MiMeDB: Showing metabocard for 1-O-hexadecyl-sn-glycero-3-phosphate (MMDBc0055118)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:43:53 UTC

Update Date

2022-08-12 20:09:14 UTC

Metabolite ID

MMDBc0055118

Metabolite Identification

Common Name

1-O-hexadecyl-sn-glycero-3-phosphate

Description

1-hexadecyl-sn-glycero-3-phosphate(2-) belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond. Based on a literature review very few articles have been published on 1-hexadecyl-sn-glycero-3-phosphate(2-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221432D          

 27 26  0  0  1  0            999 V2000
  -10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5191    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8046    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0901    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6612    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7690    5.0013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7690    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    5.8263    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.3249    4.6993    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.4999    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124    5.4138    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7690    5.8263    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  1  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
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  1  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  2  0  0  0  0
 26 25  1  0  0  0  0
 19 27  1  1  0  0  0
M  CHG  2  21  -1  22  -1
M  END


  Mrv1652306172221432D          

 27 26  0  0  1  0            999 V2000
  -10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5191    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8046    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0901    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6612    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7690    5.0013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7690    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    5.8263    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.3249    4.6993    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.4999    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124    5.4138    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7690    5.8263    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  1  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
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  1  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  2  0  0  0  0
 26 25  1  0  0  0  0
 19 27  1  1  0  0  0
M  CHG  2  21  -1  22  -1
M  END
> <DATABASE_ID>
MMDBc0055118

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H41O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24-17-19(20)18-25-26(21,22)23/h19-20H,2-18H2,1H3,(H2,21,22,23)/p-2/t19-/m1/s1

> <INCHI_KEY>
XLVRFPVHQPHXAA-LJQANCHMSA-L

> <FORMULA>
C19H39O6P

> <MOLECULAR_WEIGHT>
394.49

> <EXACT_MASS>
394.249523134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.998509868511576

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-1-(hexadecyloxy)-3-(phosphonooxy)propan-2-ol

> <JCHEM_LOGP>
5.339269444333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.532823087649438

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5070267056744795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3931742588163853

> <JCHEM_POLAR_SURFACE_AREA>
101.88000000000001

> <JCHEM_REFRACTIVITY>
102.98239999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-1-(hexadecyloxy)-3-(phosphonooxy)propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0     -18.837   9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.504  10.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -16.170   9.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.836  10.106   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.503   9.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.169  10.106   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.835   9.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.502  10.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.168   9.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.834  10.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.501   9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.167  10.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.833   9.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.500  10.106   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.166   9.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.168  10.106   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.835  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.503  10.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.169   9.336   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.169   7.796   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.504  10.876   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0       9.940   8.772   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0       8.400  11.439   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.502   9.336   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.836   9.336   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0       9.170  10.106   0.000  0.00  0.00           P+0
HETATM   27  H   UNK     0       5.169  10.876   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                                                       
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   24                                                       
CONECT   17   19   24                                                       
CONECT   18   19   25                                                       
CONECT   19   17   18   20   27                                             
CONECT   20   19                                                            
CONECT   21   26                                                            
CONECT   22   26                                                            
CONECT   23   26                                                            
CONECT   24   16   17                                                       
CONECT   25   18   26                                                       
CONECT   26   21   22   23   25                                             
CONECT   27   19                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

Synonyms

Value	Source
1-O-Hexadecyl-sn-glycero-3-phosphate	ChEBI
1-O-Hexadecyl-sn-glycerol 3-phosphate(2-)	ChEBI
1-O-Hexadecyl-sn-glycero-3-phosphoric acid	Generator
1-O-Hexadecyl-sn-glycerol 3-phosphoric acid(2-)	Generator
1-Hexadecyl-sn-glycero-3-phosphoric acid(2-)	Generator

Molecular Formula

C₁₉H₃₉O₆P

Average Mass

394.49

Monoisotopic Mass

394.249523134

IUPAC Name

(2R)-1-(hexadecyloxy)-3-(phosphonooxy)propan-2-ol

Traditional Name

(2R)-1-(hexadecyloxy)-3-(phosphonooxy)propan-2-ol

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP([O-])([O-])=O

InChI Identifier

InChI=1S/C19H41O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24-17-19(20)18-25-26(21,22)23/h19-20H,2-18H2,1H3,(H2,21,22,23)/p-2/t19-/m1/s1

InChI Key

XLVRFPVHQPHXAA-LJQANCHMSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

Monoalkylglycerophosphates

Alternative Parents

Substituents

Monoalkylglycerophosphate
Glycerol ether
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-alkyl-sn-glycerol 3-phosphate(2-) (CHEBI:77580 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	5.34	ChemAxon
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.88 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	47 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	Deposition Date	View
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

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
Bacteria	Actinobacteria	3	Human ; Human feces; Human nasopharyngeal swab

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

31150335

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86289280

PDB ID

Not Available

ChEBI ID

77580

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 1-O-hexadecyl-sn-glycero-3-phosphate (MMDBc0055118)

MOL for #<Metabolite:0x00007fdb487aab40>

3D MOL for #<Metabolite:0x00007fdb487aab40>

3D SDF for #<Metabolite:0x00007fdb487aab40>

3D-SDF for #<Metabolite:0x00007fdb487aab40>

PDB for #<Metabolite:0x00007fdb487aab40>

3D PDB for #<Metabolite:0x00007fdb487aab40>

SMILES for #<Metabolite:0x00007fdb487aab40>

INCHI for #<Metabolite:0x00007fdb487aab40>

Structure for #<Metabolite:0x00007fdb487aab40>

3D Structure for #<Metabolite:0x00007fdb487aab40>