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Showing NP-Card for [R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid (NP0062196)

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Record Information
Version2.0
Created at2022-04-28 06:51:12 UTC
Updated at2022-04-28 06:51:12 UTC
NP-MRD IDNP0062196
Secondary Accession NumbersNone
Natural Product Identification
Common Name[R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid
Description4-Amino-3-chloro-2-pentenedioic acid, also known as 3-ACPA, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. [R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid is found in Streptomyces viridogenes. [R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid was first documented in 2006 (PMID: 17151454). Based on a literature review very few articles have been published on 4-Amino-3-chloro-2-pentenedioic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)


  Mrv1652304282208512D          

 11 10  0  0  1  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  1  8  1  6  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.6440   -1.6266   -0.2924 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -0.4999    0.3810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7154    0.7346   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578    0.7018   -1.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881    1.9791    0.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718   -0.4597    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546   -1.7732    0.9152 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0263    0.5097   -0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4919    0.4715   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0793    1.4115   -1.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336   -0.5568    0.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676   -1.5010   -1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -2.3417    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -0.6382    1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6618    0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4681    1.3220   -0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.3947    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  5 15  1  0
  8 16  1  0
 11 17  1  0
M  END
Download

3D SDF for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)


  Mrv1652304282208512D          

 11 10  0  0  1  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  1  8  1  6  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](C(O)=O)C(\Cl)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6ClNO4/c6-2(1-3(8)9)4(7)5(10)11/h1,4H,7H2,(H,8,9)(H,10,11)/b2-1-/t4-/m0/s1

> <INCHI_KEY>
OZYCMBRXDKOFGB-XDSMRRFISA-N

> <FORMULA>
C5H6ClNO4

> <MOLECULAR_WEIGHT>
179.56

> <EXACT_MASS>
178.9985354

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.400768615854087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4R)-4-amino-3-chloropent-2-enedioic acid

> <ALOGPS_LOGP>
-2.88

> <JCHEM_LOGP>
-2.8925133004269776

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.5484675855912275

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4121385159527984

> <JCHEM_PKA_STRONGEST_BASIC>
7.901227096726744

> <JCHEM_POLAR_SURFACE_AREA>
100.61999999999999

> <JCHEM_REFRACTIVITY>
36.943200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R)-4-amino-3-chloropent-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)

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PDB for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    7 Cl   UNK     0       2.310  -1.334   0.000  0.00  0.00          Cl+0
HETATM    8  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.620   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    8    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)
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SMILES for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)
N[C@H](C(O)=O)C(\Cl)=C\C(O)=O
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INCHI for NP0062196 ([R-(Z)]-4-Amino-3-chloro-2-Pentenedioic acid)
InChI=1S/C5H6ClNO4/c6-2(1-3(8)9)4(7)5(10)11/h1,4H,7H2,(H,8,9)(H,10,11)/b2-1-/t4-/m0/s1
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View in JSmol
Synonyms
ValueSource
4-Amino-3-chloro-2-pentenedioateGenerator
2-Amino-3-chloro-3-pentenedioicMeSH
3-ACPAMeSH
Chemical FormulaC5H6ClNO4
Average Mass179.5600 Da
Monoisotopic Mass178.99854 Da
IUPAC Name(2Z,4R)-4-amino-3-chloropent-2-enedioic acid
Traditional Name(2Z,4R)-4-amino-3-chloropent-2-enedioic acid
CAS Registry NumberNot Available
SMILES
N[C@H](C(O)=O)C(\Cl)=C\C(O)=O
InChI Identifier
InChI=1S/C5H6ClNO4/c6-2(1-3(8)9)4(7)5(10)11/h1,4H,7H2,(H,8,9)(H,10,11)/b2-1-/t4-/m0/s1
InChI KeyOZYCMBRXDKOFGB-XDSMRRFISA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces viridogenesBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • L-alpha-amino acid
    • 

  • Amino fatty acid
    • 

  • Halogenated fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Unsaturated fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Vinylogous halide
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Vinyl chloride
    • 

  • Vinyl halide
    • 

  • Haloalkene
    • 

  • Chloroalkene
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ALOGPS
logP-2.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.41ChemAxon
pKa (Strongest Basic)7.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.94 m³·mol⁻¹ChemAxon
Polarizability14.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018573  
Chemspider ID4944256  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439877  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hutchinson RI, Grant RJ, Murphy CD: Biosynthetic origin of [R-(Z)]-4-amino-3-chloro-2-pentenedioic acid in Streptomyces viridogenes. Biosci Biotechnol Biochem. 2006 Dec;70(12):3046-9. doi: 10.1271/bbb.60372. Epub 2006 Dec 7. [PubMed:17151454  ]