NP-MRD: Showing NP-Card for Heptanoylcarnitine (NP0339230)

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Record Information

Version

2.0

Created at

2024-09-11 20:34:17 UTC

Updated at

2024-09-11 20:34:17 UTC

NP-MRD ID

NP0339230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heptanoylcarnitine

Description

Heptanoylcarnitine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Heptanoylcarnitine was first documented in 2020 (PMID: 32101032). Based on a literature review a small amount of articles have been published on Heptanoylcarnitine (PMID: 39182606) (PMID: 38438006) (PMID: 36510714).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262323062D          

 19 18  0  0  0  0            999 V2000
   13.2875   -4.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7000   -3.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5250   -3.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9375   -4.1505    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.7000   -4.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9375   -2.7215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4625   -4.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0499   -3.4360    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.7644   -3.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3354   -3.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6374   -2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0499   -6.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4625   -5.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2875   -5.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7000   -6.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2249   -6.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8124   -7.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9874   -7.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5749   -7.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  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
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
  5 14  1  0  0  0  0
 15 14  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
NP0339230

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1/C14H27NO4/c1-5-6-7-8-9-14(18)19-12(10-13(16)17)11-15(2,3)4/h12H,5-11H2,1-4H3

> <INCHI_KEY>
VDPCTFWULDLKHT-UHFFFAOYNA-N

> <FORMULA>
C14H27NO4

> <MOLECULAR_WEIGHT>
273.373

> <EXACT_MASS>
273.194008353

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.22623667694976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.96757013080508

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186891978034

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
95.6677

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
O-heptanoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      24.803  -7.748   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.573  -6.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.113  -6.414   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.883  -7.748   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      25.573  -9.081   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.883  -5.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      23.263  -7.748   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      22.493  -6.414   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      23.827  -5.644   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.159  -7.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.723  -5.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.493 -11.749   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.263 -10.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.803 -10.415   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      25.573 -11.749   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.953 -11.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.183 -13.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.643 -13.082   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.873 -14.416   0.000  0.00  0.00           C+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3                                                            
CONECT    5    1   14                                                       
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₇NO₄

Average Mass

273.3730 Da

Monoisotopic Mass

273.19401 Da

IUPAC Name

3-(heptanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

O-heptanoylcarnitine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1/C14H27NO4/c1-5-6-7-8-9-14(18)19-12(10-13(16)17)11-15(2,3)4/h12H,5-11H2,1-4H3

InChI Key

VDPCTFWULDLKHT-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	ChemAxon
pKa (Strongest Acidic)	4.22	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	11	ChemAxon
Refractivity	95.67 m³·mol⁻¹	ChemAxon
Polarizability	31.23 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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

74303

Good Scents ID

Not Available

References

General References

Sobhi HF, Mercer KE, Lan RS, Yeruva L, Ten Have GAM, Deutz NEP, Piccolo BD, Debedat J, Pack LM, Adams SH: Novel odd-chain cyclopropane fatty acids: detection in a mammalian lipidome and uptake by hepatosplanchnic tissues. J Lipid Res. 2024 Aug 27;65(10):100632. doi: 10.1016/j.jlr.2024.100632. [PubMed:39182606 ]
Hu T, Zhang W, Han F, Zhao R, Liu H, An Z: Machine learning reveals serum myristic acid, palmitic acid and heptanoylcarnitine as biomarkers of coronary artery disease risk in patients with type 2 diabetes mellitus. Clin Chim Acta. 2024 Mar 15;556:117852. doi: 10.1016/j.cca.2024.117852. Epub 2024 Mar 2. [PubMed:38438006 ]
Liu XD, Meng XJ, Zhang XM, Li J, Pan XF: [A non-targeted metabolomics study on serum of occupational people exposed with nanometer titanium dioxide particles (TiO(2)-NPs)]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2022 Nov 20;40(11):813-820. doi: 10.3760/cma.j.cn121094-20210318-00158. [PubMed:36510714 ]
Sobhi HF, Zhao X, Plomgaard P, Hoene M, Hansen JS, Karus B, Niess AM, Haring HU, Lehmann R, Adams SH, Xu G, Weigert C: Identification and regulation of the xenometabolite derivatives cis- and trans-3,4-methylene-heptanoylcarnitine in plasma and skeletal muscle of exercising humans. Am J Physiol Endocrinol Metab. 2020 May 1;318(5):E701-E709. doi: 10.1152/ajpendo.00510.2019. Epub 2020 Feb 26. [PubMed:32101032 ]

Showing NP-Card for Heptanoylcarnitine (NP0339230)

MOL for NP0339230 (Heptanoylcarnitine)

3D MOL for NP0339230 (Heptanoylcarnitine)

3D SDF for NP0339230 (Heptanoylcarnitine)

3D-SDF for NP0339230 (Heptanoylcarnitine)

PDB for NP0339230 (Heptanoylcarnitine)

3D PDB for NP0339230 (Heptanoylcarnitine)

SMILES for NP0339230 (Heptanoylcarnitine)

INCHI for NP0339230 (Heptanoylcarnitine)

Structure for NP0339230 (Heptanoylcarnitine)

3D Structure for NP0339230 (Heptanoylcarnitine)