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Showing NP-Card for Trimethylamine N-oxide (NP0000999)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:39 UTC
NP-MRD IDNP0000999
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrimethylamine N-oxide
DescriptionTrimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. In particular, trimethylamine-N-oxide is biosynthesized endogenously from trimethylamine, which is derived from choline, which can be derived from dietary lecithin (phosphatidylcholines) or dietary carnitine. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counteract the effects of increased concentrations of urea (due to kidney failure) and high levels can be used as a biomarker for kidney problems. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor. The concentration of TMAO in the blood increases after consuming foods containing carnitine or lecithin (phosphatidylcholines), if the bacteria that convert those substances to TMAO are present in the gut (PMID: 23614584 ). High concentrations of carnitine are found in red meat, some energy drinks, and certain dietary supplements; lecithin is found in eggs and is commonly used as an ingredient in processed food. High levels of TMAO are found in many seafoods. Some types of normal gut bacteria (e.G. Species of Acinetobacter) in the human gut convert dietary carnitine and dietary lecithin to TMAO (PMID: 21475195 ). TMAO alters cholesterol metabolism in the intestines, in the liver and in arterial wall. When TMAO is present, cholesterol metabolism is altered and there is an increased deposition of cholesterol within, and decreased removal of cholesterol from, peripheral cells such as those in the artery wall (PMID: 23563705 ). Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish. Trimethylamine N-oxide is found to be associated with maple syrup urine disease and propionic acidemia, which are inborn errors of metabolism. TMAO can also be found in Bacteroidetes, Ruminococcus (PMID: 26687352 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000999 (Trimethylamine N-oxide)


  Mrv1652305271900312D          

  5  4  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
M  CHG  2   2   1   5  -1
M  END
Download

3D MOL for NP0000999 (Trimethylamine N-oxide)

HMDB0000925
     RDKit          3D
Trimethylamine N-oxide
 14 13  0  0  0  0  0  0  0  0999 V2000
    1.1633   -0.7065   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.0033    0.4444 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.1901   -0.6487   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0032    1.3563   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632   -0.0767    1.7799 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9003   -1.4915   -0.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202   -1.1836    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381    0.0048   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -0.9070   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945   -1.5534    0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0569   -0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600    1.5617   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    2.0362    0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    1.5480   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
M  CHG  2   2   1   5  -1
M  END
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3D SDF for NP0000999 (Trimethylamine N-oxide)


  Mrv1652305271900312D          

  5  4  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
M  CHG  2   2   1   5  -1
M  END
> <DATABASE_ID>
NP0000999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3

> <INCHI_KEY>
UYPYRKYUKCHHIB-UHFFFAOYSA-N

> <FORMULA>
C3H9NO

> <MOLECULAR_WEIGHT>
75.1097

> <EXACT_MASS>
75.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
8.40468714229359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N,N-dimethylmethanamine oxide

> <ALOGPS_LOGP>
-2.01

> <JCHEM_LOGP>
-0.9342057176666667

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.662869181288156

> <JCHEM_POLAR_SURFACE_AREA>
23.06

> <JCHEM_REFRACTIVITY>
22.033

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethylamine-n-oxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0000999 (Trimethylamine N-oxide)

HMDB0000925
     RDKit          3D
Trimethylamine N-oxide
 14 13  0  0  0  0  0  0  0  0999 V2000
    1.1633   -0.7065   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.0033    0.4444 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.1901   -0.6487   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0032    1.3563   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632   -0.0767    1.7799 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9003   -1.4915   -0.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202   -1.1836    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381    0.0048   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -0.9070   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945   -1.5534    0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0569   -0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600    1.5617   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    2.0362    0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    1.5480   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
M  CHG  2   2   1   5  -1
M  END
Download

PDB for NP0000999 (Trimethylamine N-oxide)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for NP0000999 (Trimethylamine N-oxide)

