NP-MRD: Showing NP-Card for trans-Hexadec-2-enoyl carnitine (NP0087489)

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Record Information

Version

2.0

Created at

2022-05-11 16:51:05 UTC

Updated at

2022-05-11 16:51:05 UTC

NP-MRD ID

NP0087489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-Hexadec-2-enoyl carnitine

Description

Trans-Hexadec-2-enoyl carnitine, also known as (2E)-hexadecenoyl-carnitine, 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, trans-hexadec-2-enoyl carnitine is considered to be a fatty ester lipid molecule. An O-hexadecenoylcarnitine having (2E)-hexadecenoyl as the acyl substituent. Trans-Hexadec-2-enoyl carnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Trans-Hexadec-2-enoyl carnitine, with regard to humans, has been linked to the inborn metabolic disorder very long chain acyl-coa dehydrogenase deficiency.

Structure

MOL 3D MOL SDF PDB SMILES InChI

Untitled Document-5
  Mrv1652303132023272D          

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    3.2151    1.8563    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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    4.6441    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730    0.2062    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.7875   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6605   -0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 12  1  0  0  0  0
M  CHG  2   2  -1   8   1
M  END

     RDKit          3D

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   -8.4281   -2.0562   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3116   -1.5160   -1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 21 23  1  0
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 25 24  1  1
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 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
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  5 38  1  0
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  6 40  1  0
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  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
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 13 54  1  0
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 19 58  1  1
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 28 69  1  0
 28 70  1  0
 28 71  1  0
M  CHG  2  23  -1  25   1
M  END

Untitled Document-5
  Mrv1652303132023272D          

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    6.0730    0.2062    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
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    3.9296   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
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 26 27  1  0  0  0  0
 12 28  2  0  0  0  0
  1 12  1  0  0  0  0
M  CHG  2   2  -1   8   1
M  END
> <DATABASE_ID>
NP0087489

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h17-18,21H,5-16,19-20H2,1-4H3/b18-17+

> <INCHI_KEY>
SOYNLLDADLOGAM-ISLYRVAYSA-N

> <FORMULA>
C23H43NO4

> <MOLECULAR_WEIGHT>
397.5918

> <EXACT_MASS>
397.319208869

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.16788998383875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2E)-hexadec-2-enoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
2.2647046771949206

> <ALOGPS_LOGS>
-7.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.171784931901458

> <JCHEM_PKA_STRONGEST_BASIC>
-6.812938595726752

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
138.17000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.49e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E)-hexadec-2-enoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-5                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-MAR-20         0                                  
HETATM    1  O   UNK     0       8.669  -1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.002   3.465   0.000  0.00  0.00           O-1
HETATM    3  C   UNK     0       7.335   2.695   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.669   3.465   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.335   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.669   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.003   1.155   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      11.336   0.385   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      12.670  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.566  -0.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.106   1.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.335  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.002  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.668  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.334  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.667  -1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.667  -1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.001  -1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.334  -1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.668  -1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.002  -1.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.335  -1.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.669  -1.925   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.003  -1.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.336  -1.925   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.670  -1.155   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.335  -3.465   0.000  0.00  0.00           O+0
CONECT    1    6   12                                                       
CONECT    2    3                                                            
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   28    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   12                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
trans-2-Hexadecenoyl-carnitine	ChEBI
(2E)-Hexadecenoyl-carnitine	HMDB

Chemical Formula

C₂₃H₄₃NO₄

Average Mass

397.5918 Da

Monoisotopic Mass

397.31921 Da

IUPAC Name

3-[(2E)-hexadec-2-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(2E)-hexadec-2-enoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h17-18,21H,5-16,19-20H2,1-4H3/b18-17+

InChI Key

SOYNLLDADLOGAM-ISLYRVAYSA-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
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
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-hexadecenoylcarnitine (CHEBI:86031 )

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	1.44	ALOGPS
logP	2.26	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-6.8	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	19	ChemAxon
Refractivity	138.17 m³·mol⁻¹	ChemAxon
Polarizability	49.17 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

HMDB0006317

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023884

KNApSAcK ID

Not Available

Chemspider ID

26948132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2734943

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477817

PDB ID

Not Available

ChEBI ID

86031

Good Scents ID

Not Available

References

General References

Showing NP-Card for trans-Hexadec-2-enoyl carnitine (NP0087489)

MOL for NP0087489 (trans-Hexadec-2-enoyl carnitine)

3D MOL for NP0087489 (trans-Hexadec-2-enoyl carnitine)

3D SDF for NP0087489 (trans-Hexadec-2-enoyl carnitine)

3D-SDF for NP0087489 (trans-Hexadec-2-enoyl carnitine)

PDB for NP0087489 (trans-Hexadec-2-enoyl carnitine)

3D PDB for NP0087489 (trans-Hexadec-2-enoyl carnitine)

SMILES for NP0087489 (trans-Hexadec-2-enoyl carnitine)

INCHI for NP0087489 (trans-Hexadec-2-enoyl carnitine)

Structure for NP0087489 (trans-Hexadec-2-enoyl carnitine)

3D Structure for NP0087489 (trans-Hexadec-2-enoyl carnitine)