NP-MRD: Showing NP-Card for Butyryl-L-carnitine (NP0083485)

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Record Information

Version

2.0

Created at

2022-04-29 04:31:06 UTC

Updated at

2022-04-29 04:31:06 UTC

NP-MRD ID

NP0083485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butyryl-L-carnitine

Description

Butyrylcarnitine, also known as O-butanoylcarnitine, belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, butyrylcarnitine is considered to be a fatty ester lipid molecule. Butyrylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyrylcarnitine exists in all eukaryotes, ranging from yeast to humans. Butyrylcarnitine is a potentially toxic compound. Butyrylcarnitine, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, obesity, and attachment loss; butyrylcarnitine has also been linked to several inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency and celiac disease. Butyryl-L-carnitine is found in Homo sapiens (Urine). Butyryl-L-carnitine was first documented in 1983 (PMID: 6618689). An optically active form of Butyrylcarnitine having L-configuration (PMID: 14568186) (PMID: 7776094).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    3.4798    1.1528    0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.9549   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600    0.1567   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    0.8100   -1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0832    1.7338   -1.9960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    0.3990   -0.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918    0.8917   -0.1024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9196    1.4540    1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010    2.5887    1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    3.0494    0.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    3.2302    2.7645 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8414   -0.0387   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -1.3366   -0.1173 N   0  0  1  0  0  4  0  0  0  0  0  0
   -2.2690   -1.5968    1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601   -1.9952   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -2.1869   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    2.2147    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4288    0.8618    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467    0.4840    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.3999   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518    1.9123   -1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -0.8465   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743    0.0667   -2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8206    1.7525   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    0.7181    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9297    1.8937    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8248    0.4824   -0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -0.1111   -1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203   -1.5457    1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.0821    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -2.6892    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825   -2.7531   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993   -2.4240   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857   -1.1867   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0863   -1.8719    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672   -2.3503   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -3.1924   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  7 12  1  0
 13 12  1  1
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END

      
  Mrv1652304251823492D          

 16 15  0  0  0  0            999 V2000
10018.531810018.7422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10018.531810019.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.246410020.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.959910019.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.673410020.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.391110019.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.246410020.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.254710018.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.254710017.5185    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10018.153110016.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.965910017.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.110310016.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.817710018.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.103510018.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.389410018.3290    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10017.103510019.5673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  8  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  CHG  2   9   1  15  -1
M  END
> <DATABASE_ID>
NP0083485

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1

> <INCHI_KEY>
QWYFHHGCZUCMBN-SECBINFHSA-N

> <FORMULA>
C11H21NO4

> <MOLECULAR_WEIGHT>
231.292

> <EXACT_MASS>
231.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
24.796522551548037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-3.3012761258050785

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.26892391250365

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057078620656008

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
81.8647

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-butanoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-18         0                                  
HETATM    1  C   UNK     0    8701.2598701.652   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8701.2598703.531   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8702.5938704.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8703.9258703.531   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8705.2578704.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8706.5978703.531   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8702.5938705.837   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8702.6098700.907   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8702.6098699.368   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0    8700.5528698.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8703.9368698.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8702.3398697.852   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8699.9268700.881   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8698.5938701.652   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8697.2608700.881   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0    8698.5938703.192   0.000  0.00  0.00           O+0
CONECT    1    2    8   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoate	ChEBI
Butyryl-L-carnitine	ChEBI
L-Carnitine butyryl ester	ChEBI
N-Butyryl-L-(-)-carnitin	ChEBI
O-Butanoyl-(R)-carnitine	ChEBI
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoic acid	Generator
Butylcarnitine	HMDB
O-Butanoyl-carnitine	HMDB
O-Butanoylcarnitine	HMDB
Butyrylcarnitine	ChEBI

Chemical Formula

C₁₁H₂₁NO₄

Average Mass

231.2920 Da

Monoisotopic Mass

231.14706 Da

IUPAC Name

(3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

O-butanoylcarnitine

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1

InChI Key

QWYFHHGCZUCMBN-SECBINFHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens (Urine)	Animalia	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-butanoylcarnitine (CHEBI:21949 )
Fatty acyl carnitines (LMFA07070003 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.1	ALOGPS
logP	-3.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	81.86 m³·mol⁻¹	ChemAxon
Polarizability	24.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002013

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022795

KNApSAcK ID

Not Available

Chemspider ID

184820

KEGG Compound ID

C02862

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6436

PubChem Compound

213144

PDB ID

Not Available

ChEBI ID

21949

Good Scents ID

Not Available

References

General References

Young SP, Matern D, Gregersen N, Stevens RD, Bali D, Liu HM, Koeberl DD, Millington DS: A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 2003 Nov;337(1-2):103-13. [PubMed:14568186 ]
Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]
Golan R, Soffer Y, Katz S, Weissenberg R, Wasserzug O, Lewin LM: Carnitine and short-chain acylcarnitines in the lumen of the human male reproductive tract. Int J Androl. 1983 Aug;6(4):349-57. doi: 10.1111/j.1365-2605.1983.tb00549.x. [PubMed:6618689 ]

Showing NP-Card for Butyryl-L-carnitine (NP0083485)

MOL for NP0083485 (Butyryl-L-carnitine)

3D MOL for NP0083485 (Butyryl-L-carnitine)

3D SDF for NP0083485 (Butyryl-L-carnitine)

3D-SDF for NP0083485 (Butyryl-L-carnitine)

PDB for NP0083485 (Butyryl-L-carnitine)

3D PDB for NP0083485 (Butyryl-L-carnitine)

SMILES for NP0083485 (Butyryl-L-carnitine)

INCHI for NP0083485 (Butyryl-L-carnitine)

Structure for NP0083485 (Butyryl-L-carnitine)

3D Structure for NP0083485 (Butyryl-L-carnitine)