NP-MRD: Showing NP-Card for tetradecanimidic acid (NP0289250)

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Record Information

Version

2.0

Created at

2022-09-09 19:20:53 UTC

Updated at

2022-09-09 19:20:53 UTC

NP-MRD ID

NP0289250

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tetradecanimidic acid

Description

Myristamide, also known as N-tetradecanamide, belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, myristamide is considered to be a fatty amide lipid molecule. tetradecanimidic acid is found in Trypanosoma brucei. tetradecanimidic acid was first documented in 2007 (PMID: 17197513). Myristamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 28496060) (PMID: 30368294).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.7371   -0.9138   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640   -1.5989    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3820   -0.9854    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742   -1.1055   -0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -0.5234   -0.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243    0.9306   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369    1.4496   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177    0.7747   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3397    1.4520   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912    0.8656    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404    1.5950   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    1.1133    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291   -0.3391    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4459   -0.7990    1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8546   -2.1419    0.9696 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1109    0.0047    1.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7422   -0.9775    0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607    0.1681   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7273   -1.3925   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7128   -2.6796    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1211   -1.4562    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -1.6335    1.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853    0.0390    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5708   -0.6684   -1.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829   -2.1989   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -0.6847   -2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -1.0767   -0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8484    1.1863    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0633    1.4601   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.3595   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9580    2.5478   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -0.3178   -0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1949    0.9452    1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    1.3030   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060    2.5395   -0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.9051    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5860   -0.1958    0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644    2.6725    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691    1.4538   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424    1.2431    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8244    1.7250    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3444   -0.5178   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3511   -0.9557    0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1892   -2.9284    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8464   -2.3591    0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
M  END


  Mrv1533004161520572D          

 16 15  0  0  0  0            999 V2000
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289250

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H29NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H2,15,16)

> <INCHI_KEY>
QEALYLRSRQDCRA-UHFFFAOYSA-N

> <FORMULA>
C14H29NO

> <MOLECULAR_WEIGHT>
227.392

> <EXACT_MASS>
227.224914558

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.47699986925966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tetradecanamide

> <ALOGPS_LOGP>
5.92

> <JCHEM_LOGP>
4.560502833999999

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.883920541768287

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3815449951119882

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
69.70379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetradecanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.530   8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      31.198   8.772   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      29.864   6.462   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Myristic acid amide	ChEBI
Myristic amide	ChEBI
N-Tetradecanamide	ChEBI
Tetradecamide	ChEBI
Tetradecanamid	ChEBI
Tetradecanamide	ChEBI
Tetradecanoic acid amide	ChEBI
Tetradecylamide	ChEBI
Myristate amide	Generator
Tetradecanoate amide	Generator

Chemical Formula

C₁₄H₂₉NO

Average Mass

227.3920 Da

Monoisotopic Mass

227.22491 Da

IUPAC Name

tetradecanamide

Traditional Name

tetradecanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(N)=O

InChI Identifier

InChI=1S/C14H29NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H2,15,16)

InChI Key

QEALYLRSRQDCRA-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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (CPD6666-2 )

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	5.92	ALOGPS
logP	4.56	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	16.88	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	30.48 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

CPD6666-2

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69492

PDB ID

Not Available

ChEBI ID

137125

Good Scents ID

Not Available

References

General References

Nichols KK, Ham BM, Nichols JJ, Ziegler C, Green-Church KB: Identification of fatty acids and fatty acid amides in human meibomian gland secretions. Invest Ophthalmol Vis Sci. 2007 Jan;48(1):34-9. doi: 10.1167/iovs.06-0753. [PubMed:17197513 ]
Li H, Fan SF, Wang Y, Shen SG, Sun DX: Rapid Detection of Small Molecule Metabolites in Serum of Hepatocellular Carcinoma Patients Using Ultrafast Liquid Chromatography-Ion Trap-Time of Flight Tandem Mass Spectrometry. Anal Sci. 2017;33(5):573-578. doi: 10.2116/analsci.33.573. [PubMed:28496060 ]
Castillo-Peinado LS, Lopez-Bascon MA, Mena-Bravo A, Luque de Castro MD, Priego-Capote F: Determination of primary fatty acid amides in different biological fluids by LC-MS/MS in MRM mode with synthetic deuterated standards: Influence of biofluid matrix on sample preparation. Talanta. 2019 Feb 1;193:29-36. doi: 10.1016/j.talanta.2018.09.088. Epub 2018 Sep 25. [PubMed:30368294 ]
LOTUS database [Link]

Showing NP-Card for tetradecanimidic acid (NP0289250)

MOL for NP0289250 (tetradecanimidic acid)

3D MOL for NP0289250 (tetradecanimidic acid)

3D SDF for NP0289250 (tetradecanimidic acid)

3D-SDF for NP0289250 (tetradecanimidic acid)

PDB for NP0289250 (tetradecanimidic acid)

3D PDB for NP0289250 (tetradecanimidic acid)

SMILES for NP0289250 (tetradecanimidic acid)

INCHI for NP0289250 (tetradecanimidic acid)

Structure for NP0289250 (tetradecanimidic acid)

3D Structure for NP0289250 (tetradecanimidic acid)