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Showing NP-Card for Cetyl myristoleate (NP0336874)

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Record Information
Version2.0
Created at2024-09-11 08:14:15 UTC
Updated at2024-09-11 08:14:15 UTC
NP-MRD IDNP0336874
Secondary Accession NumbersNone
Natural Product Identification
Common NameCetyl myristoleate
DescriptionCetyl myristoleate, also known as CMO, belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position. Cetyl myristoleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cetyl myristoleate is a chemical compound which is a type of fatty acid ester or, more specifically, a cetylated fatty acid (CFA). In follow-up studies in mice, a modest anti-inflammatory effect was observed. In animal studies, cetyl myristoleate was first reported to block inflammation and prevent adjuvant-induced arthritis at very high doses in rats. Outside of the human body, Cetyl myristoleate has been detected, but not quantified in, cereals and cereal products. This could make cetyl myristoleate a potential biomarker for the consumption of these foods. Cetyl myristoleate has been prepared by an esterification reaction between myristoleic acid and cetyl alcohol, catalyzed by p-toluenesulfonic acid monohydrate. Although cetyl myristoleate is sold as a dietary supplement, its possible benefits in the treatment of any medical condition are largely unknown and the Federal Trade Commission has taken legal action against supplement manufacturers for exaggerated claims. Other studies using identical and similar methods have failed to replicate this effect. There are some clinical trials appearing to show benefit for inflammation due to arthritis which should be taken into account. However, these low-quality clinical trials provide only limited scientific evidence of efficacy. It is the cetyl ester of myristoleic acid. There is some clinical evidence for the benefits of CFAs, which may contain cetyl myristoleate, in arthritic patients. One pilot study found that cetyl myristoleate may be beneficial against fibromyalgia.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336874 (Cetyl myristoleate)


  Mrv0541 05061310222D          

 32 31  0  0  0  0            999 V2000
  -10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9137    2.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1993    2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1993    3.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4848    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4848    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5191    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7703    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8046    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0559    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3757    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5178    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0546    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
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  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
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 12 10  2  0  0  0  0
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 16 15  1  0  0  0  0
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 20 18  1  0  0  0  0
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 22 20  1  0  0  0  0
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 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 30  2  0  0  0  0
 32 29  1  0  0  0  0
 32 30  1  0  0  0  0
M  END
Download

3D MOL for NP0336874 (Cetyl myristoleate)

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3D SDF for NP0336874 (Cetyl myristoleate)

  Mrv0541 05061310222D          

 32 31  0  0  0  0            999 V2000
  -10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9137    2.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1993    2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1993    3.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4848    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4848    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5191    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7703    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8046    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0559    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0901    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6612    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3414    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7690    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 30  2  0  0  0  0
 32 29  1  0  0  0  0
 32 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCC

> <INCHI_IDENTIFIER>
InChI=1S/C30H58O2/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-32-30(31)28-26-24-22-20-18-14-12-10-8-6-4-2/h10,12H,3-9,11,13-29H2,1-2H3/b12-10-

> <INCHI_KEY>
DYIOQMKBBPSAFY-BENRWUELSA-N

> <FORMULA>
C30H58O2

> <MOLECULAR_WEIGHT>
450.7803

> <EXACT_MASS>
450.4436811

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
62.50311519073939

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexadecyl (9Z)-tetradec-9-enoate

> <ALOGPS_LOGP>
10.52

> <JCHEM_LOGP>
11.810140841666666

> <ALOGPS_LOGS>
-7.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032727874424106

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
142.8529

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.07e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cetyl myristoleate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0336874 (Cetyl myristoleate)
Download
PDB for NP0336874 (Cetyl myristoleate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -18.837   9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.506   4.716   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.504  10.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.172   5.486   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -16.170   9.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.172   7.026   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.836  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.838   7.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.503   9.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.838   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.169  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.505  10.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.835   9.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.171   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.502  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.168   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.834  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.837  10.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.501   9.336   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.504   9.336   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.167  10.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.170  10.106   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.833   9.336   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.836   9.336   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.499  10.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.503  10.106   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.166   9.336   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.169   9.336   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.168  10.106   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.835  10.106   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.835  11.646   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.502   9.336   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   18                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   19                                                       
CONECT   18   14   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   32                                                       
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   29   30                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

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3D PDB for NP0336874 (Cetyl myristoleate)
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SMILES for NP0336874 (Cetyl myristoleate)
CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCC
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INCHI for NP0336874 (Cetyl myristoleate)
InChI=1S/C30H58O2/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-32-30(31)28-26-24-22-20-18-14-12-10-8-6-4-2/h10,12H,3-9,11,13-29H2,1-2H3/b12-10-
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View in JSmol
Synonyms
ValueSource
Cetyl myristoleic acidGenerator
CMOHMDB
Hexadecyl ester(Z)-9-tetradecenoic acidHMDB
Palmityl myristoleic acidGenerator
Cetyl myristoleateMeSH
cis-9-CetylmyristoleateMeSH
Chemical FormulaC30H58O2
Average Mass450.7803 Da
Monoisotopic Mass450.44368 Da
IUPAC Namehexadecyl (9Z)-tetradec-9-enoate
Traditional Namecetyl myristoleate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCC
InChI Identifier
InChI=1S/C30H58O2/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-32-30(31)28-26-24-22-20-18-14-12-10-8-6-4-2/h10,12H,3-9,11,13-29H2,1-2H3/b12-10-
InChI KeyDYIOQMKBBPSAFY-BENRWUELSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentWax monoesters  
Alternative Parents
Substituents
  • Wax monoester skeleton
    • 

  • Fatty alcohol ester
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.52ALOGPS
logP11.81ChemAxon
logS-7.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity142.85 m³·mol⁻¹ChemAxon
Polarizability62.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038307  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017636  
KNApSAcK IDNot Available
Chemspider ID4947787  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCetyl myristoleate  
METLIN IDNot Available
PubChem Compound6443825  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References