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Showing metabocard for Nudifloramide (HMDB0004193)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 13:56:50 UTC
Update Date2023-07-07 20:53:58 UTC
HMDB IDHMDB0004193
Secondary Accession Numbers
  • HMDB04193
Metabolite Identification
Common NameNudifloramide
DescriptionN-methyl-2-pyridone-5-carboxamide (2PY) is one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation. Increased serum 2PY concentrations are observed in chronic renal failure (CRF) patients, which along with the deterioration of kidney function and its toxic properties (significant inhibition of PARP-1), suggests that 2PY is an uremic toxin. (PMID 12694300 ). 2PY has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1676999817
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004193 (Nudifloramide)

  Mrv0541 02231219542D          

 11 11  0  0  0  0            999 V2000
   21.5656  -24.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9932  -25.4339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8512  -22.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4223  -25.4339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4223  -26.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8512  -23.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7077  -25.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1367  -24.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1367  -25.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7077  -24.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4223  -23.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for HMDB0004193 (Nudifloramide)

HMDB0004193
     RDKit          3D
N1-Methyl-2-pyridone-5-carboxamide
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.3303   -0.8583    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902   -0.0883    0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054   -0.4275    0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0251    0.2701   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -0.1512   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880   -1.2963    0.6452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3454    0.4715   -0.6945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    1.3696   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    1.7617   -1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964    0.9930   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    1.3132   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -1.3744    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336   -1.5513    1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694   -0.2046    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482   -1.2997    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357   -1.3809    1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498   -2.1131    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    1.9303   -1.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    2.6359   -1.7879 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
M  END
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3D SDF for HMDB0004193 (Nudifloramide)

  Mrv0541 02231219542D          

 11 11  0  0  0  0            999 V2000
   21.5656  -24.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9932  -25.4339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8512  -22.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4223  -25.4339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4223  -26.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8512  -23.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7077  -25.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1367  -24.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1367  -25.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7077  -24.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4223  -23.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004193

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=C(C=CC1=O)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N2O2/c1-9-4-5(7(8)11)2-3-6(9)10/h2-4H,1H3,(H2,8,11)

> <INCHI_KEY>
JLQSXXWTCJPCBC-UHFFFAOYSA-N

> <FORMULA>
C7H8N2O2

> <MOLECULAR_WEIGHT>
152.1506

> <EXACT_MASS>
152.05857751

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.712395231777144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-1.1313507759999997

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.931644734648511

> <JCHEM_PKA_STRONGEST_BASIC>
1.363377223060129

> <JCHEM_POLAR_SURFACE_AREA>
63.4

> <JCHEM_REFRACTIVITY>
40.763400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-6-oxopyridine-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0004193 (Nudifloramide)

HMDB0004193
     RDKit          3D
N1-Methyl-2-pyridone-5-carboxamide
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.3303   -0.8583    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902   -0.0883    0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054   -0.4275    0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0251    0.2701   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -0.1512   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880   -1.2963    0.6452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3454    0.4715   -0.6945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    1.3696   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    1.7617   -1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964    0.9930   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    1.3132   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -1.3744    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336   -1.5513    1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694   -0.2046    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482   -1.2997    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357   -1.3809    1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498   -2.1131    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    1.9303   -1.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    2.6359   -1.7879 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

PDB for HMDB0004193 (Nudifloramide)

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      40.256 -45.167   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      33.587 -47.477   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      38.922 -42.856   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      36.255 -47.477   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      36.255 -49.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.922 -44.397   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.921 -46.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.589 -45.167   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.589 -46.707   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.921 -45.167   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.255 -44.397   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    5    7    9                                                  
CONECT    5    4                                                            
CONECT    6    1    3    8                                                  
CONECT    7    2    4   10                                                  
CONECT    8    6    9   11                                                  
CONECT    9    4    8                                                       
CONECT   10    7   11                                                       
CONECT   11    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0004193 (Nudifloramide)

