1 receptor antagonist valsartan compose LCZ696 in a 1:1 molar ratio. LCZ696 is an angiotensin receptor neprilysin inhibitor. It can reduce blood pressure and may be a novel drug for the treatment of heart failure. AHU-377 is a prodrug, it can be converted by enzymatic cleavage of the ethyl ester into the active form LBQ657. It is reported that AHU-377(30 and 100 mg/kg, PO) can cause antihypertensive effect in a dose-dependent manner in Dahl-SS rats. But in the DOCA-salt hypertensive rats, it shows a weak reduction.

Specifications

Synonyms

SACUBITRIL [ORANGE BOOK] | AHU 377 | (2R, 4S)-5-biphenyl-4-yl-4-(3-carboxy-propionylamino)-2-methyl-pentanoic acid ethyl ester | (2R, 4S)-5-Biphenyl-4-yl-4-(3-carboxypropionylamino)-2-methylpentanoic acid ethyl ester | 3-{[(2S, 4R)-1-{[1, 1'-biphenyl]-4-yl}-5

Specifications & Purity

Moligand™, ≥98%

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

Neprilysin inhibitor

Purity

≥98%

Product Properties

• ALogP: 3.7

Names and Identifiers

• Pubchem Sid: 488196313
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488196313
• Canonical Smiles: CCOC(=O)C(C)CC(CC1=CC=C(C=C1)C2=CC=CC=C2)NC(=O)CCC(=O)O
• IUPAC Name: 4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acid
• InChIKey: PYNXFZCZUAOOQC-UTKZUKDTSA-N
• INCHI: 1S/C24H29NO5/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28)/t17-,21+/m1/s1
• Isomeric SMILES: CCOC(=O)[C@H](C)C[C@@H](CC1=CC=C(C=C1)C2=CC=CC=C2)NC(=O)CCC(=O)O
• Molecular Weight: 411.5
• Reaxy-Rn: 14844283
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14844283&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Biphenyls and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Biphenyls and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Biphenyls and derivatives
• Alternative Parents: Gamma amino acids and derivatives Amphetamines and derivatives Fatty acid esters N-acyl amines Dicarboxylic acids and derivatives Secondary carboxylic acid amides Carboxylic acid esters Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Biphenyl - Gamma amino acid or derivatives - Amphetamine or derivatives - Fatty acid ester - Dicarboxylic acid or derivatives - Fatty amide - N-acyl-amine - Fatty acyl - Carboxylic acid ester - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid - Carboxylic acid derivative - Organonitrogen compound - Organic oxygen compound - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C 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(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Rattus norvegicus (775804 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 411.500 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 411.205 Da
• Monoisotopic Mass: 411.205 Da
• Topological Polar Surface Area: 92.700 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 550.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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