COMPND    HMDB0000925
HETATM    1  C1  UNL     1       1.163  -0.707  -0.036  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.020   0.003   0.444  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.190  -0.649  -0.136  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.003   1.356  -0.041  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.063  -0.077   1.780  1.00  0.00           O1-
HETATM    6  H1  UNL     1       0.900  -1.491  -0.776  1.00  0.00           H  
HETATM    7  H2  UNL     1       1.720  -1.184   0.793  1.00  0.00           H  
HETATM    8  H3  UNL     1       1.838   0.005  -0.552  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.889  -0.907  -1.187  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.395  -1.553   0.435  1.00  0.00           H  
HETATM   11  H6  UNL     1      -2.057   0.057  -0.194  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.960   1.562  -0.531  1.00  0.00           H  
HETATM   13  H8  UNL     1      -0.168   2.036   0.809  1.00  0.00           H  
HETATM   14  H9  UNL     1      -0.797   1.548  -0.808  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    5
CONECT    3    9   10   11
CONECT    4   12   13   14
END
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SMILES for NP0000999 (Trimethylamine N-oxide)

C[N+](C)(C)[O-]
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INCHI for NP0000999 (Trimethylamine N-oxide)

InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
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View in JSmol
Synonyms
ValueSource
(CH3)3NOChEBI
Me3n(+)O(-)ChEBI
Me3n(O)ChEBI
N(CH3)3OChEBI
TMAOChEBI
Trimethylamine oxideChEBI
TrimethylaminoxidChEBI
TrimethyloxamineChEBI
N,N-Dimethylmethanamine N-oxideHMDB
TMA-oxideHMDB
Trimethylamine-N-oxideHMDB
TrioxHMDB
Trimethylammonium oxideHMDB
Chemical FormulaC3H9NO
Average Mass75.1097 Da
Monoisotopic Mass75.06841 Da
IUPAC NameN,N-dimethylmethanamine oxide
Traditional Nametrimethylamine-n-oxide
CAS Registry Number1184-78-7
SMILES
C[N+](C)(C)[O-]
InChI Identifier
InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
InChI KeyUYPYRKYUKCHHIB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trialkyl amine oxides. These are hydrocarbyl derivatives of the aminoxide anion, with the general formula R3N+[O-] or R3N=O, where R is an alkyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAminoxides
Direct ParentTrialkyl amine oxides
Alternative Parents
Substituents
  • Trialkyl amine oxide
  • Trisubstituted n-oxide
  • N-oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point95 - 99 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility454 mg/mLNot Available
LogP-2.570The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility57.8 g/LALOGPS
logP-2ALOGPS
logP-0.93ChemAxon
logS-0.11ALOGPS
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.03 m³·mol⁻¹ChemAxon
Polarizability8.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000925
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010413
KNApSAcK IDNot Available
Chemspider ID1113
KEGG Compound IDC01104
BioCyc IDTRIMENTHLAMINE-N-O
BiGG IDNot Available
Wikipedia LinkTrimethylamine_oxide
METLIN ID5876
PubChem Compound1145
PDB IDNot Available
ChEBI ID15724
Good Scents IDrw1293651
References
General References
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. [PubMed:8257730 ]