COMPND    HMDB0004193
HETATM    1  C1  UNL     1      -2.330  -0.858   0.871  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.290  -0.088   0.207  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.005  -0.427   0.311  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.025   0.270  -0.300  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.410  -0.151  -0.147  1.00  0.00           C  
HETATM    6  N2  UNL     1       2.688  -1.296   0.645  1.00  0.00           N  
HETATM    7  O1  UNL     1       3.345   0.472  -0.694  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.664   1.370  -1.050  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.658   1.762  -1.189  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.596   0.993  -0.537  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.810   1.313  -0.636  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.891  -1.374   0.054  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.834  -1.551   1.565  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.069  -0.205   1.375  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.248  -1.300   0.911  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.336  -1.381   1.631  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.250  -2.113   0.307  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.436   1.930  -1.536  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.927   2.636  -1.788  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   10
CONECT    3    4    4   15
CONECT    4    5    8
CONECT    5    6    7    7
CONECT    6   16   17
CONECT    8    9    9   18
CONECT    9   10   19
CONECT   10   11   11
END
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SMILES for HMDB0004193 (Nudifloramide)

CN1C=C(C=CC1=O)C(N)=O
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INCHI for HMDB0004193 (Nudifloramide)

InChI=1S/C7H8N2O2/c1-9-4-5(7(8)11)2-3-6(9)10/h2-4H,1H3,(H2,8,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Methyl-5-carboxylamide-2-pyridoneChEBI
N'-methyl-2-pyridone-5-carboxamideChEBI
N(1)-Methyl-2-pyridone-5-carboxamideChEBI
N-Methyl-2-pyridone-5-carboxamideChEBI
N'Methyl-2-pyridone-5-carboxamideHMDB
Chemical FormulaC7H8N2O2
Average Molecular Weight152.1506
Monoisotopic Molecular Weight152.05857751
IUPAC Name1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide
Traditional Name1-methyl-6-oxopyridine-3-carboxamide
CAS Registry Number701-44-0
SMILES
CN1C=C(C=CC1=O)C(N)=O
InChI Identifier
InChI=1S/C7H8N2O2/c1-9-4-5(7(8)11)2-3-6(9)10/h2-4H,1H3,(H2,8,11)
InChI KeyJLQSXXWTCJPCBC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Dihydropyridinecarboxylic acid derivative
  • Nicotinamide
  • Dihydropyridine
  • Pyridinone
  • Hydropyridine
  • Heteroaromatic compound
  • Lactam
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos132.0730932474
[M+H]+Not Available132.092http://allccs.zhulab.cn/database/detail?ID=AllCCS00000477
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified51.27 +/- 23.66 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified41.00 (16.00-66.00) umol/mmol creatinineAdult (>18 years old)BothPellagra details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Pellagra
  1. Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [PubMed:17709435 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023330
KNApSAcK IDNot Available
Chemspider ID62899
KEGG Compound IDC05842
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN1-Methyl-2-pyridone-5-carboxamide
METLIN ID7025
PubChem Compound69698
PDB IDNot Available
ChEBI ID27410
Food Biomarker OntologyNot Available
VMH IDM02505
MarkerDB IDMDB00000442
Good Scents IDNot Available
References
Synthesis ReferenceGrudzinski, Stefan. Preparation of N-methyl-2-pyridone-5-carboxamide. Roczniki Chemii (1962), 36 1705-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Carter EG: Quantitation of urinary niacin metabolites by reversed-phase liquid chromatography. Am J Clin Nutr. 1982 Nov;36(5):926-30. [PubMed:6215856 ]
  2. Patterson JI, Brown RR, Linkswiler H, Harper AE: Excretion of tryptophan-niacin metabolites by young men: effects of tryptophan, leucine, and vitamin B6 intakes. Am J Clin Nutr. 1980 Oct;33(10):2157-67. [PubMed:6448542 ]
  3. Rutkowski B, Slominska E, Szolkiewicz M, Smolenski RT, Striley C, Rutkowski P, Swierczynski J: N-methyl-2-pyridone-5-carboxamide: a novel uremic toxin? Kidney Int Suppl. 2003 May;(84):S19-21. [PubMed:12694300 ]
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Enzymes

Enzyme Details
1. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
1-Methylnicotinamide + Oxygen + Water → Nudifloramide + Hydrogen peroxide + Hydrogen Iondetails