Nicotinamide (BioCAD00000015180)

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Metabolite Card

Formula: C6H6N2O (122.048)
SMILES: NC(=O)C1=CC=CN=C1

Synonyms [en]

nicotinamide; niacinamide; Nicotinic acid amide; vitamin PP; pyridine-3-carboxamide; beta-Pyridinecarboxamide

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Nicotinamide. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000015180). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Niacinamide, also known as nicotinamide (NAM), is a form of vitamin B3 found in food and used as a dietary supplement and medication. Niacinamide 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. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. The structure of nicotinamide consists of a pyridine ring to which a primary amide group is attached in the meta position. It is an amide of nicotinic acid. As an aromatic compound, it undergoes electrophilic substitution reactions and transformations of its two functional groups. Niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate by the enzyme nicotinamide phosphoribosyltransferase. In humans, niacinamide is involved in the metabolic disorder called the nad+ signalling pathway (cancer). Niacinamide is an odorless tasting compound. Outside of the human body, niacinamide is found, on average, in the highest concentration within a few different foods, such as common sages, cow milk, and cocoa beans and in a lower concentration in common pea. Niacinamide has also been detected, but not quantified in several different foods, such as yardlong beans, roselles, apples, oyster mushrooms, and swiss chards. Niacinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables. It is commonly added to cereals and other foods. Many multivitamins contain 20–30 mg of vitamin B3 and it is also available in higher doses. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake.

Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 11032-50-1
  • CAS Registry Number: 1122-39-0
  • CAS Registry Number: 20579-43-5
  • CAS Registry Number: 55740-80-2
  • CAS Registry Number: 6304-18-3
  • CAS Registry Number: 63748-44-7
  • CAS Registry Number: 688035-62-3
  • CAS Registry Number: 98-92-0
  • CAS Registry Number: 99548-31-9
  • PubChem: 3453
  • PubChem: 936
  • ChEBI: ChEBI:17154
  • HMDB: HMDB0001406
  • HMDB: HMDB01406
  • KEGG: C00153
  • KEGG: C00153 D00036
  • BioCyc: NIACINAMIDE
  • NCBI MeSH: Niacinamide
  • Wikipedia: Nicotinamide
  • DrugBank: DB02701
  • RefMet: RM0156450
  • MoNA: BAF_UVA_POS001203
  • MoNA: BAF_UVA_POS001204
  • MoNA: Bruker_HCD_library001827
  • MoNA: CCMSLIB00000479720
  • MoNA: CCMSLIB00000577900
  • MoNA: CCMSLIB00005464061
  • MoNA: CCMSLIB00005720342
  • MoNA: EMBL-MCF_spec96250
  • MoNA: EMBL_MCF_2_0_HRMS_Library000106
  • MoNA: FiehnHILIC000609
  • MoNA: FiehnHILIC002177
  • MoNA: FiehnLib000412
  • MoNA: GLS00132
  • MoNA: HMDB0001406_c_ms_1161
  • MoNA: HMDB0001406_c_ms_1185
  • MoNA: HMDB0001406_ms_ms_1559
  • MoNA: HMDB0001406_ms_ms_1560
  • MoNA: HMDB0001406_ms_ms_1561
  • MoNA: JP005706
  • MoNA: JP010812
  • MoNA: KO003582
  • MoNA: KO003583
  • MoNA: KO003584
  • MoNA: KO003585
  • MoNA: KO003586
  • MoNA: KZ000064
  • MoNA: LU025101
  • MoNA: LU025102
  • MoNA: LU025103
  • MoNA: LU025104
  • MoNA: LU025105
  • MoNA: LU025106
  • MoNA: ML005101
  • MoNA: MoNA002238
  • MoNA: MoNA002239
  • MoNA: MoNA002240
  • MoNA: MoNA010191
  • MoNA: MoNA010192
  • MoNA: MoNA010193
  • MoNA: MoNA010194
  • MoNA: MoNA010195
  • MoNA: MoNA011207
  • MoNA: MoNA011208
  • MoNA: MoNA011209
  • MoNA: MoNA011210
  • MoNA: MoNA016769
  • MoNA: MoNA024294
  • MoNA: MoNA032517
  • MoNA: MoNA032519
  • MoNA: MoNA032520
  • MoNA: MoNA035773
  • MoNA: MoNA035774
  • MoNA: MoNA035776
  • MoNA: MoNA037333
  • MoNA: MoNA038082
  • MoNA: MoNA038676
  • MoNA: OUF00389
  • MoNA: PR010181
  • MoNA: PR100181
  • MoNA: PR100182
  • MoNA: PR100401
  • MoNA: PR100402
  • MoNA: PS030801
  • MoNA: PS030802
  • MoNA: PS030803
  • MoNA: PS030804
  • MoNA: PS100901
  • MoNA: PS100902
  • MoNA: PS100903
  • MoNA: PS100904
  • MoNA: PS100905
  • MoNA: PT103080
  • MoNA: PT103083
  • MoNA: PT110090
  • MoNA: PT110093
  • MoNA: RP022301
  • MoNA: RP022302
  • MoNA: RP022303
  • MoNA: VF-NPL-QEHF027664
  • MoNA: VF-NPL-QEHF027665
  • MoNA: VF-NPL-QEHF027666
  • MoNA: VF-NPL-QEHF027667
  • MoNA: VF-NPL-QEHF027668
  • MoNA: VF-NPL-QEHF027669
  • MoNA: VF-NPL-QEHF027670
  • MoNA: VF-NPL-QEHF027671
  • MoNA: VF-NPL-QEHF027672
  • MoNA: VF-NPL-QEHF027673
  • MoNA: VF-NPL-QEHF027674
  • MoNA: VF-NPL-QEHF027675
  • MoNA: VF-NPL-QEHF027676
  • MoNA: VF-NPL-QEHF027677
  • MoNA: VF-NPL-QEHF027678
  • MoNA: WA002672
  • MoNA: WA002673
  • MoNA: WA002674
  • MoNA: WA002675
  • Metlin: METLIN_1497
  • Coconut NaturalProduct: CNP0071253.0
  • Coconut NaturalProduct: CNP0150794.0
  • Coconut NaturalProduct: CNP0157310.0
  • Coconut NaturalProduct: CNP0297347.0
  • Coconut NaturalProduct: CNP0355268.0
  • Coconut NaturalProduct: CNP0375292.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00102 3.2.2.5 NAD+ glycohydrolase
KEGG:R00119 2.4.99.20 NADP+:nicotinate ADP-ribosyltransferase
KEGG:R00555 2.4.2.31 NAD+:protein-L-arginine ADP-D-ribosyltransferase
KEGG:R01268 3.5.1.19 nicotinamide amidohydrolase
KEGG:R01269 2.1.1.1 S-adenosyl-L-methionine:nicotinamide N-methyltransferase
KEGG:R01270 3.2.2.14 nicotinamide D-ribonucleotide phosphoribohydrolase
KEGG:R01271 2.4.2.12 nicotinamide-D-ribonucleotide:diphosphate phospho-alpha-D-ribosyltransferase
KEGG:R01273 3.2.2.3 N-ribosylnicotinamide ribohydrolase
KEGG:R02294 2.4.2.1 N-ribosylnicotinamide:orthophosphate ribosyltransferase
KEGG:R03447 2.4.2.37 NAD+:[dinitrogen reductase](ADP-D-ribosyl)transferase
KEGG:R04074 2.4.2.36 NAD+:peptide-diphthamide N-(ADP-D-ribosyl)transferase
KEGG:R04176 2.4.2.30 NAD+:poly(adenosine diphosphate D-ribose)ADP-D-ribosyltransferase
KEGG:R10629 3.2.2.6 NAD+ nicotinamide-lyase (cyclic-ADP-ribose-forming)
KEGG:R10631 2.4.99.20 NADP+ nicotinamide-lyase (2'-phospho-cyclic-ADP-ribose-forming)
KEGG:R10633 2.3.1.286 C00003 + C01997 + C00001<=>C00153 + C02415 + C20658 + C00080
KEGG:R10634 2.3.1.286 C00003 + C20743 + C00001<=>C00153 + C02188 + C20658 + C00080
KEGG:R10685 2.4.2.60 NAD+:glycine ADP-D-ribosyltransferase (dehydroalanine-producing)
KEGG:R12026 2.4.2.59 NAD+:glycine ADP-D-ribosyltransferase (sulfide-adding)
KEGG:R13186 2.3.1.313 [lipoyl-carrier protein]-N6-[(R)-lipoyl]-L-lysine:NAD+ lipoyltranferase (NAD+-hydrolysing; 2''-O-lipoyl-ADP-D-ribose-forming)
BioCyc:RXN0-7078 2.3.1.286 CPD3O-0 + NAD + WATER --> Protein-L-lysine + CPD-14762 + NIACINAMIDE
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Organism Source