  3. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  4. Chung YL, Rider LG, Bell JD, Summers RM, Zemel LS, Rennebohm RM, Passo MH, Hicks J, Miller FW, Scott DL: Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies. Arthritis Rheum. 2005 Aug 15;53(4):565-70. [PubMed:16082628 ]
  5. Messana I, Forni F, Ferrari F, Rossi C, Giardina B, Zuppi C: Proton nuclear magnetic resonance spectral profiles of urine in type II diabetic patients. Clin Chem. 1998 Jul;44(7):1529-34. [PubMed:9665433 ]
  6. Maschke S, Wahl A, Azaroual N, Boulet O, Crunelle V, Imbenotte M, Foulard M, Vermeersch G, Lhermitte M: 1H-NMR analysis of trimethylamine in urine for the diagnosis of fish-odour syndrome. Clin Chim Acta. 1997 Jul 25;263(2):139-46. [PubMed:9246418 ]
  7. Kenyon S, Carmichael PL, Khalaque S, Panchal S, Waring R, Harris R, Smith RL, Mitchell SC: The passage of trimethylamine across rat and human skin. Food Chem Toxicol. 2004 Oct;42(10):1619-28. [PubMed:15304308 ]
  8. Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. [PubMed:9429235 ]
  9. On SL, Holmes B: Effect of inoculum size on the phenotypic characterization of Campylobacter species. J Clin Microbiol. 1991 May;29(5):923-6. [PubMed:2056060 ]
  10. Shepshelovich J, Goldstein-Magal L, Globerson A, Yen PM, Rotman-Pikielny P, Hirschberg K: Protein synthesis inhibitors and the chemical chaperone TMAO reverse endoplasmic reticulum perturbation induced by overexpression of the iodide transporter pendrin. J Cell Sci. 2005 Apr 15;118(Pt 8):1577-86. Epub 2005 Mar 22. [PubMed:15784681 ]
  11. Podadera P, Sipahi AM, Areas JA, Lanfer-Marquez UM: Diagnosis of suspected trimethylaminuria by NMR spectroscopy. Clin Chim Acta. 2005 Jan;351(1-2):149-54. [PubMed:15563884 ]
  12. Wolrath H, Stahlbom B, Hallen A, Forsum U: Trimethylamine and trimethylamine oxide levels in normal women and women with bacterial vaginosis reflect a local metabolism in vaginal secretion as compared to urine. APMIS. 2005 Jul-Aug;113(7-8):513-6. [PubMed:16086821 ]
  13. Watt K, Jess TJ, Kelly SM, Price NC, McEwan IJ: Induced alpha-helix structure in the aryl hydrocarbon receptor transactivation domain modulates protein-protein interactions. Biochemistry. 2005 Jan 18;44(2):734-43. [PubMed:15641800 ]
  14. Tang WH, Wang Z, Levison BS, Koeth RA, Britt EB, Fu X, Wu Y, Hazen SL: Intestinal microbial metabolism of phosphatidylcholine and cardiovascular risk. N Engl J Med. 2013 Apr 25;368(17):1575-84. doi: 10.1056/NEJMoa1109400. [PubMed:23614584 ]
  15. Wang Z, Klipfell E, Bennett BJ, Koeth R, Levison BS, Dugar B, Feldstein AE, Britt EB, Fu X, Chung YM, Wu Y, Schauer P, Smith JD, Allayee H, Tang WH, DiDonato JA, Lusis AJ, Hazen SL: Gut flora metabolism of phosphatidylcholine promotes cardiovascular disease. Nature. 2011 Apr 7;472(7341):57-63. doi: 10.1038/nature09922. [PubMed:21475195 ]
  16. Koeth RA, Wang Z, Levison BS, Buffa JA, Org E, Sheehy BT, Britt EB, Fu X, Wu Y, Li L, Smith JD, DiDonato JA, Chen J, Li H, Wu GD, Lewis JD, Warrier M, Brown JM, Krauss RM, Tang WH, Bushman FD, Lusis AJ, Hazen SL: Intestinal microbiota metabolism of L-carnitine, a nutrient in red meat, promotes atherosclerosis. Nat Med. 2013 May;19(5):576-85. doi: 10.1038/nm.3145. Epub 2013 Apr 7. [PubMed:23563705 ]
  17. Wang Z, Roberts AB, Buffa JA, Levison BS, Zhu W, Org E, Gu X, Huang Y, Zamanian-Daryoush M, Culley MK, DiDonato AJ, Fu X, Hazen JE, Krajcik D, DiDonato JA, Lusis AJ, Hazen SL: Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis. Cell. 2015 Dec 17;163(7):1585-95. doi: 10.1016/j.cell.2015.11.055. [PubMed:26687352 ]
  18. 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 ]