MiMeDB: Showing metabocard for 1-hexadecanoyl-sn-glycero-3-phospho-L-serine (MMDBc0055111)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:43:42 UTC

Update Date

2022-08-12 20:09:14 UTC

Metabolite ID

MMDBc0055111

Metabolite Identification

Common Name

1-hexadecanoyl-sn-glycero-3-phospho-L-serine

Description

1-palmitoyl-sn-glycero-3-phosphoserine(1-), also known as 1-C16:0-lysophosphatidylserine(1-), belongs to the class of organic compounds known as 1-acyl-glycerol-3-phosphoserines. These are monoacylglycerol-3-phosphoserines with a fatty acyl chain linked to the O1-atom of the glycerol moiety. Based on a literature review very few articles have been published on 1-palmitoyl-sn-glycero-3-phosphoserine(1-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221432D          

 35 34  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
   23.6664    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
   24.3809    5.8263    0.0000 C   0  0  1  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
   25.0953    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3809    6.6513    0.0000 N   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
   25.8098    5.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0953    4.5888    0.0000 O   0  5  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
   22.9519    5.8263    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
   24.3809    5.0013    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
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 15  1  0  0  0  0
 22 20  1  0  0  0  0
 20 23  1  1  0  0  0
 19 24  1  1  0  0  0
 25 21  2  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 30 16  1  0  0  0  0
 30 21  1  0  0  0  0
 31 17  1  0  0  0  0
 32 18  1  0  0  0  0
 33 28  1  0  0  0  0
 33 29  2  0  0  0  0
 33 31  1  0  0  0  0
 33 32  1  0  0  0  0
 19 34  1  1  0  0  0
 20 35  1  1  0  0  0
M  CHG  1  27  -1
M  END


  Mrv1652306172221432D          

 35 34  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
   23.6664    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
   24.3809    5.8263    0.0000 C   0  0  1  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
   25.0953    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3809    6.6513    0.0000 N   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
   25.8098    5.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0953    4.5888    0.0000 O   0  5  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
   22.9519    5.8263    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
   24.3809    5.0013    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
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 15  1  0  0  0  0
 22 20  1  0  0  0  0
 20 23  1  1  0  0  0
 19 24  1  1  0  0  0
 25 21  2  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 30 16  1  0  0  0  0
 30 21  1  0  0  0  0
 31 17  1  0  0  0  0
 32 18  1  0  0  0  0
 33 28  1  0  0  0  0
 33 29  2  0  0  0  0
 33 31  1  0  0  0  0
 33 32  1  0  0  0  0
 19 34  1  1  0  0  0
 20 35  1  1  0  0  0
M  CHG  1  27  -1
M  END
> <DATABASE_ID>
MMDBc0055111

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H44NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(25)30-16-19(24)17-31-33(28,29)32-18-20(23)22(26)27/h19-20,24H,2-18,23H2,1H3,(H,26,27)(H,28,29)/p-1/t19-,20+/m1/s1

> <INCHI_KEY>
XIVOBOJQPNEUSC-UXHICEINSA-M

> <FORMULA>
C22H43NO9P

> <MOLECULAR_WEIGHT>
496.558

> <EXACT_MASS>
496.268092547

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.999557943218065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)propanoate

> <JCHEM_LOGP>
2.6124365290915454

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.213428710915933

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5080063842116909

> <JCHEM_PKA_STRONGEST_BASIC>
9.376581814113422

> <JCHEM_POLAR_SURFACE_AREA>
168.43999999999997

> <JCHEM_REFRACTIVITY>
134.07949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}propanoate

> <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      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      44.177  10.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.509   9.336   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.511  10.876   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.845  10.106   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      45.511  12.416   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      37.509   7.796   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      33.508  11.646   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      48.178  10.876   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      46.845   8.566   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      42.280   8.772   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      40.740  11.439   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      34.842   9.336   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      40.176   9.336   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      42.844  10.876   0.000  0.00  0.00           O+0
HETATM   33  P   UNK     0      41.510  10.106   0.000  0.00  0.00           P+0
HETATM   34  H   UNK     0      37.509  10.876   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      45.511   9.336   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   21                                                       
CONECT   16   19   30                                                       
CONECT   17   19   31                                                       
CONECT   18   20   32                                                       
CONECT   19   16   17   24   34                                             
CONECT   20   18   22   23   35                                             
CONECT   21   15   25   30                                                  
CONECT   22   20   26   27                                                  
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25   21                                                            
CONECT   26   22                                                            
CONECT   27   22                                                            
CONECT   28   33                                                            
CONECT   29   33                                                            
CONECT   30   16   21                                                       
CONECT   31   17   33                                                       
CONECT   32   18   33                                                       
CONECT   33   28   29   31   32                                             
CONECT   34   19                                                            
CONECT   35   20                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END

Synonyms

Value	Source
1-C16:0-Lysophosphatidylserine(1-)	ChEBI
1-Hexadecanoyl-sn-glycero-3-phospho-L-serine	ChEBI
1-Hexadecanoyl-sn-glycero-3-phosphoserine(1-)	ChEBI

Molecular Formula

C₂₂H₄₃NO₉P

Average Mass

496.558

Monoisotopic Mass

496.268092547

IUPAC Name

(2S)-2-amino-3-({[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)propanoate

Traditional Name

(2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}propanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H44NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(25)30-16-19(24)17-31-33(28,29)32-18-20(23)22(26)27/h19-20,24H,2-18,23H2,1H3,(H,26,27)(H,28,29)/p-1/t19-,20+/m1/s1

InChI Key

XIVOBOJQPNEUSC-UXHICEINSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-glycerol-3-phosphoserines. These are monoacylglycerol-3-phosphoserines with a fatty acyl chain linked to the O1-atom of the glycerol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoserines

Direct Parent

1-acyl-glycerol-3-phosphoserines

Alternative Parents

Substituents

1-monoacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Fatty acyl
Phosphoric acid ester
Alkyl phosphate
Amino acid or derivatives
Amino acid
Carboxylic acid salt
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Alcohol
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Organic salt
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysophosphatidylserine 16:0(1-) (CHEBI:75020 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.61	ChemAxon
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	168.44 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	134.08 m³·mol⁻¹	ChemAxon
Polarizability	54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

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

29368469

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57689794

PDB ID

Not Available

ChEBI ID

75020

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-phospho-L-serine (MMDBc0055111)

MOL for #<Metabolite:0x00007fdb701b7238>

3D MOL for #<Metabolite:0x00007fdb701b7238>

3D SDF for #<Metabolite:0x00007fdb701b7238>

3D-SDF for #<Metabolite:0x00007fdb701b7238>

PDB for #<Metabolite:0x00007fdb701b7238>

3D PDB for #<Metabolite:0x00007fdb701b7238>

SMILES for #<Metabolite:0x00007fdb701b7238>

INCHI for #<Metabolite:0x00007fdb701b7238>

Structure for #<Metabolite:0x00007fdb701b7238>

3D Structure for #<Metabolite:0x00007fdb701b7238>