NP-MRD: Showing NP-Card for Monomyristin (NP0137523)

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Record Information

Version

2.0

Created at

2022-05-30 16:55:00 UTC

Updated at

2022-05-30 16:55:00 UTC

NP-MRD ID

NP0137523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monomyristin

Description

1-Monomyristoylglycerol, also known as 1-tetradecanoylglycerol or monomyristin, belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position. Monomyristin is found in Caenorhabditis elegans and Serenoa repens. 1-Monomyristoylglycerol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 54  0  0  0  0  0  0  0  0999 V2000
    8.0609    1.5846    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414    1.0226   -0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1416    0.7275   -0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9556   -0.2639    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4680   -0.6383    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181   -1.2356   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522   -1.7686   -0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639   -0.9451   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1410   -0.3769    0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112    0.4143    0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4453   -0.1755    0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9120   -0.9155   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040   -1.3014   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.1235   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8550    1.0382   -0.2848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6075   -0.3023    0.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5222    0.7754    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8793    0.1714    0.5192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2165   -0.6904   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9376    1.2311    0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0557    1.9574   -0.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9088    2.3088    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250    0.7865    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1987    2.1095    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1605    0.0540   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8687    1.7624   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143    1.6629   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062    0.3394   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2707    0.2354    1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5088   -1.1937    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9341    0.3566    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3855   -1.2811    1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6018   -2.0536   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804   -0.4718   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.2460   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5380   -2.7273   -0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812   -0.0678   -1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4753   -1.5111   -0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528    0.3093    1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453   -1.1939    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682    1.2809    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    0.9815    1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6245   -0.8570    1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2109    0.6382    1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573   -1.9726   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7311   -0.3509   -1.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -2.0052   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -1.9176    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5942    1.3415   -0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1886    1.4344    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7589   -0.4661    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3506   -0.1233   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6437    1.8935    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8855    0.7025    0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0095    2.0564   -0.6604 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  1
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
M  END


  Mrv1533004241515402D          

 21 20  0  0  0  0            999 V2000
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC(=O)OCC(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C17H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)21-15-16(19)14-18/h16,18-19H,2-15H2,1H3

> <INCHI_KEY>
DCBSHORRWZKAKO-UHFFFAOYSA-N

> <FORMULA>
C17H34O4

> <MOLECULAR_WEIGHT>
302.455

> <EXACT_MASS>
302.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.08603155988344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxypropyl tetradecanoate

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
4.192902549666666

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.561713304317518

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.619245765321082

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968684336972288

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
84.90549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxypropyl tetradecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      34.484   9.129   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      35.818  11.439   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      38.485  12.979   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+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   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
1-Myristoyl glycerol	ChEBI
1-Tetradecanoylglycerol	ChEBI
Monomyristin	ChEBI
1-Monomyristin	MeSH
1-Monomyristin, (+-)-isomer	MeSH

Chemical Formula

C₁₇H₃₄O₄

Average Mass

302.4550 Da

Monoisotopic Mass

302.24571 Da

IUPAC Name

2,3-dihydroxypropyl tetradecanoate

Traditional Name

2,3-dihydroxypropyl tetradecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OCC(O)CO

InChI Identifier

InChI=1S/C17H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)21-15-16(19)14-18/h16,18-19H,2-15H2,1H3

InChI Key

DCBSHORRWZKAKO-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
Caenorhabditis elegans	LOTUS Database	35616633
Serenoa repens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

1-monoacylglycerols

Alternative Parents

Substituents

1-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-monoglyceride (CHEBI:75562 )

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	4.77	ALOGPS
logP	4.19	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	84.91 m³·mol⁻¹	ChemAxon
Polarizability	38.09 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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

79050

PDB ID

Not Available

ChEBI ID

75562

Good Scents ID

Not Available

References

General References

Showing NP-Card for Monomyristin (NP0137523)

MOL for NP0137523 (Monomyristin)

3D MOL for NP0137523 (Monomyristin)

3D SDF for NP0137523 (Monomyristin)

3D-SDF for NP0137523 (Monomyristin)

PDB for NP0137523 (Monomyristin)

3D PDB for NP0137523 (Monomyristin)

SMILES for NP0137523 (Monomyristin)

INCHI for NP0137523 (Monomyristin)

Structure for NP0137523 (Monomyristin)

3D Structure for NP0137523 (Monomyristin)