MiMeDB: Showing metabocard for 1-O-Hexadecyl-2-O-acetyl-sn-glycerol (MMDBc0047889)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:47:42 UTC

Update Date

2022-09-01 02:00:39 UTC

Metabolite ID

MMDBc0047889

Metabolite Identification

Common Name

1-O-Hexadecyl-2-O-acetyl-sn-glycerol

Description

1-O-Hexadecyl-2-O-acetyl-sn-glycerol, also known as DG(O-16:0/2:0/0:0), belongs to the class of organic compounds known as 1-alkyl,2-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 2-positions through an ether and an ester linkage, respectively. 1-O-Hexadecyl-2-O-acetyl-sn-glycerol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572001311616262D          

 25 24  0  0  0  0            999 V2000
   -7.5019    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7874    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0730    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3585    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3585   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7874    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7874   -0.4125    0.0000 C   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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047889

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H42O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24-19-21(18-22)25-20(2)23/h21-22H,3-19H2,1-2H3/t21-/m0/s1

> <INCHI_KEY>
QTEHGUUSIIWOOW-NRFANRHFSA-N

> <FORMULA>
C21H42O4

> <MOLECULAR_WEIGHT>
358.563

> <EXACT_MASS>
358.308309832

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.726381901847766

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-(hexadecyloxy)-3-hydroxypropan-2-yl acetate

> <ALOGPS_LOGP>
6.83

> <JCHEM_LOGP>
5.903960886

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.578924731794302

> <JCHEM_PKA_STRONGEST_BASIC>
-2.982978322313171

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
103.50439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(hexadecyloxy)-3-hydroxypropan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-JAN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JAN-16         0                                  
HETATM    1  C   UNK     0     -14.004   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.670   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.336   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.003   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.669   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.002   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.668   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.001   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.334   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.668   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.335   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.003   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.003  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.336  -1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.336   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.670   0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.004   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.670  -0.770   0.000  0.00  0.00           C+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                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

Synonyms

Value	Source
1-O-Hexadecyl-2-acetyl-sn-glycerol	ChEBI
DG(O-16:0/2:0/0:0)	ChEBI
[(2S)-1-Hexadecoxy-3-hydroxypropan-2-yl] acetic acid	Generator
1-Palmityl-2-acetylglycerol	MeSH
1-Palmityl-2-acetylglycerol, (R)-isomer	MeSH
1-Palmityl-2-acetylglycerol, (S)-isomer	MeSH

Molecular Formula

C₂₁H₄₂O₄

Average Mass

358.563

Monoisotopic Mass

358.308309832

IUPAC Name

(2S)-1-(hexadecyloxy)-3-hydroxypropan-2-yl acetate

Traditional Name

(2S)-1-(hexadecyloxy)-3-hydroxypropan-2-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H42O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24-19-21(18-22)25-20(2)23/h21-22H,3-19H2,1-2H3/t21-/m0/s1

InChI Key

QTEHGUUSIIWOOW-NRFANRHFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,2-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 2-positions through an ether and an ester linkage, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1-alkyl,2-acylglycerols

Alternative Parents

Substituents

1-alkyl,2-acylglycerol
Glycerol ether
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-alkyl-2-acetylglycerol (CHEBI:75936 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00023 g/L	ALOGPS
logP	6.83	ALOGPS
logP	5.9	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	103.5 m³·mol⁻¹	ChemAxon
Polarizability	46.73 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02c7-9780000000-714af755f9b1a01cc07f	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3169000000-f12527b30ffc132c9a65	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00os-5593000000-9049bbd8624c85cf18e2	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01r6-9640000000-8b72627db2aeae7cdb23	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-5169000000-0e6c09f6cdc9aa72283e	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aou-8296000000-45999879d14f3166cf45	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9040000000-65b0e6e1e8e712aae40d	2016-09-14	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

11024766

PDB ID

Not Available

ChEBI ID

75936

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 1-O-Hexadecyl-2-O-acetyl-sn-glycerol (MMDBc0047889)

MOL for #<Metabolite:0x00007fdb0c997750>

3D MOL for #<Metabolite:0x00007fdb0c997750>

3D SDF for #<Metabolite:0x00007fdb0c997750>

3D-SDF for #<Metabolite:0x00007fdb0c997750>

PDB for #<Metabolite:0x00007fdb0c997750>

3D PDB for #<Metabolite:0x00007fdb0c997750>

SMILES for #<Metabolite:0x00007fdb0c997750>

INCHI for #<Metabolite:0x00007fdb0c997750>

Structure for #<Metabolite:0x00007fdb0c997750>

3D Structure for #<Metabolite:0x00007fdb0c997750>