NP-MRD: Showing NP-Card for n-butyryl-l-carnitin (NP0207321)

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Record Information

Version

2.0

Created at

2022-09-05 03:53:12 UTC

Updated at

2022-09-05 03:53:12 UTC

NP-MRD ID

NP0207321

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-butyryl-l-carnitin

Description

Butyrylcarnitine 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. n-butyryl-l-carnitin is found in Ailuropoda melanoleuca and Trypanosoma brucei. Butyrylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    3.5132    1.4782    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289    0.4483    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575   -0.9311    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778   -0.8833    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702   -0.9790    1.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -0.7386   -0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -0.7044    0.0359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7702   -1.9420   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066   -3.0928   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -3.3977    1.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8384   -3.8257   -0.6684 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.8627    0.5902   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2549    0.7657   -0.2374 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8246    0.2141    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0379    0.4978   -1.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4599    2.2335   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6200    2.4868    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390    1.2421   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0367    1.4010   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6637    0.7410    2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183    0.4372    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -1.6627    1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7430   -1.1834   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664   -0.8146    1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4368   -1.8935   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.1424   -0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004    0.7702   -1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685    1.3584    0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1975   -0.8197    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0681    0.2783    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059    0.8264    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891    0.7978   -1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -0.5115   -1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7055    1.2507   -2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150    2.4818   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507    2.7807   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1719    2.4424    0.9678 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
 12 13  1  0
 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  1
  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


  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>
NP0207321

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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

Chemical Formula

C₁₁H₂₁NO₄

Average Mass

231.2887 Da

Monoisotopic Mass

231.14706 Da

IUPAC Name

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

Traditional Name

L-carnitine butyryl ester

CAS Registry Number

Not Available

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

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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ailuropoda melanoleuca	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

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 )

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	24.78 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-butyryl-l-carnitin (NP0207321)

MOL for NP0207321 (n-butyryl-l-carnitin)

3D MOL for NP0207321 (n-butyryl-l-carnitin)

3D SDF for NP0207321 (n-butyryl-l-carnitin)

3D-SDF for NP0207321 (n-butyryl-l-carnitin)

PDB for NP0207321 (n-butyryl-l-carnitin)

3D PDB for NP0207321 (n-butyryl-l-carnitin)

SMILES for NP0207321 (n-butyryl-l-carnitin)

INCHI for NP0207321 (n-butyryl-l-carnitin)

Structure for NP0207321 (n-butyryl-l-carnitin)

3D Structure for NP0207321 (n-butyryl-l-carnitin)