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Showing NP-Card for butyrobetaine (NP0285037)

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Record Information
Version2.0
Created at2022-09-09 13:01:14 UTC
Updated at2022-09-09 13:01:14 UTC
NP-MRD IDNP0285037
Secondary Accession NumbersNone
Natural Product Identification
Common Namebutyrobetaine
Description4-Trimethylammoniobutanoic acid, also known as 4-butyrobetaine or deoxycarnitine, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. 4-Trimethylammoniobutanoic acid is a weakly acidic compound (based on its pKa). 4-Trimethylammoniobutanoic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 4-Trimethylammoniobutanoic acid has been detected, but not quantified in, several different foods, such as ryes, triticales, tartary buckwheats, wild rices, and corns. This could make 4-trimethylammoniobutanoic acid a potential biomarker for the consumption of these foods. butyrobetaine is found in Ailuropoda melanoleuca, Homo sapiens and Trypanosoma brucei. butyrobetaine was first documented in 1979 (PMID: 398096). An amino-acid betaine gamma-aminobutyric acid zwitterion in which all of the hydrogens attached to the nitrogen are replaced by methyl groups (PMID: 12729644) (PMID: 3311009) (PMID: 6773946) (PMID: 10491993) (PMID: 2007906) (PMID: 3148329).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0285037 (butyrobetaine)


  Mrv1652307191923392D          

 10  9  0  0  0  0            999 V2000
    9.7697   -6.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4819   -5.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6273   -6.1581    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    9.0574   -5.7547    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.7697   -6.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1985   -6.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9108   -5.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0350   -5.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3482   -6.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2197   -6.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  1  0  0  0  0
  9  3  1  0  0  0  0
 10  3  1  0  0  0  0
  7  6  1  0  0  0  0
M  CHG  2   3   1   4  -1
M  END
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3D MOL for NP0285037 (butyrobetaine)

     RDKit          3D

 25 24  0  0  0  0  0  0  0  0999 V2000
   -0.9982    1.4686    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    0.1061   -0.0887 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.7675    0.0470   -1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884   -0.4021    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967   -0.7510    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040    0.0119    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3987   -0.8982    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141   -0.0359    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821   -0.5189    0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    1.3532    0.1706 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.0573    1.6333    1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530    2.0778   -0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0396    1.8831   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192   -0.2867   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694    1.0770   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -0.5670   -2.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668   -0.2428    1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553    0.2753    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217   -1.4610    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229   -1.3854    0.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -1.4812   -0.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    0.6216   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746    0.6222    1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849   -1.5573   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406   -1.5894    1.0478 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
M  CHG  2   2   1  10  -1
M  END
Download

3D SDF for NP0285037 (butyrobetaine)


  Mrv1652307191923392D          

 10  9  0  0  0  0            999 V2000
    9.7697   -6.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4819   -5.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6273   -6.1581    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    9.0574   -5.7547    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.7697   -6.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1985   -6.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9108   -5.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0350   -5.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3482   -6.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2197   -6.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  1  0  0  0  0
  9  3  1  0  0  0  0
 10  3  1  0  0  0  0
  7  6  1  0  0  0  0
M  CHG  2   3   1   4  -1
M  END
> <DATABASE_ID>
NP0285037

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3

> <INCHI_KEY>
JHPNVNIEXXLNTR-UHFFFAOYSA-N

> <FORMULA>
C7H15NO2

> <MOLECULAR_WEIGHT>
145.1995

> <EXACT_MASS>
145.110278729

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.19807438182574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-3.15

> <JCHEM_LOGP>
-3.968509901138413

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.457564906027561

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
62.277800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyrobetaine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0285037 (butyrobetaine)

