MiMeDB: Showing metabocard for Glycerol 1-monostearate (MMDBc0031702)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:45:00 UTC

Update Date

2024-04-30 19:51:32 UTC

Metabolite ID

MMDBc0031702

Metabolite Identification

Common Name

Glycerol 1-monostearate

Description

Glycerol 1-monostearate (GMS) is a member of the chemical class known as Monoacylglycerols. These are glycerides consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. It is an organic molecule used as an emulsifier. GMS is a colorless, odorless, and sweet-tasting flaky powder that is hygroscopic. It is a glycerol ester of stearic acid. GMS is a food additive used as a thickening, emulsifying, anti-caking, and preservative agent; an emulsifying agent for oils, waxes, and solvents; a protective coating for hygroscopic powders; a solidifier and control release agent in pharmaceuticals; and a resin lubricant. It is also used in cosmetics and hair care products. GMS is largely used in baking preparations to add "body" to the food.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214422D          

 25 24  0  0  0  0            999 V2000
    7.8609   -0.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1539   -0.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4317   -0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7232    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5732   -0.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    0.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    0.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -0.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4216    0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1424   -0.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495    0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -0.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2801    0.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0023   -0.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7095    0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1387    0.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8609   -0.1630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651    1.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4455   -1.0132    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  1  0  0  0  0
 15 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 24  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031702

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h20,22-23H,2-19H2,1H3

> <INCHI_KEY>
VBICKXHEKHSIBG-UHFFFAOYSA-N

> <FORMULA>
C21H42O4

> <MOLECULAR_WEIGHT>
358.5558

> <EXACT_MASS>
358.308309832

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
46.63217732266446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxypropyl octadecanoate

> <ALOGPS_LOGP>
6.73

> <JCHEM_LOGP>
5.971177209666667

> <ALOGPS_LOGS>
-5.52

> <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>
103.30949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glyceryl stearate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      14.674  -0.818   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.354  -0.024   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.006  -0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.683   0.024   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.338  -0.723   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.018   0.070   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.670  -0.676   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.350   0.117   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.000  -0.633   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.680   0.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.584   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.017   0.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.654   0.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.999  -0.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.319   0.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.667  -0.446   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.990   0.348   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.338  -0.399   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -10.658   0.394   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.003  -0.353   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.326   0.441   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -14.674  -0.304   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.962   1.891   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -12.032  -1.891   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                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   21                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

Synonyms

Value	Source
1-Octadecanoylglycerol	ChEBI
1-Stearoyl-glycerol	ChEBI
Glycerol 1-octadecanoate	ChEBI
Glyceryl monostearate	ChEBI
MAG(18:0)	ChEBI
MAG(18:0/0:0)	ChEBI
MG(18:0)	ChEBI
MG(18:0/0:0)	ChEBI
Glycerol 1-octadecanoic acid	Generator
Glyceryl monostearic acid	Generator
Glycerol 1-monostearic acid	Generator
(1)-2,3-Dihydroxypropyl stearate	HMDB
1,2,3-Propanetriol 1-octadecanoyl ester	HMDB
1,2,3-Propanetriol monooctadecanoate	HMDB
1,2,3-Propanetriol, homopolymer, isooctadecanoate	HMDB
1-Glyceryl stearate	HMDB
1-mono-Stearin	HMDB
1-Monooctadecanoyl-rac-glycerol	HMDB
1-Monostearin	HMDB
1-Monostearoylglycerol	HMDB
1-O-Octadecanoylglycerol	HMDB
1-O-Stearoylglycerol	HMDB
1-Stearoyl-rac-glycerol	HMDB
2,3-Dihydroxypropyl stearate	HMDB
3-Stearoyloxy-1,2-propanediol	HMDB
a-Monostearin	HMDB
alpha-Monostearin	HMDB
Cefatin	HMDB
Dermagine	HMDB
e471?	HMDB
FEMA 2527	HMDB
Glycerin 1-monostearate	HMDB
Glycerin 1-stearate	HMDB
Glycerol 1-monostearate	HMDB
Glycerol 1-stearate	HMDB
Glycerol alpha -monostearate	HMDB
Glycerol alpha -sterate	HMDB
Glycerol alpha-monostearate	HMDB
Glyceryl 1-monostearate	HMDB
Glyceryl-1-monostearate	HMDB
Octadecanoic acid 2,3-dihydroxypropyl ester	HMDB
Octadecanoic acid, 2,3-dihydroxypropyl ester	HMDB
Octadecanoic acid, ester with 1,2,3-propanetriol	HMDB
Stearic acid 1-monoglyceride	HMDB
Stearic acid alpha -monoglyceride	HMDB
Stearic acid alpha-monoglyceride	HMDB
Monostearin	MeSH

Molecular Formula

C₂₁H₄₂O₄

Average Mass

358.5558

Monoisotopic Mass

358.308309832

IUPAC Name

2,3-dihydroxypropyl octadecanoate

Traditional Name

glyceryl stearate

CAS Registry Number

123-94-4

SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO

InChI Identifier

InChI=1S/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h20,22-23H,2-19H2,1H3

InChI Key

VBICKXHEKHSIBG-UHFFFAOYSA-N

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:75555 )
monoacylglycerol 18:0 (CHEBI:75555 )
Monoacylglycerols (LMGL01010003 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	6.73	ALOGPS
logP	5.97	ChemAxon
logS	-5.5	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	20	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	46.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-007k-9530000000-e7c8759540fb484bf4af	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-2910000000-94597a6f353acb356316	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-000i-9670300000-c997fc24da788ae94c35	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-2580e940ca1f2f1cbca3	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-2580e940ca1f2f1cbca3	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0be6-0069000000-6f7c44088fdbecb9e384	2017-10-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0031075

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003078

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

24699

PDB ID

Not Available

ChEBI ID

75555

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. doi: 10.1096/fasebj.11.1.9034165. [PubMed:9034165 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Glycerol 1-monostearate (MMDBc0031702)

MOL for #<Metabolite:0x00007fecf0af8d88>

3D MOL for #<Metabolite:0x00007fecf0af8d88>

3D SDF for #<Metabolite:0x00007fecf0af8d88>

3D-SDF for #<Metabolite:0x00007fecf0af8d88>

PDB for #<Metabolite:0x00007fecf0af8d88>

3D PDB for #<Metabolite:0x00007fecf0af8d88>

SMILES for #<Metabolite:0x00007fecf0af8d88>

INCHI for #<Metabolite:0x00007fecf0af8d88>

Structure for #<Metabolite:0x00007fecf0af8d88>

3D Structure for #<Metabolite:0x00007fecf0af8d88>