Showing metabocard for O-Phosphoethanolamine (MMDBc0030363)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:05:21 UTC
Update Date2024-10-15 20:23:04 UTC
Metabolite IDMMDBc0030363
Metabolite Identification
Common NameO-Phosphoethanolamine
DescriptionPhosphoethanolamine is chemically the ethanolamine mono-ester of phosphoric acid. It is an important intermediate in the synthesis of LPS. In particular, phosphoethanolamine (pEtN) is added to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A via phosphoethanolamine transferase (eptB).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb71d14968>


  Mrv1652309032023572D          

  8  7  0  0  0  0            999 V2000
   11.8291  -13.0248    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.5436  -12.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1146  -13.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4166  -12.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2416  -13.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6871  -13.0248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2581  -13.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9725  -12.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb71d14968>

HMDB0000224
     RDKit          3D
O-Phosphoethanolamine
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.2447    0.7162    0.4850 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246   -0.2795   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.9499    0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008   -0.0409    0.9477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823   -0.0107    0.1254 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2036   -1.4182   -0.2876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6539    0.9608   -1.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0875    0.6905    1.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.4208   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    0.3483    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -1.0701   -0.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2516    0.2174   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -1.5110   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671   -1.7150    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102    1.7910   -0.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791    0.8502    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb71d14968>


  Mrv1652309032023572D          

  8  7  0  0  0  0            999 V2000
   11.8291  -13.0248    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.5436  -12.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1146  -13.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4166  -12.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2416  -13.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6871  -13.0248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2581  -13.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9725  -12.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030363

> <DATABASE_NAME>
MIME

> <SMILES>
NCCOP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

> <INCHI_KEY>
SUHOOTKUPISOBE-UHFFFAOYSA-N

> <FORMULA>
C2H8NO4P

> <MOLECULAR_WEIGHT>
141.063

> <EXACT_MASS>
141.019094261

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.11675089618825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)phosphonic acid

> <ALOGPS_LOGP>
-1.54

> <JCHEM_LOGP>
-2.4512986210264835

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.565826815298373

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5391795005429323

> <JCHEM_PKA_STRONGEST_BASIC>
10.017192603268537

> <JCHEM_POLAR_SURFACE_AREA>
92.77999999999999

> <JCHEM_REFRACTIVITY>
27.084

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphorylethanolamine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb71d14968>

HMDB0000224
     RDKit          3D
O-Phosphoethanolamine
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.2447    0.7162    0.4850 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246   -0.2795   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.9499    0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008   -0.0409    0.9477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823   -0.0107    0.1254 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2036   -1.4182   -0.2876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6539    0.9608   -1.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0875    0.6905    1.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.4208   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    0.3483    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -1.0701   -0.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2516    0.2174   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -1.5110   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671   -1.7150    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102    1.7910   -0.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791    0.8502    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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PDB for #<Metabolite:0x00007fdb71d14968>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  P   UNK     0      22.081 -24.313   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      23.415 -23.543   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      20.747 -25.083   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      21.311 -22.979   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      22.851 -25.647   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      27.416 -24.313   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      24.748 -24.313   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.082 -23.543   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    7                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    8                                                            
CONECT    7    2    8                                                       
CONECT    8    6    7                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x00007fdb71d14968>

COMPND    HMDB0000224
HETATM    1  N1  UNL     1       2.245   0.716   0.485  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.625  -0.279  -0.346  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.444  -0.950   0.312  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.401  -0.041   0.948  1.00  0.00           O  
HETATM    5  P1  UNL     1      -1.882  -0.011   0.125  1.00  0.00           P  
HETATM    6  O2  UNL     1      -2.204  -1.418  -0.288  1.00  0.00           O  
HETATM    7  O3  UNL     1      -1.654   0.961  -1.251  1.00  0.00           O  
HETATM    8  O4  UNL     1      -3.087   0.691   1.066  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.683   1.421  -0.166  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.045   0.348   1.055  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.346  -1.070  -0.628  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.252   0.217  -1.269  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.088  -1.511  -0.498  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.767  -1.715   1.039  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.210   1.791  -0.913  1.00  0.00           H  
HETATM   16  H8  UNL     1      -3.879   0.850   0.513  1.00  0.00           H  
CONECT    1    2    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5
CONECT    5    6    6    7    8
CONECT    7   15
CONECT    8   16
END
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SMILES for #<Metabolite:0x00007fdb71d14968>

NCCOP(O)(O)=O
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INCHI for #<Metabolite:0x00007fdb71d14968>

InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
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Synonyms
ValueSource
2-Amino-ethanol dihydrogen phosphateChEBI
2-Amino-ethanol phosphateChEBI
Colamine phosphateChEBI
Colamine phosphoric acidChEBI
Colaminphosphoric acidChEBI
EAPChEBI
Ethanolamine acid phosphateChEBI
Ethanolamine O-phosphateChEBI
Ethanolamine phosphateChEBI
mono(2-Aminoethyl) phosphateChEBI
Monoaminoethyl phosphateChEBI
O-PhosphocolamineChEBI
O-PhosphorylethanolamineChEBI
OPEChEBI
PEChEBI
PEAChEBI
PETNChEBI
PhosphoethanolamineChEBI
Phosphoric acid 2-aminoethyl phenyl esterChEBI
Phosphoryl-ethanolamineChEBI
2-Amino-ethanol dihydrogen phosphoric acidGenerator
2-Amino-ethanol phosphoric acidGenerator
ColaminphosphateGenerator
Ethanolamine acid phosphoric acidGenerator
Ethanolamine O-phosphoric acidGenerator
Ethanolamine phosphoric acidGenerator
mono(2-Aminoethyl) phosphoric acidGenerator
Monoaminoethyl phosphoric acidGenerator
Phosphate 2-aminoethyl phenyl esterGenerator
PhosphonoethanolamineHMDB
2-Amino-ethanol dihydrogen phosphate (ester)HMDB
2-Aminoethanol O-phosphateHMDB
2-Aminoethyl dihydrogen phosphateHMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)HMDB
2-Aminoethyl phosphateHMDB
Colamine acid phosphateHMDB
Colaminephosphoric acidHMDB
EthampHMDB
O-PhosphonatoethanaminiumHMDB
PhosphoryethanolamineHMDB
PhosphorylethanolamineHMDB
Phosphorylethanolamine, 3H-labeled CPDHMDB
Phosphorylethanolamine magnesium (1:1) saltHMDB
Phosphorylethanolamine zinc saltHMDB
Phosphorylethanolamine, cobalt (2+) (1:1) saltHMDB
Calcium 2-aminoethanol phosphateHMDB
Phosphorylethanolamine ca (1:1) saltHMDB
Molecular FormulaC2H8NO4P
Average Mass141.063
Monoisotopic Mass141.019094261
IUPAC Name(2-aminoethoxy)phosphonic acid
Traditional Namephosphorylethanolamine
CAS Registry Number1071-23-4
SMILES
NCCOP(O)(O)=O
InChI Identifier
InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
InChI KeySUHOOTKUPISOBE-UHFFFAOYSA-N