NP-MRD: Showing NP-Card for (+-)-propionylcarnitine (NP0243390)

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Record Information

Version

2.0

Created at

2022-09-07 03:55:43 UTC

Updated at

2022-09-07 03:55:43 UTC

NP-MRD ID

NP0243390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+-)-propionylcarnitine

Description

Propionylcarnitine 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, propionylcarnitine is considered to be a fatty ester lipid molecule. Propionylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, propionylcarnitine participates in a number of enzymatic reactions. In particular, propionylcarnitine can be biosynthesized from propionyl-CoA and L-carnitine through its interaction with the enzyme carnitine O-acetyltransferase. In addition, propionylcarnitine can be biosynthesized from propionyl-CoA and L-carnitine; which is catalyzed by the enzyme carnitine O-acetyltransferase. In humans, propionylcarnitine is involved in oxidation of branched-chain fatty acids. Outside of the human body, Propionylcarnitine is found, on average, in the highest concentration within milk (cow). Propionylcarnitine has also been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, and cow milks. This could make propionylcarnitine a potential biomarker for the consumption of these foods. Propionylcarnitine is a potentially toxic compound. (+-)-propionylcarnitine is found in Ailuropoda melanoleuca and Trypanosoma brucei. (+-)-propionylcarnitine was first documented in 1984 (PMID: 6723070). Propionylcarnitine, with regard to humans, has been found to be associated with several diseases such as prosthesis/missing teeth, periodontal probing depth, crohn's disease, and tooth decay; propionylcarnitine has also been linked to the inborn metabolic disorder celiac disease (PMID: 14586648) (PMID: 3126357).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
    4.1417   -1.4047   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -1.2160    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0457   -0.2011    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1953    0.3739   -0.9559 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    0.1424    0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137    1.0932    0.4603 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0031    2.3297    1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0014    3.2964    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2019    3.3468    1.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    4.2459   -0.0638 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4020    0.5875    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -0.5411   -0.4414 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8668   -0.5988   -1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700   -0.5713   -0.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4065   -1.7447    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191   -0.6055   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -1.3067   -1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740   -2.4135   -0.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4351   -0.8776    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4686   -2.1786    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077    1.4625   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954    2.0631    2.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986    2.8088    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7949    0.4229    1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0347    1.4158   -0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0282   -1.3294   -1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -1.0545   -2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    0.3749   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5155    0.4354   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1669   -0.9601   -1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -1.2825   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -1.8012    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -2.6166   -0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387   -1.6952    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  6
  7 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  0
 13 27  1  0
 13 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
M  CHG  2  10  -1  12   1
M  END

Propionylglycine.mol
  Mrv0541 02231218462D          

 15 14  0  0  0  0            999 V2000
   -0.4125   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -1.0164    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.7309    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
  1  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  2  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  3 13  1  0  0  0  0
M  CHG  2   4   1  15  -1
M  END
> <DATABASE_ID>
NP0243390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3

> <INCHI_KEY>
UFAHZIUFPNSHSL-UHFFFAOYSA-N

> <FORMULA>
C10H19NO4

> <MOLECULAR_WEIGHT>
217.2622

> <EXACT_MASS>
217.131408101

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.721274988631023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.27

> <JCHEM_LOGP>
-3.7458447908050787

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.185139998188834

> <JCHEM_PKA_STRONGEST_BASIC>
-7.054133284063387

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
77.26370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propionyl-L-carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Propionylglycine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.770  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540  -0.564   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -2.310  -1.897   0.000  0.00  0.00           N+1
HETATM    5  O   UNK     0      -0.770   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.770   3.437   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.310  -0.357   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310  -3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.850  -1.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310  -1.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.850  -1.897   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.540  -3.231   0.000  0.00  0.00           O-1
CONECT    1    2    4                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2   13                                                       
CONECT    4    1   10   11   12                                             
CONECT    5    6    2                                                       
CONECT    6    7    5    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13   14   15    3                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt	ChEBI
O-Propionylcarnitine	ChEBI
Propionyl carnitine	ChEBI
(+/-)-propionylcarnitine chloride	HMDB
(3-Carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt	HMDB
L-Propionylcarnitine	HMDB
O-Propanoylcarnitine	HMDB
Propionyl-carnitine	HMDB
Propionyl-L-carnitine	HMDB
Propionylcarnitine, (+-)-isomer	HMDB
Propionylcarnitine, (R)-isomer	HMDB

Chemical Formula

C₁₀H₁₉NO₄

Average Mass

217.2622 Da

Monoisotopic Mass

217.13141 Da

IUPAC Name

3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

propionyl-L-carnitine

CAS Registry Number

Not Available

SMILES

CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3

InChI Key

UFAHZIUFPNSHSL-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

O-acylcarnitine (CHEBI:28867 )
Fatty acyl carnitines (C03017 )

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	-2.3	ALOGPS
logP	-3.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.19	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	7	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	22.72 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

HMDB0000824

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022268

KNApSAcK ID

Not Available

Chemspider ID

96904

KEGG Compound ID

C03017

BioCyc ID

Not Available

BiGG ID

1862604

Wikipedia Link

Not Available

METLIN ID

5787

PubChem Compound

107738

PDB ID

Not Available

ChEBI ID

28867

Good Scents ID

Not Available

References

General References

Leonard JV, Vijayaraghavan S, Walter JH: The impact of screening for propionic and methylmalonic acidaemia. Eur J Pediatr. 2003 Dec;162 Suppl 1:S21-4. doi: 10.1007/s00431-003-1345-1. Epub 2003 Oct 30. [PubMed:14586648 ]
Penn D, Schmidt-Sommerfeld E, Jakobs C, Bieber LL: Amniotic fluid propionylcarnitine in methylmalonic aciduria. J Inherit Metab Dis. 1987;10(4):376-82. doi: 10.1007/BF01799980. [PubMed:3126357 ]
Di Donato S, Rimoldi M, Garavaglia B, Uziel G: Propionylcarnitine excretion in propionic and methylmalonic acidurias: a cause of carnitine deficiency. Clin Chim Acta. 1984 May 16;139(1):13-21. doi: 10.1016/0009-8981(84)90187-6. [PubMed:6723070 ]
LOTUS database [Link]

Showing NP-Card for (+-)-propionylcarnitine (NP0243390)

MOL for NP0243390 ((+-)-propionylcarnitine)

3D MOL for NP0243390 ((+-)-propionylcarnitine)

3D SDF for NP0243390 ((+-)-propionylcarnitine)

3D-SDF for NP0243390 ((+-)-propionylcarnitine)

PDB for NP0243390 ((+-)-propionylcarnitine)

3D PDB for NP0243390 ((+-)-propionylcarnitine)

SMILES for NP0243390 ((+-)-propionylcarnitine)

INCHI for NP0243390 ((+-)-propionylcarnitine)

Structure for NP0243390 ((+-)-propionylcarnitine)

3D Structure for NP0243390 ((+-)-propionylcarnitine)