An official website of the United States government

N-(5-Guanidino-1-((4-nitrophenyl)amino)-1-oxopentan-2-yl)benzamide hydrochloride

PubChem CID
2724371
Structure
N-(5-Guanidino-1-((4-nitrophenyl)amino)-1-oxopentan-2-yl)benzamide hydrochloride_small.png
N-(5-Guanidino-1-((4-nitrophenyl)amino)-1-oxopentan-2-yl)benzamide hydrochloride_3D_Structure.png
Molecular Formula
Synonyms
  • 911-77-3
  • BAPNA
  • N-(5-Guanidino-1-((4-nitrophenyl)amino)-1-oxopentan-2-yl)benzamide hydrochloride
  • N-Benzoyl-DL-arginine-4-nitroanilide hydrochloride
  • Bz-DL-Arg-pNA HCl
Molecular Weight
434.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
A chromogenic substrate that permits direct measurement of peptide hydrolase activity, e.g., papain and trypsin, by colorimetry. The substrate liberates p-nitroaniline as a chromogenic product.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-(5-Guanidino-1-((4-nitrophenyl)amino)-1-oxopentan-2-yl)benzamide hydrochloride.png

1.2 3D Conformer

3D Conformer of Parent

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Bz-DL-Arg-pNA.HCl
Sequence
R

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

N-[5-(diaminomethylideneamino)-1-(4-nitroanilino)-1-oxopentan-2-yl]benzamide;hydrochloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C19H22N6O4.ClH/c20-19(21)22-12-4-7-16(24-17(26)13-5-2-1-3-6-13)18(27)23-14-8-10-15(11-9-14)25(28)29;/h1-3,5-6,8-11,16H,4,7,12H2,(H,23,27)(H,24,26)(H4,20,21,22);1H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

DEOKFPFLXFNAON-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1=CC=C(C=C1)C(=O)NC(CCCN=C(N)N)C(=O)NC2=CC=C(C=C2)[N+](=O)[O-].Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C19H23ClN6O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 Deprecated CAS

37039-24-0, 99671-52-0

3.3.3 ChEMBL ID

3.3.4 DSSTox Substance ID

3.3.5 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • BAPNA
  • Benzoylarginine Nitroanilide
  • Benzoylarginine Nitroanilide Monohydrochloride
  • Benzoylarginine Nitroanilide, (R)-Isomer
  • Benzoylarginine Nitroanilide, (S)-Isomer
  • Benzoylarginine Nitroanilide, Monosodium Salt, Monohydrochloride
  • Monohydrochloride, Benzoylarginine Nitroanilide
  • N alpha Benzoyl DL arginine 4 nitroanilide
  • N Benzoylarginine 4 nitroanilide
  • N Benzoylarginyl 4 nitroanilide
  • N-alpha-Benzoyl-DL-arginine-4-nitroanilide
  • N-Benzoylarginine-4-nitroanilide
  • N-Benzoylarginyl-4-nitroanilide
  • Nitroanilide, Benzoylarginine

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
434.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
434.1469309 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
434.1469309 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
168 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
588
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

1 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.2 IR Spectra

5.2.1 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Inc.
Catalog Number
85,711-4
Lot Number
03717JP
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company LLC
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/sigma/B4875>B4875</a>
Lot Number
110H0329
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.3 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/aldrich/857114>857114</a>
Lot Number
03717JP
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company LLC
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/sigma/B4875>B4875</a>
Lot Number
110H0329
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Chromogenic Compounds
Colorless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into colored compounds; used in biochemical assays and in diagnosis as indicators, especially in the form of enzyme substrates. Synonym: chromogens (not to be confused with pigment-synthesizing bacteria also called chromogens). (See all compounds classified as Chromogenic Compounds.)

9 Use and Manufacturing

9.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzamide, N-[4-[(aminoiminomethyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]-, hydrochloride (1:1): INACTIVE

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 EPA DSSTox Classification

13.3 EPA TSCA and CDR Classification

13.4 EPA Substance Registry Services Tree

13.5 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    N-α-Benzoyl-DL-arginine-p-nitroanilide hydrochloride
    https://commonchemistry.cas.org/detail?cas_rn=911-77-3
  2. EPA Chemicals under the TSCA
    Benzamide, N-[4-[(aminoiminomethyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]-, hydrochloride (1:1)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  3. EPA DSSTox
    Benzamide, N-[4-[(aminoiminomethyl)amino]-1-[[(4-nitrophenyl)amino]carbonyl]butyl]-, hydrochloride (1:1)
    https://comptox.epa.gov/dashboard/DTXSID50883603
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  5. SpectraBase
    N alpha-Benzoyl-DL-arginine-4-nitroanilide HCl
    https://spectrabase.com/spectrum/AJ1RR0NWeD4
    Nα-Benzoyl-DL-arginine p-nitroanilide hydrochloride
    https://spectrabase.com/spectrum/4Z4QXWX4FQC
    DL-N-{4-GUANIDINO-1-[(p-NITROPHENYL)CARBAMOYL]BUTYL}BENZAMIDE,MONOHYDROCHLORIDE
    https://spectrabase.com/spectrum/8yrPOlkEv8K
    L-N-{4-GUANIDINO-1-[(p-NITROPHENYL)CARBAMOYL]BUTYL}BENZAMIDE,MONOHYDROCHLORIDE
    https://spectrabase.com/spectrum/8GPA9w3iI9o
    N alpha-Benzoyl-DL-arginine-4-nitroanilide HCl
    https://spectrabase.com/spectrum/BQykRRGUhwM
    Nα-Benzoyl-DL-arginine p-nitroanilide hydrochloride
    https://spectrabase.com/spectrum/IiwrOLJVBtP
  6. Wikidata
    N-Benzoyl-DL-arginine-4-nitroanilide hydrochloride
    https://www.wikidata.org/wiki/Q72440200
  7. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Benzoylarginine Nitroanilide
    https://www.ncbi.nlm.nih.gov/mesh/68001586
  8. PubChem
  9. EPA Substance Registry Services
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  11. PATENTSCOPE (WIPO)
CONTENTS