Taxonomy Source

  1. Aframomum amaniense [ncbi taxid: ]
  2. Alectoria divergens [ncbi taxid: ]
  3. Anemarrhena asphodeloides [ncbi taxid: 59045]
  4. Arabidopsis thaliana [ncbi taxid: 3702]
  5. Aristolochia zollingeriana [ncbi taxid: 171878]
  6. Armillaria mellea [ncbi taxid: 47429]
  7. Austrotaxus spicata [ncbi taxid: 89478]
  8. Balanophora involucrata [ncbi taxid: 2894844]
  9. Bartramia pomiformis [ncbi taxid: 52976]
  10. Beilschmiedia anacardioides [ncbi taxid: ]
  11. Bos taurus [ncbi taxid: 9913]
  12. Calotropis procera [ncbi taxid: 141467]
  13. Cedrus libani [ncbi taxid: 93692]
  14. Cephalaria grossheimii [ncbi taxid: ]
  15. Cerinthe minor [ncbi taxid: 131385]
  16. Cistanche deserticola [ncbi taxid: 161395]
  17. Cistanche tubulosa [ncbi taxid: 161397]
  18. Citrullus lanatus [ncbi taxid: 3654]
  19. Citrus wilsonii [ncbi taxid: 475932]
  20. Coccus ilicis [ncbi taxid: ]
  21. Craspidospermum verticillatum [ncbi taxid: 184384]
  22. Crocus sativus [ncbi taxid: 82528]
  23. Dictyopteris acrostichoides [ncbi taxid: 157155]
  24. Dioscorea japonica [ncbi taxid: 4673]
  25. Ehretia dicksonii [ncbi taxid: 1398146]
  26. Escherichia coli [ncbi taxid: 562]
  27. FOOD SAKE [ncbi taxid: ]
  28. Homo sapiens [ncbi taxid: 9606]
  29. Humulus japonicus [ncbi taxid: 3485]
  30. Hydrangea macrophylla [ncbi taxid: 23110]
  31. Hypericum ascyron [ncbi taxid: 210378]
  32. Isaria felina [ncbi taxid: ]
  33. Ixeris stolonifera [ncbi taxid: 268077]
  34. Justicia paniculata [ncbi taxid: ]
  35. Khaya ivorensis [ncbi taxid: 486173]
  36. Khaya senegalensis [ncbi taxid: 587579]
  37. Larix cajanderi [ncbi taxid: 501393]
  38. Lotus japonicus [ncbi taxid: 34305]
  39. Lupinus verbasciformis [ncbi taxid: ]
  40. Lycium barbarum [ncbi taxid: 112863]
  41. Melaleuca rhaphiophylla [ncbi taxid: ]
  42. Mus musculus [ncbi taxid: 10090]
  43. Nama hispidum [ncbi taxid: ]
  44. Ophiocordyceps sinensis [ncbi taxid: 72228]
  45. Penicillium paxilli [ncbi taxid: 70109]
  46. Phallus impudicus [ncbi taxid: 146781]
  47. Pieris napi [ncbi taxid: 78633]
  48. Pinellia pedatisecta [ncbi taxid: 199222]
  49. Pinellia ternata [ncbi taxid: 199225]
  50. Pisum sativum [ncbi taxid: ]
  51. Saccharomyces cerevisiae [ncbi taxid: 4932]
  52. Salvia officinalis [ncbi taxid: 38868]
  53. Senecio renardii [ncbi taxid: ]
  54. Senna siamea [ncbi taxid: 346999]
  55. Sextonia rubra [ncbi taxid: 128702]
  56. Stigma croci [ncbi taxid: ]
  57. Streptomyces paulus [ncbi taxid: 285551]
  58. Taraxacum formosanum [ncbi taxid: 170733]
  59. Theobroma cacao [ncbi taxid: 3641]
  60. Triaenophora rupestris [ncbi taxid: 441503]
  61. Virola multinervia [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_NAD-BIOSYNTHESIS-III NAD salvage
BioCyc:META_PWY-6689 tRNA splicing I
BioCyc:META_PWY-3502 superpathway of NAD biosynthesis in eukaryotes
BioCyc:META_PWY3O-4107 NAD salvage pathway V (PNC V cycle)
BioCyc:YEAST_PWY3O-4107 NAD salvage pathway
BioCyc:ARA_PWY-5381 pyridine nucleotide cycling (plants)
BioCyc:LEISH_PWY-5381 pyridine nucleotide cycling (plants)
BioCyc:ECOO157_PYRIDNUCSAL-PWY NAD salvage pathway I
BioCyc:SYNEL_PYRIDNUCSAL-PWY NAD salvage pathway I
BioCyc:ECOL413997_PYRIDNUCSAL-PWY NAD salvage pathway I
BioCyc:10403S_RAST_PYRIDNUCSAL-PWY NAD salvage pathway I
BioCyc:GCF_000013425_PYRIDNUCSAL-PWY NAD salvage pathway I
BioCyc:META_NAD-BIOSYNTHESIS-III NAD biosynthesis III (from nicotinamide)
BioCyc:META_PWY-5381 pyridine nucleotide cycling (plants)
BioCyc:META_PYRIDNUCSAL-PWY NAD salvage pathway I (PNC VI cycle)
BioCyc:ARA_PWY-6909 thiazole biosynthesis III (eukaryotes)
BioCyc:MTBH37RV_PYRIDNUCSAL-PWY NAD salvage pathway I (PNC VI cycle)
BioCyc:MTBCDC1551_PYRIDNUCSAL-PWY NAD salvage pathway I
BioCyc:SCO_P345-PWY aldoxime degradation
BioCyc:PCHR_PWY-3502 superpathway of NAD biosynthesis in eukaryotes
View All Pathways