MiMeDB: Showing metabocard for MG(16:1(9Z/0:0)/0:0/0:0) (MMDBc0045190)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 13:36:51 UTC

Update Date

2022-09-01 00:59:24 UTC

Metabolite ID

MMDBc0045190

Metabolite Identification

Common Name

MG(16:1(9Z/0:0)/0:0/0:0)

Description

MG(16:1(9Z/0:0)/0:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups: 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. MG(16:1(9Z/0:0)/0:0/0:0), in particular, consists of one 9Z-hexadecenoyl chain at the C-1 position.

Structure

MOL SDF PDB SMILES InChI

1-(9Z-hexadecenoyl)-sn-glycerol MG(16:1(9Z)/0:0/0:0)
  Mrv1652307071619222D          

 24 23  0  0  1  0            999 V2000
   24.1443   -6.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1832   -7.0352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2219   -6.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1442   -5.3703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2606   -7.0352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4330   -8.1452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9384   -8.1590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4298   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4298   -4.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7156   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0015   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2873   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5732   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8591   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1450   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4308   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7167   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8916   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1775   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4633   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7492   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0351   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3210   -5.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6068   -4.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  8  1  0  0  0  0
  5  3  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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  2  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0045190

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CO)COC(=O)CCCCCCC\C=C/CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C19H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h7-8,18,20-21H,2-6,9-17H2,1H3/b8-7-/t18-/m1/s1

> <INCHI_KEY>
KVYUBFKSKZWZSV-JTHGQSKGSA-N

> <FORMULA>
C19H36O4

> <MOLECULAR_WEIGHT>
328.493

> <EXACT_MASS>
328.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.873337108381826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2,3-dihydroxypropyl (9Z)-hexadec-9-enoate

> <ALOGPS_LOGP>
5.22

> <JCHEM_LOGP>
4.720118223

> <ALOGPS_LOGS>
-4.75

> <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>
66.75999999999999

> <JCHEM_REFRACTIVITY>
95.22409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-dihydroxypropyl (9Z)-hexadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUL-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1-(9Z-hexadecenoyl)-sn-glycerol MG(16:1(9Z)/0:0/0:
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-16         0                                  
HETATM    1  C   UNK     0      45.069 -12.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.275 -13.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.481 -12.097   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      45.069 -10.025   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      39.686 -13.132   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      41.875 -15.204   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      44.685 -15.230   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      43.736  -9.255   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      43.736  -7.815   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      42.403 -10.026   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.070  -9.255   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.736 -10.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.403  -9.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.070 -10.026   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.737  -9.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.404 -10.026   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.071  -9.255   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.531  -9.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.198 -10.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.865  -9.255   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.532 -10.026   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.199  -9.255   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.866 -10.026   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.533  -9.255   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    6    7    3                                             
CONECT    3    2    5                                                       
CONECT    4    1    8                                                       
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   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                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Not Available

Molecular Formula

C₁₉H₃₆O₄

Average Mass

328.493

Monoisotopic Mass

328.261359639

IUPAC Name

(2R)-2,3-dihydroxypropyl (9Z)-hexadec-9-enoate

Traditional Name

(2R)-2,3-dihydroxypropyl (9Z)-hexadec-9-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CO)COC(=O)CCCCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C19H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h7-8,18,20-21H,2-6,9-17H2,1H3/b8-7-/t18-/m1/s1

InChI Key

KVYUBFKSKZWZSV-JTHGQSKGSA-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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0059 g/L	ALOGPS
logP	5.22	ALOGPS
logP	4.72	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	17	ChemAxon
Refractivity	95.22 m³·mol⁻¹	ChemAxon
Polarizability	40.87 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001s-9003000000-1606f046035b071e3e2e	2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

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

53301862

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rattray JB, Schibeci A, Kidby DK: Lipids of yeasts. Bacteriol Rev. 1975 Sep;39(3):197-231. doi: 10.1128/br.39.3.197-231.1975. [PubMed:240350 ]

Showing metabocard for MG(16:1(9Z/0:0)/0:0/0:0) (MMDBc0045190)

MOL for #<Metabolite:0x00007fdb708486d8>

3D MOL for #<Metabolite:0x00007fdb708486d8>

3D SDF for #<Metabolite:0x00007fdb708486d8>

3D-SDF for #<Metabolite:0x00007fdb708486d8>

PDB for #<Metabolite:0x00007fdb708486d8>

3D PDB for #<Metabolite:0x00007fdb708486d8>

SMILES for #<Metabolite:0x00007fdb708486d8>

INCHI for #<Metabolite:0x00007fdb708486d8>

Structure for #<Metabolite:0x00007fdb708486d8>

3D Structure for #<Metabolite:0x00007fdb708486d8>