MiMeDB: Showing metabocard for 1-hexadecanoyl-sn-glycero-3-phosphate (MMDBc0054121)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:54:11 UTC

Update Date

2022-09-01 02:27:25 UTC

Metabolite ID

MMDBc0054121

Metabolite Identification

Common Name

1-hexadecanoyl-sn-glycero-3-phosphate

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221922282D          

 28 27  0  0  1  0            999 V2000
    7.2336    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
    8.6625    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
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9519    5.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6499    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8249    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2374    5.4138    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    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
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 18 20  1  1  0  0  0
 21 19  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  2  0  0  0  0
 27 26  1  0  0  0  0
 18 28  1  1  0  0  0
M  END


  Mrv1652305221922282D          

 28 27  0  0  1  0            999 V2000
    7.2336    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
    8.6625    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
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    5.0013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9519    5.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6499    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8249    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5230    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2374    5.4138    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0940    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
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 18 20  1  1  0  0  0
 21 19  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  2  0  0  0  0
 27 26  1  0  0  0  0
 18 28  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054121

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)/t18-/m1/s1

> <INCHI_KEY>
YNDYKPRNFWPPFU-GOSISDBHSA-N

> <FORMULA>
C19H39O7P

> <MOLECULAR_WEIGHT>
410.4825

> <EXACT_MASS>
410.243340114

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.9338336872712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
4.958473848333334

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
104.98039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      13.503   9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.836  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      17.504  10.106   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.840  10.106   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.175  10.106   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.843  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.509   9.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      37.509   7.796   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      33.508  11.646   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      42.844  10.876   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      42.280   8.772   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      40.740  11.439   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      34.842   9.336   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      40.176   9.336   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0      41.510  10.106   0.000  0.00  0.00           P+0
HETATM   28  H   UNK     0      37.509  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   19                                                       
CONECT   16   18   25                                                       
CONECT   17   18   26                                                       
CONECT   18   16   17   20   28                                             
CONECT   19   15   21   25                                                  
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22   27                                                            
CONECT   23   27                                                            
CONECT   24   27                                                            
CONECT   25   16   19                                                       
CONECT   26   17   27                                                       
CONECT   27   22   23   24   26                                             
CONECT   28   18                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

Synonyms

Value	Source
(2R)-2-Hydroxy-3-(phosphonooxy)propyl palmitate	ChEBI
1-Hexadecanoyl-sn-glycero-3-phosphate	ChEBI
1-Palmitoylglycerol 3-phosphate	ChEBI
LPA(16:0/0:0)	ChEBI
LysoPA(16:0/0:0)	ChEBI
Lysophosphatidic acid(16:0)	ChEBI
Lysophosphatidic acid(16:0/0:0)	ChEBI
(2R)-2-Hydroxy-3-(phosphonooxy)propyl palmitic acid	Generator
1-Hexadecanoyl-sn-glycero-3-phosphoric acid	Generator
1-Palmitoylglycerol 3-phosphoric acid	Generator
Lysophosphatidate(16:0)	Generator
Lysophosphatidate(16:0/0:0)	Generator
1-Palmitoyl-rac-glycerol 3-phosphate	MeSH
1-Palmitoyl-lysophosphatidic acid, sodium salt, (R)-isomer	MeSH
1-Palmitoyl-sn-glycerol 3-phosphate	MeSH
PLPA	MeSH
1-Palmitoyl-lysophosphatidic acid	MeSH
1-Palmitoyl-lysophosphatidic acid, (R)-isomer	MeSH

Molecular Formula

C₁₉H₃₉O₇P

Average Mass

410.4825

Monoisotopic Mass

410.243340114

IUPAC Name

[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(O)=O

InChI Identifier

InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)/t18-/m1/s1

InChI Key

YNDYKPRNFWPPFU-GOSISDBHSA-N

Chemical Taxonomy

Description

This compound belongs to the class of chemical entities known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Lipids and lipid-like molecules

Sub Class

Glycerophospholipids

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol 3-phosphate (CHEBI:15799 )
1-palmitoylglycerol 3-phosphate (CHEBI:15799 )
Monoacylglycerophosphates (LMGP10050006 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	3.87	ALOGPS
logP	4.96	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	104.98 m³·mol⁻¹	ChemAxon
Polarizability	46.93 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

Not Available

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
MMDBr0025537	1-hexadecanoyl-sn-glycero-3-phosphate	PA(16:0/16:0)	1-acyl-sn-glycerol-3-phosphate acyltransferase	Acylation	RHEA	34755880
MMDBr0025538	1-hexadecanoyl-sn-glycero-3-phosphate	PA(16:0/16:0)	1-acyl-sn-glycerol-3-phosphate acyltransferase	Acylation	RHEA	34755880

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
Eukaryota/Fungi	Ascomycota	2
Bacteria	Proteobacteria	1
Bacteria/Eubacteria	Firmicutes	1	Human

Exposure Sources

Other Exposures

Source Type	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

HMDB07853

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

6419701

PDB ID

NKO

ChEBI ID

15799

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-hexadecanoyl-sn-glycero-3-phosphate (MMDBc0054121)

MOL for #<Metabolite:0x00007f91fa4a3268>

3D MOL for #<Metabolite:0x00007f91fa4a3268>

3D SDF for #<Metabolite:0x00007f91fa4a3268>

3D-SDF for #<Metabolite:0x00007f91fa4a3268>

PDB for #<Metabolite:0x00007f91fa4a3268>

3D PDB for #<Metabolite:0x00007f91fa4a3268>

SMILES for #<Metabolite:0x00007f91fa4a3268>

INCHI for #<Metabolite:0x00007f91fa4a3268>

Structure for #<Metabolite:0x00007f91fa4a3268>

3D Structure for #<Metabolite:0x00007f91fa4a3268>