MiMeDB: Showing metabocard for Butyrylcarnitine (MMDBc0033539)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:46 UTC

Update Date

2024-04-30 20:12:11 UTC

Metabolite ID

MMDBc0033539

Metabolite Identification

Common Name

Butyrylcarnitine

Description

Butyrylcarnitine, also known as (3R)-3-(butyryloxy)-4-(trimethylammonio)butanoate or L-carnitine butyryl ester, is classified as a member of the acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Butyrylcarnitine is considered to be practically insoluble (in water) and acidic. Butyrylcarnitine is elevated in patients with short-chain acyl-CoA dehydrogenase (SCAD) deficiency, in infants with acute acidosis and generalized muscle weakness, and in middle-aged patients with chronic myopathy localized in muscle (OMIM: 201470 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920562D          

 16 15  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0954    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9520    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
M  CHG  2  12   1  14  -1
M  END
> <DATABASE_ID>
MMDBc0033539

> <DATABASE_NAME>
MIME

> <SMILES>
CCCC(=O)OC(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

> <INCHI_KEY>
QWYFHHGCZUCMBN-UHFFFAOYSA-N

> <FORMULA>
C11H21NO4

> <MOLECULAR_WEIGHT>
231.2887

> <EXACT_MASS>
231.147058165

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
24.776806153977763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
81.86469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-carnitine butyryl ester

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.645  -1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.311   3.644   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.645   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       7.645  -0.206   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0       7.645   5.954   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.978   3.644   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    1    6                                                       
CONECT    6    5   11                                                       
CONECT    7    9   10                                                       
CONECT    8    9   12                                                       
CONECT    9    7    8   16                                                  
CONECT   10    7   13   14                                                  
CONECT   11    6   15   16                                                  
CONECT   12    2    3    4    8                                             
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

Synonyms

Value	Source
O-Butyrylcarnitine	ChEBI
(3-Carboxy-2-hydroxypropyl)trimethyl-L-butyrate	HMDB
(R)-3-Carboxy-N,N,N-trimethyl-2-(1-oxobutoxy)-1-propanaminium	HMDB
Butyryl-L-carnitine	HMDB
Ester with (3-carboxy-2-hydroxypropyl)trimethylammonium L-butyric acid	HMDB
Ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium butyric acid	HMDB
L-Carnitine butyryl ester	HMDB
N-Butyryl-L(-)-carnitine	HMDB
O-Butanoylcarnitine	HMDB
Butylcarnitine	MeSH

Molecular Formula

C₁₁H₂₁NO₄

Average Mass

231.2887

Monoisotopic Mass

231.147058165

IUPAC Name

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

Traditional Name

L-carnitine butyryl ester

CAS Registry Number

25576-40-3

SMILES

CCCC(=O)OC(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

InChI Key

QWYFHHGCZUCMBN-UHFFFAOYSA-N

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

butyrate ester (CHEBI:7676 )
C4-acylcarnitine (CHEBI:7676 )
Fatty acyl carnitines (C02862 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
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	24.78 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

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Fibroblasts
Placenta
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease	Decreased	Association	Human Blood	HMDB	16425363
Obesity	Decreased	Association	Human Urine	HMDB	26910390
Short chain acyl-coa dehydrogenase deficiency		Association	Human Urine	HMDB	7776094
Very long chain acyl-coa dehydrogenase deficiency	Decreased	Association	Human Blood	HMDB	9034211
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Obesity	Slight Decrease	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.152	0.011			uM	Adult (>18 years old)	Both	Celiac disease	HMDB	16425363
Human Blood	Detected and Quantified	0.38				uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	HMDB	24453145
Human Urine	Detected and Quantified	565.44	32.46			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	HMDB	26910390
Human Blood	Detected and Quantified	0.2169	0.0736			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified			0	8.966	umol/mmol creatinine	Infant (0-1 year old)	Both	Short chain acyl-CoA dehydrogenase deficiency (SCAD)	HMDB	7776094
Human Blood	Detected and Quantified	0.005		0.0	0.009	uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	HMDB	9034211
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	7776094
Human Blood	Detected and Quantified	<0.12				uM	Adolescent (13-18 years old)	Male	Normal	HMDB	24453145
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.024	0.007			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	22546835
Human Urine	Detected and Quantified			0.05	0.33	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.079		0.023	0.174	uM	Children (1-13 years old)	Both	Normal	HMDB	9034211
Human Urine	Detected and Quantified	0.11	0.06			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.13		0.11	0.16	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Urine	Detected and Quantified	0.13	0.07			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Feces	Detected and Quantified	0.15	0.06			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.21	0.09			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Feces	Detected and Quantified	0.21	0.1			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.26	0.16			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.26	0.1			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	0.267	0.013			uM	Adult (>18 years old)	Both	Normal	HMDB	16425363
Human Blood	Detected and Quantified	0.39		0.31	0.55	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Urine	Detected and Quantified	0.76		0.12	1.81	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	702.56	39.76			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	26910390
Human Urine	Detected and Quantified	1.368	1.1114			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	0.069	0.047			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	0.078	0.035			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Urine	Detected and Quantified	2.3594	1.3471			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Saliva	Detected and Quantified	0.073	0.044			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.10	0.45	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.10	0.45	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022795

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02862

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439829

PDB ID

Not Available

ChEBI ID

7676

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1016/s0022-3476(95)70207-5. [PubMed:7776094 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
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. doi: 10.1016/j.cccn.2003.07.006. [PubMed:14568186 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Butyrylcarnitine (MMDBc0033539)

MOL for #<Metabolite:0x00007f9238632f00>

3D MOL for #<Metabolite:0x00007f9238632f00>

3D SDF for #<Metabolite:0x00007f9238632f00>

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Structure for #<Metabolite:0x00007f9238632f00>

3D Structure for #<Metabolite:0x00007f9238632f00>