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Bovine Rumen Metabolome Database



Showing metabocard for Nicotinic acid (RMDB01488)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:49
Accession Number RMDB01488
Common Name Nicotinic acid
Description Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient.
Synonyms
  1. 3-Carboxylpyridine
  2. 3-Carboxypyridine
  3. 3-Pyridinecarboxylate
  4. 3-Pyridinecarboxylic acid
  5. 3-Pyridylcarboxylate
  6. 3-Pyridylcarboxylic acid
  7. Akotin
  8. Apelagrin
  9. Daskil
  10. Efacin
  11. Enduracin
  12. Linic
  13. Niac
  14. Niacor
  15. Nicacid
  16. Nicangin
  17. Nico-Span
  18. Nicodelmine
  19. Niconacid
  20. Nicosan 3
  21. Nicotinate
  22. Nicotinic acid
  23. Nicotinipca
  24. Nicyl
  25. Nyclin
  26. Pellagrin
  27. Pelonin
  28. Slo-niacin
  29. niacin
  30. niacine
  31. nicamin
  32. nicobid
  33. nicocap
  34. nicolar
  35. wampocap
Chemical IUPAC Name pyridine-3-carboxylic acid
Chemical Formula C6H5NO2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; aromatic compound; heterocyclic compound
Biofunction
  • Essential vitamins
Application
Source
  • Exogenous
Average Molecular Weight 123.109
Monoisotopic Molecular Weight 123.032028
Isomeric SMILES OC(=O)C1=CN=CC=C1
Canonical SMILES OC(=O)C1=CN=CC=C1
KEGG Compound ID C00253 Link Image
BioCyc ID NIACINE Link Image
BiGG ID 34401 Link Image
Wikipedia Link Nicotinic acid Link Image
METLIN ID 6272 Link Image
PubChem Compound 938 Link Image
PubChem Substance 11537626 Link Image
ChEBI ID 15940 Link Image
CAS Registry Number 59-67-6
InChI Identifier InChI=1/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
Synthesis Reference McElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.
Melting Point (Experimental) 236.6 oC
Experimental Water Solubility 18.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 83.100006 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 0.36 [SANGSTER (1993)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.29 [Predicted by ALOGPS]; 0.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1D0V Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 37.45 +/- 7.48 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 58.6 +/- 13.2 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 43 +/- 11 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 62 +/- 17 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 41 +/- 12 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Diacylglycerol O-acyltransferase 2
Enzyme 1 [top]
Enzyme 1 ID 535
Enzyme 1 Name Diacylglycerol O-acyltransferase 2
Enzyme 1 Synonyms
  1. Diglyceride acyltransferase 2
Enzyme 1 Gene Name DGAT2
Enzyme 1 Protein Sequence >Diacylglycerol O-acyltransferase 2
MKTLIAAYSGVLRGTGSSILSALQDLFSVTWLNRAKVEKQLQVISVLQWVLSFLVLGVAC
SVILMYTFCTDCWLIAVLYFTWLVFDWNTPKKGGRRSQWVRNWAVWRYFRDYFPIQLVKT
HNLLTSRNYIFGYHPHGIMGLGAFCNFSTEATEVSKKFPGIRPYLATLAGNFRMPVLREY
LMSGGICPVNRDTIDYLLSKNGSGNAIIIVVGGAAESLSSMPGKNAVTLRNRKGFVKLAL
RHGADLVPTYSFGENEVYKQVIFEEGSWGRWVQKKFQKYIGFAPCIFHGRGLFSSDTWGL
VPYSKPITTVVGEPITIPRLERPTQQDIDLYHAMYVQALVKLFDQHKTKFGLPETEVLEV
N
Enzyme 1 Number of Residues 361
Enzyme 1 Molecular Weight 40895.3
Enzyme 1 Theoretical pI 9.81
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Involved in diacylglycerol O-acyltransferase activity
Enzyme 1 Specific Function Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation
Enzyme 1 Pathways
  • Glycerolipid metabolism
  • triacylglycerol biosynthesis
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • 43-63 65-85
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 42454647 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q70VZ8 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name DGAT2_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1086 bp
ATGAAGACCCTCATAGCCGCCTACTCCGGGGTCCTGCGAGGCACTGGCTCCAGCATCCTC
TCTGCCCTCCAGGACCTGTTTTCTGTCACTTGGCTCAATAGGGCCAAGGTAGAGAAGCAG
CTCCAAGTCATCTCGGTGCTACAATGGGTCCTGTCTTTCCTCGTGCTGGGAGTGGCCTGC
AGCGTCATCCTCATGTACACATTCTGCACCGATTGCTGGCTCATTGCCGTGCTCTACTTC
ACCTGGCTGGTGTTTGACTGGAACACACCCAAGAAAGGTGGCAGGAGGTCACAGTGGGTC
CGAAACTGGGCTGTGTGGCGCTACTTTCGAGACTACTTTCCCATTCAGCTGGTGAAGACA
CACAACTTACTGACCAGCAGGAACTACATCTTTGGGTACCATCCCCATGGCATCATGGGC
CTGGGTGCCTTCTGCAACTTCAGCACAGAGGCCACAGAAGTAAGCAAGAAGTTCCCTGGC
ATAAGGCCCTACCTGGCCACGCTGGCCGGCAACTTCCGGATGCCAGTGCTGCGGGAGTAC
CTGATGTCTGGAGGCATCTGCCCAGTGAACCGGGACACCATAGACTACTTGCTTTCAAAG
AATGGGAGTGGCAATGCCATCATCATCGTGGTGGGGGGCGCGGCTGAATCCCTGAGCTCC
ATGCCCGGCAAGAATGCAGTCACCCTGCGCAATCGCAAGGGCTTTGTGAAACTGGCCCTG
CGCCATGGAGCCGACCTGGTTCCCACCTACTCCTTTGGGGAGAATGAGGTGTACAAGCAG
GTGATCTTTGAGGAGGGCTCCTGGGGCCGGTGGGTGCAGAAGAAGTTCCAGAAGTACATT
GGCTTTGCCCCATGCATCTTCCATGGTCGAGGCCTCTTCTCCTCTGACACCTGGGGGCTG
GTGCCCTACTCCAAGCCCATCACCACTGTCGTGGGCGAGCCCATTACCATCCCCAGGCTG
GAGCGCCCGACGCAGCAGGACATCGACCTGTACCACGCCATGTACGTGCAAGCCCTGGTG
AAGCTCTTCGACCAGCATAAGACCAAGTTCGGCCTCCCGGAGACCGAGGTCCTGGAGGTG
AACTGA
Enzyme 1 GenBank Gene ID AJ519787 Link Image
Enzyme 1 GeneCard ID DGAT2 Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 11q13.5
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available