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Showing NP-Card for (2s)-2-[(hydroxymethylidene)amino]butanedioic acid (NP0296296)

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Record Information
Version2.0
Created at2022-09-10 05:47:31 UTC
Updated at2022-09-10 05:47:31 UTC
NP-MRD IDNP0296296
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-[(hydroxymethylidene)amino]butanedioic acid
DescriptionN-Formyl-L-aspartate belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. These are organic compounds containing exactly two carboxylic acid groups. N-Formyl-L-aspartate is an extremely weak basic (essentially neutral) compound (based on its pKa). (2s)-2-[(hydroxymethylidene)amino]butanedioic acid is found in Apis cerana. (2s)-2-[(hydroxymethylidene)amino]butanedioic acid was first documented in 1969 (PMID: 5823108). N-Formyl-L-aspartate exists in all living organisms, ranging from bacteria to humans (PMID: 3308850).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)


  Mrv0541 09041212462D          

 12 11  0  0  0  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  2  2  0  0  0  0
  3  6  1  6  0  0  0
  2  7  1  4  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
  3 12  1  6  0  0  0
M  END
Download

3D MOL for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
    2.7104    0.9372   -0.9202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487    0.7206    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    1.5862    1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2599   -0.4576    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0182   -0.3297   -0.3963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7749    0.8389   -0.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.0502   -0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6377    2.1824   -0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8506   -1.5272   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -1.4269    0.3570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -2.8040   -0.4120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158    2.4198    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -0.6575    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7988   -1.3423   -0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438   -0.2492   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2682    0.4172   -1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865    2.2190    0.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -3.5771    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 11  1  0
  9 10  2  0
  5 15  1  6
  4 13  1  0
  4 14  1  0
  3 12  1  0
  7 16  1  0
  8 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)


  Mrv0541 09041212462D          

 12 11  0  0  0  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  2  2  0  0  0  0
  3  6  1  6  0  0  0
  2  7  1  4  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
  3 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0296296

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO5/c7-2-6-3(5(10)11)1-4(8)9/h2-3H,1H2,(H,6,7)(H,8,9)(H,10,11)/t3-/m0/s1

> <INCHI_KEY>
MQUUQXIFCBBFDP-VKHMYHEASA-N

> <FORMULA>
C5H7NO5

> <MOLECULAR_WEIGHT>
161.1128

> <EXACT_MASS>
161.032422339

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
13.418617688514875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(hydroxymethylidene)amino]butanedioic acid

> <ALOGPS_LOGP>
-0.86

> <JCHEM_LOGP>
-0.6307712026666668

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.131482938208931

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3003553654514826

> <JCHEM_PKA_STRONGEST_BASIC>
0.8836585462270458

> <JCHEM_POLAR_SURFACE_AREA>
107.19000000000001

> <JCHEM_REFRACTIVITY>
32.0077

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-formyl-L-aspartic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)

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PDB for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)
HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    6    7                                                       
CONECT    3    1    5    6   12                                             
CONECT    4    1    8    9                                                  
CONECT    5    3   10   11                                                  
CONECT    6    2    3                                                       
CONECT    7    2                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)
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SMILES for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)
[H][C@@](CC(O)=O)(N=CO)C(O)=O
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INCHI for NP0296296 ((2s)-2-[(hydroxymethylidene)amino]butanedioic acid)
InChI=1S/C5H7NO5/c7-2-6-3(5(10)11)1-4(8)9/h2-3H,1H2,(H,6,7)(H,8,9)(H,10,11)/t3-/m0/s1
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View in JSmol
Synonyms
ValueSource
N-Formyl-L-aspartic acidGenerator
N-Formyl-L-aspartateChEBI
Chemical FormulaC5H7NO5
Average Mass161.1128 Da
Monoisotopic Mass161.03242 Da
IUPAC Name(2S)-2-[(hydroxymethylidene)amino]butanedioic acid
Traditional NameN-formyl-L-aspartic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CC(O)=O)(N=CO)C(O)=O
InChI Identifier
InChI=1S/C5H7NO5/c7-2-6-3(5(10)11)1-4(8)9/h2-3H,1H2,(H,6,7)(H,8,9)(H,10,11)/t3-/m0/s1
InChI KeyMQUUQXIFCBBFDP-VKHMYHEASA-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 Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAspartic acid and derivatives  
Alternative Parents
Substituents
  • Aspartic acid or derivatives
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Fatty acid
    • 

  • Carboximidic acid
    • 

  • Carboximidic acid derivative
    • 

  • Carboxylic acid
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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-0.86ALOGPS
logP-0.63ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)0.88ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area107.19 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.01 m³·mol⁻¹ChemAxon
Polarizability13.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060495  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID79437  
KEGG Compound IDC01044  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88052  
PDB IDNot Available
ChEBI ID48429  
Good Scents IDNot Available
References
General References
  1. Hu L, Mulfinger LM, Phillips AT: Purification and properties of formylglutamate amidohydrolase from Pseudomonas putida. J Bacteriol. 1987 Oct;169(10):4696-702. doi: 10.1128/jb.169.10.4696-4702.1987. [PubMed:3308850  ] 
  2. Scott TA, Bellion E, Mattey M: The conversion of N-formyl-L-aspartate into nicotinic acid by extracts of Clostridium butylicum. Eur J Biochem. 1969 Sep;10(2):318-23. doi: 10.1111/j.1432-1033.1969.tb00692.x. [PubMed:5823108  ] 
  3. LOTUS database [Link]