MiMeDB: Showing metabocard for 1-monohexadecanoylglycerol (MMDBc0034221)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:21:17 UTC

Update Date

2022-08-31 22:45:24 UTC

Metabolite ID

MMDBc0034221

Metabolite Identification

Common Name

1-monohexadecanoylglycerol

Description

1-monohexadecanoylglycerol, also known as (R)-1-monopalmitin or sn-glycerol 3-palmitate, belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position. 1-monohexadecanoylglycerol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 06081214512D          

 23 22  0  0  1  0            999 V2000
   10.4230    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4243    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1388    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8533    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5677    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2822    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1401    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1401    5.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8546    6.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5690    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    6.8427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.9980    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    6.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    7.6677    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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  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
 20 23  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0034221

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3/t18-/m1/s1

> <INCHI_KEY>
QHZLMUACJMDIAE-GOSISDBHSA-N

> <FORMULA>
C19H38O4

> <MOLECULAR_WEIGHT>
330.5026

> <EXACT_MASS>
330.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
42.38853185760943

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2,3-dihydroxypropyl hexadecanoate

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.082039879666667

> <ALOGPS_LOGS>
-4.85

> <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>
94.10749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-dihydroxypropyl hexadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-12         0                                  
HETATM    1  C   UNK     0      19.456  12.773   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.124  12.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.457  12.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.791  12.773   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.125  12.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.458  12.773   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.792  12.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.126  12.773   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.459  12.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.793  12.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.127  12.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.460  12.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.794  12.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.128  12.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.462  12.003   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      39.462  10.463   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      40.795  12.773   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      42.129  12.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.463  12.773   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.796  12.003   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      46.130  12.773   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      43.463  14.313   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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

Synonyms

Value	Source
(2R)-2,3-Dihydroxypropyl palmitate	ChEBI
(R)-1-Monopalmitin	ChEBI
(R)-2,3-Dihydroxypropyl N-hexadecanoate	ChEBI
3-Hexadecanoyl-sn-glycerol	ChEBI
sn-Glycerol 3-palmitate	ChEBI
(2R)-2,3-Dihydroxypropyl palmitic acid	Generator
(R)-2,3-Dihydroxypropyl N-hexadecanoic acid	Generator
sn-Glycerol 3-palmitic acid	Generator
Palmitoyl glycerol	MeSH
Palmitoyl glycerol, (+,-)-isomer	MeSH
Palmitoyl glycerol, hexadecanoic-1-(14)C-labeled CPD, (R)-isomer	MeSH
rac-1(3)-Palmitoyl glycerol	MeSH
1-Monohexadecanoyl-rac-glycerol	MeSH
1-Monopalmitin	MeSH
1-Glyceryl hexadecanoate	MeSH
1-Monohexadecanoylglycerol	MeSH

Molecular Formula

C₁₉H₃₈O₄

Average Mass

330.5026

Monoisotopic Mass

330.277009704

IUPAC Name

(2R)-2,3-dihydroxypropyl hexadecanoate

Traditional Name

(2R)-2,3-dihydroxypropyl hexadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](O)CO

InChI Identifier

InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3/t18-/m1/s1

InChI Key

QHZLMUACJMDIAE-GOSISDBHSA-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

3-acyl-sn-glycerol (CHEBI:64757 )
1-monopalmitoylglycerol (CHEBI:64757 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0047 g/L	ALOGPS
logP	5.73	ALOGPS
logP	5.08	ChemAxon
logS	-4.8	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	18	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	42.39 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9351000000-f2f6a9e7c360a0c0a5b4	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-003r-6149000000-46e003ac9032083459dc	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9231000000-984ad8a5384b8670209d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056u-9420000000-2b1d5a640ca0c7b0f0d0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a70-2094000000-2727de3f777ddd17bb39	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-4090000000-3e968d1b6b44f5a6c1e4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9060000000-9cc1ac16deaed570ab82	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Not Available

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

11359451

PDB ID

Not Available

ChEBI ID

64757

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]

Showing metabocard for 1-monohexadecanoylglycerol (MMDBc0034221)

MOL for #<Metabolite:0x00007fece05db068>

3D MOL for #<Metabolite:0x00007fece05db068>

3D SDF for #<Metabolite:0x00007fece05db068>

3D-SDF for #<Metabolite:0x00007fece05db068>

PDB for #<Metabolite:0x00007fece05db068>

3D PDB for #<Metabolite:0x00007fece05db068>

SMILES for #<Metabolite:0x00007fece05db068>

INCHI for #<Metabolite:0x00007fece05db068>

Structure for #<Metabolite:0x00007fece05db068>

3D Structure for #<Metabolite:0x00007fece05db068>