NP-MRD: Showing NP-Card for Tiglylcarnitine (NP0086959)

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Record Information

Version

2.0

Created at

2022-05-11 16:35:46 UTC

Updated at

2022-05-11 16:35:46 UTC

NP-MRD ID

NP0086959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tiglylcarnitine

Description

Tiglylcarnitine 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, tiglylcarnitine is considered to be a fatty ester lipid molecule. Tiglylcarnitine was first documented in 2003 (PMID: 14518824). Tiglylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
    4.5381   -0.0357   -1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.4249   -1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4693    0.1761   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975   -0.5808    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.6899   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.3371   -1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3048    0.4835    0.7724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.9338    0.9265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1380    1.9982    1.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    3.1925    1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850    4.0916    0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    3.3450    2.3021 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0317   -0.1473    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1242   -1.0799    0.0253 N   0  0  2  0  0  4  0  0  0  0  0  0
   -0.9274   -1.8420   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4931   -0.4347   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330   -1.9870    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1239   -0.0343   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466    0.6703   -2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5552   -1.0341   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6715    0.9926   -2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.1524    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -0.9876    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439   -1.4186    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772    1.4707   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    1.6138    2.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    2.3050    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577   -0.7385    2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0501    0.3031    1.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1971   -1.7898    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -1.6065   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -2.9258   -0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0996    0.4485   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0977   -1.1865   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -0.2271   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -1.3970    0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -2.3954   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803   -2.7805    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  8 13  1  0
 14 13  1  1
 14 15  1  0
 14 16  1  0
 14 17  1  0
  2 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END


  Mrv1652305221920592D          

 18 17  0  0  0  0            999 V2000
    0.1105    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  0  0  0  0
M  CHG  2  13   1  15  -1
M  END
> <DATABASE_ID>
NP0086959

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3/b9-6+

> <INCHI_KEY>
WURBQCVBQNMUQT-RMKNXTFCSA-N

> <FORMULA>
C12H21NO4

> <MOLECULAR_WEIGHT>
243.2994

> <EXACT_MASS>
243.147058165

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.912485636954308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.89

> <JCHEM_LOGP>
-2.674568813471746

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.295140408588241

> <JCHEM_PKA_STRONGEST_BASIC>
-6.863909891770237

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
87.31509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiglylcarnitine

> <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       0.206   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.461   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.127  -1.540   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.207  -0.000   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       1.540   4.620   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   13                                                            
CONECT    6    1    9   18                                                  
CONECT    7   10   11                                                       
CONECT    8   10   13                                                       
CONECT    9    2    6   12                                                  
CONECT   10    7    8   17                                                  
CONECT   11    7   14   15                                                  
CONECT   12    9   16   17                                                  
CONECT   13    3    4    5    8                                             
CONECT   14   11                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   10   12                                                       
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylammonio)butanoate	ChEBI
3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylammonio)butanoic acid	Generator
Tiglyl-L-carnitine	HMDB

Chemical Formula

C₁₂H₂₁NO₄

Average Mass

243.2994 Da

Monoisotopic Mass

243.14706 Da

IUPAC Name

3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

tiglylcarnitine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H21NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3/b9-6+

InChI Key

WURBQCVBQNMUQT-RMKNXTFCSA-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
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
Branched fatty acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acylcarnitine (CHEBI:71179 )

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	-2.7	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-6.9	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	87.32 m³·mol⁻¹	ChemAxon
Polarizability	25.91 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

FDB022980

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833596

PDB ID

Not Available

ChEBI ID

71179

Good Scents ID

Not Available

References

General References

Fukao T, Zhang GX, Sakura N, Kubo T, Yamaga H, Hazama A, Kohno Y, Matsuo N, Kondo M, Yamaguchi S, Shigematsu Y, Kondo N: The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. J Inherit Metab Dis. 2003;26(5):423-31. [PubMed:14518824 ]

Showing NP-Card for Tiglylcarnitine (NP0086959)

MOL for NP0086959 (Tiglylcarnitine)

3D MOL for NP0086959 (Tiglylcarnitine)

3D SDF for NP0086959 (Tiglylcarnitine)

3D-SDF for NP0086959 (Tiglylcarnitine)

PDB for NP0086959 (Tiglylcarnitine)

3D PDB for NP0086959 (Tiglylcarnitine)

SMILES for NP0086959 (Tiglylcarnitine)

INCHI for NP0086959 (Tiglylcarnitine)

Structure for NP0086959 (Tiglylcarnitine)

3D Structure for NP0086959 (Tiglylcarnitine)