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PDB for NP0285037 (butyrobetaine)
HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0      18.237 -11.511   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.566 -10.734   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      23.571 -11.495   0.000  0.00  0.00           N+1
HETATM    4  O   UNK     0      16.907 -10.742   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      18.237 -13.049   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.904 -11.503   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.233 -10.726   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.332 -10.149   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.917 -12.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.810 -12.833   0.000  0.00  0.00           C+0
CONECT    1    2    4    5                                                  
CONECT    2    1    6                                                       
CONECT    3    7    8    9   10                                             
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    3    6                                                       
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    3                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0285037 (butyrobetaine)
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SMILES for NP0285037 (butyrobetaine)
C[N+](C)(C)CCCC([O-])=O
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INCHI for NP0285037 (butyrobetaine)
InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3
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View in JSmol
Synonyms
ValueSource
3-DehydroxycarnitineChEBI
4-(N-Trimethylamino)butyrateChEBI
4-(Trimethylamino)butanoateChEBI
4-ButyrobetaineChEBI
ActinineChEBI
ButyrobetaineChEBI
DeoxycarnitineChEBI
gamma-ButyrobetainChEBI
gamma-ButyrobetaineChEBI
4-(N-Trimethylamino)butyric acidGenerator
4-(Trimethylamino)butanoic acidGenerator
g-ButyrobetainGenerator
Γ-butyrobetainGenerator
g-ButyrobetaineGenerator
Γ-butyrobetaineGenerator
4-TrimethylammoniobutanoateGenerator
Deoxy-carnitineHMDB
4-TrimethylaminobutyrateHMDB
4-N-Trimethylammonium butyrateHMDB
4-Trimethylammoniobutanoic acidHMDB
Chemical FormulaC7H15NO2
Average Mass145.1995 Da
Monoisotopic Mass145.11028 Da
IUPAC Name4-(trimethylazaniumyl)butanoate
Traditional Namebutyrobetaine
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)CCCC([O-])=O
InChI Identifier
InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3
InChI KeyJHPNVNIEXXLNTR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ailuropoda melanoleucaLOTUS Database
Homo sapiensLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentStraight chain fatty acids  
Alternative Parents
Substituents
  • Straight chain fatty acid
    • 

  • Quaternary ammonium salt
    • 

  • Tetraalkylammonium salt
    • 

  • Carboxylic acid salt
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP-3.2ALOGPS
logP-4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.28 m³·mol⁻¹ChemAxon
Polarizability16.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001161  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB024107  
KNApSAcK IDNot Available
Chemspider ID705  
KEGG Compound IDC01181  
BioCyc IDGAMMA-BUTYROBETAINE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound725  
PDB IDNot Available
ChEBI ID16244  
Good Scents IDNot Available
References
General References
  1. Hewawasam P, Ding M, Chen N, King D, Knipe J, Pajor L, Ortiz A, Gribkoff VK, Starrett J: Synthesis of water-soluble prodrugs of BMS-191011: a maxi-K channel opener targeted for post-stroke neuroprotection. Bioorg Med Chem Lett. 2003 May 19;13(10):1695-8. doi:  10.1016/s0960-894x(03)00296-8. [PubMed:12729644  ] 
  2. Siliprandi N, Ciman M, Sartorelli L: Myocardial carnitine transport. Basic Res Cardiol. 1987;82 Suppl 1:53-62. doi: 10.1007/978-3-662-08390-1_7. [PubMed:3311009  ] 
  3. Rebouche CJ, Engel AG: Significance of renal gamma-butyrobetaine hydroxylase for carnitine biosynthesis in man. J Biol Chem. 1980 Sep 25;255(18):8700-5. [PubMed:6773946  ] 
  4. Terada N, Inoue F, Okochi M, Nakajima H, Kizaki Z, Kinugasa A, Sawada T: Measurement of carnitine precursors, epsilon-trimethyllysine and gamma-butyrobetaine in human serum by tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):89-95. doi:  10.1016/s0378-4347(99)00112-7. [PubMed:10491993  ] 
  5. Rebouche CJ, Chenard CA: Metabolic fate of dietary carnitine in human adults: identification and quantification of urinary and fecal metabolites. J Nutr. 1991 Apr;121(4):539-46. doi: 10.1093/jn/121.4.539. [PubMed:2007906  ] 
  6. Nobile S, Deshusses J: Evidence for a role of a vicinal dithiol in the transport of gamma-butyrobetaine in Agrobacterium sp. Biochimie. 1988 Oct;70(10):1411-6. doi: 10.1016/0300-9084(88)90013-2. [PubMed:3148329  ] 
  7. Seim H, Kleber HP, Strack E: [Reduction of L-carnitine to gamma-butyrobetaine by Escherichia coli]. Z Allg Mikrobiol. 1979;19(10):753-8. doi: 10.1002/jobm.3630191011. [PubMed:398096  ] 
  8. LOTUS database [Link]