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Showing NP-Card for Isopyridoxal (NP0087171)

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Record Information
Version2.0
Created at2022-05-11 16:42:06 UTC
Updated at2022-05-11 16:42:06 UTC
NP-MRD IDNP0087171
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsopyridoxal
DescriptionIsopyridoxal belongs to the class of organic compounds known as pyridine carboxaldehydes. These are aromatic compounds containing a pyridine ring which bears a carboxaldehyde group. A pyridinecarbaldehyde that is pyridine-5-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 4 respectively. Isopyridoxal is found in Daphnia pulex and Trypanosoma brucei. Isopyridoxal was first documented in 1961 (PMID: 13702476). Isopyridoxal is a strong basic compound (based on its pKa) (PMID: 2208740).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087171 (Isopyridoxal)


  Mrv0541 02231219552D          

 12 12  0  0  0  0            999 V2000
   23.1990  -13.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4873  -13.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5726  -11.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0493  -11.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8126  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2865  -11.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9865  -11.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4616  -11.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0513  -12.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2271  -12.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8117  -11.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2239  -11.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  9  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  2  0  0  0  0
  4 12  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  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
M  END
Download

3D MOL for NP0087171 (Isopyridoxal)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.9981    0.4385   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    0.6602   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    1.8724    0.2097 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    2.0641    0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902    1.0019    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201    1.2508    0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    0.3384    0.2729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123   -0.2603   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -1.4278   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911   -2.5859   -0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -0.3968   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1364   -1.6519   -0.4478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587    1.3530    0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3173   -0.3469    0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    0.0783   -1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    3.0594    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006    2.2396    0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927   -1.5900    0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3679   -1.2766   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049   -3.0343    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323   -1.7858   -0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  6 17  1  0
  9 18  1  0
  9 19  1  0
 10 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0087171 (Isopyridoxal)


  Mrv0541 02231219552D          

 12 12  0  0  0  0            999 V2000
   23.1990  -13.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4873  -13.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5726  -11.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0493  -11.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8126  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2865  -11.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9865  -11.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4616  -11.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0513  -12.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2271  -12.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8117  -11.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2239  -11.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  9  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  2  0  0  0  0
  4 12  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  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
M  END
> <DATABASE_ID>
NP0087171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=NC=C(C=O)C(CO)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2-3,11-12H,4H2,1H3

> <INCHI_KEY>
GNKXHPULSPWUAK-UHFFFAOYSA-N

> <FORMULA>
C8H9NO3

> <MOLECULAR_WEIGHT>
167.162

> <EXACT_MASS>
167.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.288363560559585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-4-(hydroxymethyl)-6-methylpyridine-3-carbaldehyde

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
-0.47146918633333307

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.671856362300794

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.024199046676518

> <JCHEM_PKA_STRONGEST_BASIC>
4.779660957525114

> <JCHEM_POLAR_SURFACE_AREA>
70.42

> <JCHEM_REFRACTIVITY>
43.873400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopyridoxal

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087171 (Isopyridoxal)

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PDB for NP0087171 (Isopyridoxal)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      43.305 -26.100   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.710 -24.718   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      40.269 -20.740   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      44.892 -20.745   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      42.584 -24.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      47.201 -22.066   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.041 -22.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.662 -22.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.896 -23.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.357 -23.420   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.582 -22.084   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.351 -20.745   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    9                                                            
CONECT    3    7                                                            
CONECT    4    8   12                                                       
CONECT    5    1   10                                                       
CONECT    6    8                                                            
CONECT    7    3   11                                                       
CONECT    8    4    6    9                                                  
CONECT    9    2    8   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    7   10   12                                                  
CONECT   12    4   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0087171 (Isopyridoxal)
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SMILES for NP0087171 (Isopyridoxal)
CC1=NC=C(C=O)C(CO)=C1O
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INCHI for NP0087171 (Isopyridoxal)
InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2-3,11-12H,4H2,1H3
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View in JSmol
Synonyms
ValueSource
5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridinecarboxaldehydeHMDB
5-Hydroxy-4-(hydroxymethyl)-6-methyl-nicotinaldehydeHMDB
5-Hydroxy-4-(hydroxymethyl)-6-methylpyridine-3-carbaldehydeHMDB
Chemical FormulaC8H9NO3
Average Mass167.1620 Da
Monoisotopic Mass167.05824 Da
IUPAC Name5-hydroxy-4-(hydroxymethyl)-6-methylpyridine-3-carbaldehyde
Traditional Nameisopyridoxal
CAS Registry NumberNot Available
SMILES
CC1=NC=C(C=O)C(CO)=C1O
InChI Identifier
InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2-3,11-12H,4H2,1H3
InChI KeyGNKXHPULSPWUAK-UHFFFAOYSA-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridine carboxaldehydes. These are aromatic compounds containing a pyridine ring which bears a carboxaldehyde group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassPyridine carboxaldehydes  
Direct ParentPyridine carboxaldehydes  
Alternative Parents
Substituents
  • 3-pyridine carboxaldehyde
    • 

  • Aryl-aldehyde
    • 

  • Hydroxypyridine
    • 

  • Methylpyridine
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Aromatic alcohol
    • 

  • Organic nitrogen compound
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aldehyde
    • 

  • Organic oxide
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP0.04ALOGPS
logP-0.47ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.02ChemAxon
pKa (Strongest Basic)4.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.42 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.87 m³·mol⁻¹ChemAxon
Polarizability16.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004290  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023359  
KNApSAcK IDNot Available
Chemspider ID389729  
KEGG Compound IDC06051  
BioCyc IDCPD-383  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7046  
PubChem Compound440899  
PDB IDNot Available
ChEBI ID17889  
Good Scents IDNot Available
References
General References
  1. Edwards P, Liu PK, Rose GA: Liquid chromatographic studies of vitamin B6 metabolism in man. Clin Chim Acta. 1990 Sep;190(1-2):67-80. doi: 10.1016/0009-8981(90)90281-v. [PubMed:2208740  ] 
  2. FUJIOKA M, MORINO Y, SAKAMOTO Y: Enzymatic studies on pyridoxine metabolism. V. Enzymatic reduction of isopyridoxal. J Biochem. 1961 Apr;49:333-8. doi: 10.1093/oxfordjournals.jbchem.a127303. [PubMed:13702476  ]