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Showing NP-Card for (2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid (NP0251646)

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Record Information
Version2.0
Created at2022-09-07 14:54:01 UTC
Updated at2022-09-07 14:54:01 UTC
NP-MRD IDNP0251646
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid
Description4-Chlorothreonine belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. (2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid was first documented in 2004 (PMID: 15196052). Based on a literature review a small amount of articles have been published on 4-Chlorothreonine (PMID: 29495881) (PMID: 28704585) (PMID: 23025743) (PMID: 17254950).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)


  Mrv1652309072216542D          

  9  8  0  0  1  0            999 V2000
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    1.0030    0.0430    1.4682 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4168    0.6884    0.3232 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1845    0.4921   -0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030    0.9894   -1.9938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3481   -0.2497   -0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    0.3629    0.1620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5424    1.0091   -0.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3090   -1.1175    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4911   -1.8657   -1.3083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    0.5662    1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832   -0.9486    1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    1.7974    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4213   -1.2394   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592    0.7260    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623    1.6278   -0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -1.6468    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -1.2347   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  6 14  1  1
  7 15  1  0
  8 16  1  0
  8 17  1  0
  5 13  1  0
M  END
Download

3D SDF for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)


  Mrv1652309072216542D          

  9  8  0  0  1  0            999 V2000
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251646

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8ClNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m0/s1

> <INCHI_KEY>
CETUIFTXYGHITB-STHAYSLISA-N

> <FORMULA>
C4H8ClNO3

> <MOLECULAR_WEIGHT>
153.56

> <EXACT_MASS>
153.0192708

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.266192337925784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-amino-4-chloro-3-hydroxybutanoic acid

> <JCHEM_LOGP>
-3.1637690068671005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.802147355113025

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7297420816822404

> <JCHEM_PKA_STRONGEST_BASIC>
8.957494652245662

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
31.054499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-amino-4-chloro-3-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)

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PDB for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  N   UNK     0       2.310  -0.206   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       6.311   2.104   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)
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SMILES for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)
N[C@H]([C@@H](O)CCl)C(O)=O
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INCHI for NP0251646 ((2r,3r)-2-amino-4-chloro-3-hydroxybutanoic acid)
InChI=1S/C4H8ClNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC4H8ClNO3
Average Mass153.5600 Da
Monoisotopic Mass153.01927 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
N[C@H]([C@@H](O)CCl)C(O)=O
InChI Identifier
InChI=1S/C4H8ClNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m0/s1
InChI KeyCETUIFTXYGHITB-STHAYSLISA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentD-alpha-amino acids  
Alternative Parents
Substituents
  • D-alpha-amino acid
    • 

  • Beta-hydroxy acid
    • 

  • Halogenated fatty acid
    • 

  • Short-chain hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Hydroxy acid
    • 

  • Chlorohydrin
    • 

  • Amino acid
    • 

  • Halohydrin
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organohalogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • Organochloride
    • 

  • Organonitrogen compound
    • 

  • 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58808116  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71355953  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dong M, Cao P, Ma YT, Luo J, Yan Y, Li RT, Huang SX: A new actinomycin Z analogue with an additional oxygen bridge between chromophore and beta-depsipentapeptide from Streptomyces sp. KIB-H714. Nat Prod Res. 2019 Jan;33(2):219-225. doi: 10.1080/14786419.2018.1443097. Epub  2018 Mar 2. [PubMed:29495881  ] 
  2. Scaglione A, Fullone MR, Montemiglio LC, Parisi G, Zamparelli C, Vallone B, Savino C, Grgurina I: Structure of the adenylation domain Thr1 involved in the biosynthesis of 4-chlorothreonine in Streptomyces sp. OH-5093-protein flexibility and molecular bases of substrate specificity. FEBS J. 2017 Sep;284(18):2981-2999. doi: 10.1111/febs.14163. Epub 2017 Aug 7. [PubMed:28704585  ] 
  3. Fullone MR, Paiardini A, Miele R, Marsango S, Gross DC, Omura S, Ros-Herrera E, Bonaccorsi di Patti MC, Lagana A, Pascarella S, Grgurina I: Insight into the structure-function relationship of the nonheme iron halogenases involved in the biosynthesis of 4-chlorothreonine --Thr3 from Streptomyces sp. OH-5093 and SyrB2 from Pseudomonas syringae pv. syringae B301DR. FEBS J. 2012 Dec;279(23):4269-82. doi: 10.1111/febs.12017. Epub 2012 Oct 30. [PubMed:23025743  ] 
  4. Singh GM, Vaillancourt FH, Yin J, Walsh CT: Characterization of SyrC, an aminoacyltransferase shuttling threonyl and chlorothreonyl residues in the syringomycin biosynthetic assembly line. Chem Biol. 2007 Jan;14(1):31-40. doi: 10.1016/j.chembiol.2006.11.005. [PubMed:17254950  ] 
  5. Scaloni A, Dalla Serra M, Amodeo P, Mannina L, Vitale RM, Segre AL, Cruciani O, Lodovichetti F, Greco ML, Fiore A, Gallo M, D'Ambrosio C, Coraiola M, Menestrina G, Graniti A, Fogliano V: Structure, conformation and biological activity of a novel lipodepsipeptide from Pseudomonas corrugata: cormycin A. Biochem J. 2004 Nov 15;384(Pt 1):25-36. doi: 10.1042/BJ20040422. [PubMed:15196052  ] 
  6. LOTUS database [Link]