NP-MRD: Showing NP-Card for Propionylcarnitine (NP0333358)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2024-06-04 16:45:10 UTC

Updated at

2024-06-06 00:11:32 UTC

NP-MRD ID

NP0333358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Propionylcarnitine

Description

Levocarnitine propionate hydrochloride 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. Levocarnitine propionate hydrochloride is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309172007262D          

 15 14  0  0  0  0            999 V2000
   -0.6445   -0.1993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0695   -0.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977   -0.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    0.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445    0.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586    1.0357    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.0768    0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586    1.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2117    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3503   -0.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3503   -1.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644   -1.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  6  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0333358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H](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/p+1/t8-/m1/s1

> <INCHI_KEY>
UFAHZIUFPNSHSL-MRVPVSSYSA-O

> <FORMULA>
C10H20NO4

> <MOLECULAR_WEIGHT>
218.272

> <EXACT_MASS>
218.138684548

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
23.082876437979156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-carboxy-2-(propanoyloxy)propyl]trimethylazanium

> <ALOGPS_LOGP>
-1.92

> <JCHEM_LOGP>
-3.7458447908050787

> <ALOGPS_LOGS>
-2.99

> <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>
63.6

> <JCHEM_REFRACTIVITY>
66.42660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propionyl-L-carnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.203  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.130  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.463  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.796  -1.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.129  -0.372   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.463   1.167   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.203   1.167   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.536   1.933   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      -3.877   1.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.536   3.473   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.129   2.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.521  -1.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.521  -2.701   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.188  -3.473   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.854  -3.473   0.000  0.00  0.00           O+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14   15                                                  
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
Levocarnitine propionic acid hydrochloride	Generator
(3R)-3-(Propionyloxy)-4-(trimethylammonio)butanoate	ChEBI
(R)-3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt	ChEBI
O-Propanoyl-(R)-carnitine	ChEBI
O-Propanoylcarnitine	ChEBI
O-Propinoyl-L-carnitine	ChEBI
(3R)-3-(Propionyloxy)-4-(trimethylammonio)butanoic acid	Generator
O-Propanoyl-carnitine	ChEBI
(-)-Propionylcarnitine	HMDB
C3-Carnitine	HMDB
L-Carnitine propionyl ester	HMDB
L-Propionylcarnitine	HMDB
Levocarnitine propil	HMDB
O-Propanoyl-L-carnitine	HMDB
O-Propionyl-L-carnitine	HMDB
Propanoyl-L-carnitine	HMDB
Propionyl-L-carnitine	HMDB
Propionylcarnitine	HMDB
Acylcarnitine C3:0	HMDB
C3:0 Carnitine	HMDB

Chemical Formula

C₁₀H₂₀NO₄

Average Mass

218.2720 Da

Monoisotopic Mass

218.13868 Da

IUPAC Name

[(2R)-3-carboxy-2-(propanoyloxy)propyl]trimethylazanium

Traditional Name

propionyl-L-carnitine

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H](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/p+1/t8-/m1/s1

InChI Key

UFAHZIUFPNSHSL-MRVPVSSYSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, D₂O, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-04	View Spectrum

Species

Species of Origin

Not Available

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 derivative
Carboxylic acid
Organic nitrogen compound
Amine
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-1.9	ALOGPS
logP	-3.7	ChemAxon
logS	-3	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	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	66.43 m³·mol⁻¹	ChemAxon
Polarizability	23.08 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

138875

KEGG Compound ID

C03017

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157837

PDB ID

Not Available

ChEBI ID

53210

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Propionylcarnitine (NP0333358)

MOL for NP0333358 (Propionylcarnitine)

3D MOL for NP0333358 (Propionylcarnitine)

3D SDF for NP0333358 (Propionylcarnitine)

3D-SDF for NP0333358 (Propionylcarnitine)

PDB for NP0333358 (Propionylcarnitine)

3D PDB for NP0333358 (Propionylcarnitine)

SMILES for NP0333358 (Propionylcarnitine)

INCHI for NP0333358 (Propionylcarnitine)

Structure for NP0333358 (Propionylcarnitine)

3D Structure for NP0333358 (Propionylcarnitine)