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Showing NP-Card for methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate (NP0237271)

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Record Information
Version2.0
Created at2022-09-06 20:22:04 UTC
Updated at2022-09-06 20:22:04 UTC
NP-MRD IDNP0237271
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate
DescriptionMimosine methyl ester belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate is found in Senegalia berlandieri. Based on a literature review very few articles have been published on Mimosine methyl ester.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)


  Mrv1652309062222222D          

 15 15  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
M  END
Download

3D MOL for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.2015    0.9725   -1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    0.4147   -0.3177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -0.8113   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733   -1.3548   -1.5124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -1.3525    0.8104 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4669   -0.4662    1.9356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2170   -1.7115    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030   -0.6684    0.2951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -0.4608   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492    0.5202   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065    1.3374   -0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    2.2251   -1.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    1.1387    0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2701    1.9710    1.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505    0.1367    1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0745    1.5566   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241    0.1105   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5206    1.5166   -2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -2.3107    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8286    0.4789    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021   -0.8268    2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -2.5272   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5538   -2.1425    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8310   -1.0715   -1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.6624   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8804    2.6897    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5829   -0.0267    2.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 14 26  1  0
 15 27  1  0
M  END
Download

3D SDF for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)


  Mrv1652309062222222D          

 15 15  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12N2O4/c1-15-9(14)6(10)4-11-3-2-7(12)8(13)5-11/h2-3,5-6,13H,4,10H2,1H3/t6-/m0/s1

> <INCHI_KEY>
IOYVGPITPVKNSC-LURJTMIESA-N

> <FORMULA>
C9H12N2O4

> <MOLECULAR_WEIGHT>
212.205

> <EXACT_MASS>
212.079706874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.526474297999222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoate

> <JCHEM_LOGP>
-0.5511749166666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.631361087908827

> <JCHEM_PKA_STRONGEST_BASIC>
6.912530857918504

> <JCHEM_POLAR_SURFACE_AREA>
92.86

> <JCHEM_REFRACTIVITY>
53.4273

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)

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PDB for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)
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SMILES for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)
COC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1
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INCHI for NP0237271 (methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate)
InChI=1S/C9H12N2O4/c1-15-9(14)6(10)4-11-3-2-7(12)8(13)5-11/h2-3,5-6,13H,4,10H2,1H3/t6-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H12N2O4
Average Mass212.2050 Da
Monoisotopic Mass212.07971 Da
IUPAC Namemethyl (2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoate
Traditional Namemethyl (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1
InChI Identifier
InChI=1S/C9H12N2O4/c1-15-9(14)6(10)4-11-3-2-7(12)8(13)5-11/h2-3,5-6,13H,4,10H2,1H3/t6-/m0/s1
InChI KeyIOYVGPITPVKNSC-LURJTMIESA-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
Senegalia berlandieriLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acid esters  
Alternative Parents
Substituents
  • Alpha-amino acid ester
    • 

  • Dihydropyridine
    • 

  • Hydroxypyridine
    • 

  • Hydropyridine
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Cyclic ketone
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Primary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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-0.55ChemAxon
pKa (Strongest Acidic)11.63ChemAxon
pKa (Strongest Basic)6.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.43 m³·mol⁻¹ChemAxon
Polarizability20.53 ųChemAxon
Number of Rings1ChemAxon
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 IDNot Available
Chemspider ID162325  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound186729  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]