MiMeDB: Showing metabocard for 1-oleoyl-2-lyso-glycerone phosphate (MMDBc0047865)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:46:36 UTC

Update Date

2022-09-01 02:00:25 UTC

Metabolite ID

MMDBc0047865

Metabolite Identification

Common Name

1-oleoyl-2-lyso-glycerone phosphate

Description

1-oleoyl-2-lyso-glycerone phosphate, also known as 1-(9Z)-octadecenoyl-dhap(2-) or 1-(9Z)-octadecenoylglycerone 3-phosphate, belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position. 1-oleoyl-2-lyso-glycerone phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310061713382D          

 31 30  0  0  0  0            999 V2000
    7.0934    9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    3.6829    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.6506    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.8256    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 20  2  0  0  0  0
 23 21  2  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
 28 19  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 28  1  0  0  0  0
 30  9  1  0  0  0  0
 31 10  1  0  0  0  0
M  CHG  2  24  -1  25  -1
M  END


  Mrv1652310061713382D          

 31 30  0  0  0  0            999 V2000
    7.0934    9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    3.6829    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.6506    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.8256    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 20  2  0  0  0  0
 23 21  2  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
 28 19  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 28  1  0  0  0  0
 30  9  1  0  0  0  0
 31 10  1  0  0  0  0
M  CHG  2  24  -1  25  -1
M  END
> <DATABASE_ID>
MMDBc0047865

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OCC(=O)COP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10H,2-8,11-19H2,1H3,(H2,24,25,26)/p-2/b10-9-

> <INCHI_KEY>
YZKFNNQAEBNCEN-KTKRTIGZSA-L

> <FORMULA>
C21H37O7P

> <MOLECULAR_WEIGHT>
432.495

> <EXACT_MASS>
432.228787689

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.215239837648895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-3-(phosphonooxy)propyl (9Z)-octadec-9-enoate

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
5.796487260666666

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.21861561241517

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1885214774916144

> <JCHEM_PKA_STRONGEST_BASIC>
-7.034611009881403

> <JCHEM_POLAR_SURFACE_AREA>
115.79000000000002

> <JCHEM_REFRACTIVITY>
112.13869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxo-3-(phosphonooxy)propyl (9Z)-octadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-17         0                                  
HETATM    1  C   UNK     0      13.241  16.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.241  15.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.907  14.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907  13.035   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.574  12.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.574  10.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   9.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240   8.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.910   6.105   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      22.577   3.795   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      27.912   6.875   0.000  0.00  0.00           O-1
HETATM   25  O   UNK     0      27.348   4.771   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      25.808   7.438   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      19.909   5.335   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      25.244   5.335   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      26.578   6.105   0.000  0.00  0.00           P+0
HETATM   30  H   UNK     0       6.573   8.415   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.573   5.335   0.000  0.00  0.00           H+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   30                                                  
CONECT   10    9   11   31                                                  
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   21                                                       
CONECT   18   20   27                                                       
CONECT   19   20   28                                                       
CONECT   20   18   19   22                                                  
CONECT   21   17   23   27                                                  
CONECT   22   20                                                            
CONECT   23   21                                                            
CONECT   24   29                                                            
CONECT   25   29                                                            
CONECT   26   29                                                            
CONECT   27   18   21                                                       
CONECT   28   19   29                                                       
CONECT   29   24   25   26   28                                             
CONECT   30    9                                                            
CONECT   31   10                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

Synonyms

Value	Source
1-(9Z)-Octadecenoyl-dhap(2-)	ChEBI
1-(9Z)-Octadecenoylglycerone 3-phosphate	ChEBI
1-(9Z)-Octadecenoylglycerone 3-phosphate(2-)	ChEBI
1-(9Z)-Octadecenoylglycerone 3-phosphoric acid	Generator
1-(9Z)-Octadecenoylglycerone 3-phosphoric acid(2-)	Generator
1-Oleoyl-2-lyso-glycerone phosphoric acid	Generator
[3-[(Z)-Octadec-9-enoyl]oxy-2-oxopropyl] phosphoric acid	Generator

Molecular Formula

C₂₁H₃₇O₇P

Average Mass

432.495

Monoisotopic Mass

432.228787689

IUPAC Name

2-oxo-3-(phosphonooxy)propyl (9Z)-octadec-9-enoate

Traditional Name

2-oxo-3-(phosphonooxy)propyl (9Z)-octadec-9-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OCC(=O)COP([O-])([O-])=O

InChI Identifier

InChI=1S/C21H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10H,2-8,11-19H2,1H3,(H2,24,25,26)/p-2/b10-9-

InChI Key

YZKFNNQAEBNCEN-KTKRTIGZSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

O-acylglycerone-phosphates

Alternative Parents

Substituents

O-acylglycerone-phosphate
Monosaccharide phosphate
Fatty acid ester
Alpha-acyloxy ketone
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acylglycerone 3-phosphate(2-) (CHEBI:77492 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	5.79	ALOGPS
logP	5.8	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	115.79 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	112.14 m³·mol⁻¹	ChemAxon
Polarizability	48.22 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000900000-b928d87e1499e80b18d1	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-2110900000-973003f4c420aa490ab0	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9120000000-947217cc48421c905f2b	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-0737822f6f4ab33f16eb	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2240900000-c7aa77a49c9ba8812d73	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9040000000-8ad836ef81f1ebccce67	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

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

HMDB0155788

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

86289257

PDB ID

Not Available

ChEBI ID

77492

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-oleoyl-2-lyso-glycerone phosphate (MMDBc0047865)

MOL for #<Metabolite:0x00007fecae42f660>

3D MOL for #<Metabolite:0x00007fecae42f660>

3D SDF for #<Metabolite:0x00007fecae42f660>

3D-SDF for #<Metabolite:0x00007fecae42f660>

PDB for #<Metabolite:0x00007fecae42f660>

3D PDB for #<Metabolite:0x00007fecae42f660>

SMILES for #<Metabolite:0x00007fecae42f660>

INCHI for #<Metabolite:0x00007fecae42f660>

Structure for #<Metabolite:0x00007fecae42f660>

3D Structure for #<Metabolite:0x00007fecae42f660>