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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-04-04 16:09:28 UTC

Update Date

2022-09-22 17:44:16 UTC

HMDB ID

HMDB0240345

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N2,N5-Diacetylornithine

Description

N2,N5-Diacetylornithine, also known as bisorcic, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N2,N5-Diacetylornithine is an N-acetyl-L-amino acid that is L-ornithine carrying two acetyl substituents at positions N-2 and N-5. N2,N5-Diacetylornithine was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0240345
     RDKit          3D
N2,N5-Diacetylornithine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -5.5657    0.2901    0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -0.3986    0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2849   -1.6244    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.3227    0.5432 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8541   -0.3875    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    0.5358    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -0.3505    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    0.4210    0.0205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9051   -0.5264   -0.2606 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -0.3446   -1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -1.2407   -1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3964    0.6120   -2.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    1.1053    1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822    0.7716    1.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.0914    1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0336    0.5725   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2754   -0.3363    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4503    1.2353    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763    1.3425    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -1.1712    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.8609   -0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431    1.3575   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    0.9637    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -0.8266   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -1.1623    0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    1.1597   -0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1072   -1.2929    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -0.8952   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005   -2.2546   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -1.2737   -2.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177    2.1655    2.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 15 31  1  0
M  END


  Mrv1652302042017092D          

 15 14  0  0  0  0            999 V2000
10001.455810000.3998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.740110000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.024410000.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.308810000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594110000.3998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.879510000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.164910000.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.879510001.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4558 9999.5736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.1694 9999.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8850 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1694 9998.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.169410000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.885010000.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.169410001.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  1  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240345

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NCCC[C@H](NC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O4/c1-6(12)10-5-3-4-8(9(14)15)11-7(2)13/h8H,3-5H2,1-2H3,(H,10,12)(H,11,13)(H,14,15)/t8-/m0/s1

> <INCHI_KEY>
XUYANFPPYJSBPU-QMMMGPOBSA-N

> <FORMULA>
C9H16N2O4

> <MOLECULAR_WEIGHT>
216.237

> <EXACT_MASS>
216.111007003

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.178356289447308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2,5-diacetamidopentanoic acid

> <ALOGPS_LOGP>
-1.11

> <JCHEM_LOGP>
-1.5174874619999998

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.40008064482269

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9385658810376643

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2660089511540131

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
52.09610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,5-diacetamidopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240345
     RDKit          3D
N2,N5-Diacetylornithine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -5.5657    0.2901    0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -0.3986    0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2849   -1.6244    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.3227    0.5432 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8541   -0.3875    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    0.5358    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -0.3505    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    0.4210    0.0205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9051   -0.5264   -0.2606 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -0.3446   -1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -1.2407   -1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3964    0.6120   -2.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    1.1053    1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822    0.7716    1.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.0914    1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0336    0.5725   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2754   -0.3363    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4503    1.2353    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763    1.3425    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -1.1712    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.8609   -0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431    1.3575   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    0.9637    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -0.8266   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -1.1623    0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    1.1597   -0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1072   -1.2929    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -0.8952   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005   -2.2546   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -1.2737   -2.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177    2.1655    2.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 04-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-20         0                                  
HETATM    1  C   UNK     0    8669.3848667.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.0488668.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.7128667.413   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.3768668.179   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8664.0428667.413   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7088668.179   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8661.3748667.413   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8662.7088669.719   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8669.3848665.871   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8670.7168665.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.0528665.871   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8670.7168663.558   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8670.7168668.179   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8672.0528667.413   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8670.7168669.719   0.000  0.00  0.00           O+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0240345
HETATM    1  C1  UNL     1      -5.566   0.290   0.795  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.285  -0.399   0.544  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.285  -1.624   0.335  1.00  0.00           O  
HETATM    4  N1  UNL     1      -3.082   0.323   0.543  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.854  -0.388   0.295  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.641   0.536   0.327  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.541  -0.350   0.054  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.810   0.421   0.020  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.905  -0.526  -0.261  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.652  -0.345  -1.435  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.778  -1.241  -1.817  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.396   0.612  -2.243  1.00  0.00           O  
HETATM   13  C9  UNL     1       2.066   1.105   1.294  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.082   0.772   1.967  1.00  0.00           O  
HETATM   15  O4  UNL     1       1.272   2.091   1.804  1.00  0.00           O  
HETATM   16  H1  UNL     1      -6.034   0.573  -0.178  1.00  0.00           H  
HETATM   17  H2  UNL     1      -6.275  -0.336   1.385  1.00  0.00           H  
HETATM   18  H3  UNL     1      -5.450   1.235   1.363  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.076   1.342   0.717  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.670  -1.171   1.057  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.862  -0.861  -0.694  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.743   1.357  -0.388  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.603   0.964   1.370  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.339  -0.827  -0.944  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.550  -1.162   0.827  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.753   1.160  -0.790  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.107  -1.293   0.390  1.00  0.00           H  
HETATM   28  H13 UNL     1       5.696  -0.895  -1.294  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.500  -2.255  -1.460  1.00  0.00           H  
HETATM   30  H15 UNL     1       4.862  -1.274  -2.906  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.118   2.166   2.804  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   13   26
CONECT    9   10   27
CONECT   10   11   12   12
CONECT   11   28   29   30
CONECT   13   14   14   15
CONECT   15   31
END

HMDB0240345
     RDKit          3D
N2,N5-Diacetylornithine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -5.5657    0.2901    0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -0.3986    0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2849   -1.6244    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.3227    0.5432 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8541   -0.3875    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    0.5358    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -0.3505    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    0.4210    0.0205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9051   -0.5264   -0.2606 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -0.3446   -1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -1.2407   -1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3964    0.6120   -2.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    1.1053    1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822    0.7716    1.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.0914    1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0336    0.5725   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2754   -0.3363    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4503    1.2353    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763    1.3425    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -1.1712    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.8609   -0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431    1.3575   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    0.9637    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -0.8266   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -1.1623    0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    1.1597   -0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1072   -1.2929    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -0.8952   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005   -2.2546   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -1.2737   -2.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177    2.1655    2.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Bisorcico	ChEBI
Bisorcicum	ChEBI
N(2),N(5)-Diacetylornithine	ChEBI
Bisorcic	HMDB
N2,N5-Diacetyl-L-ornithine	HMDB
N2,N5-Diacetylornithine	HMDB

Chemical Formula

C₉H₁₆N₂O₄

Average Molecular Weight

216.237

Monoisotopic Molecular Weight

216.111007003

IUPAC Name

(2S)-2,5-diacetamidopentanoic acid

Traditional Name

(2S)-2,5-diacetamidopentanoic acid

CAS Registry Number

39825-23-5

SMILES

CC(=O)NCCC[C@H](NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C9H16N2O4/c1-6(12)10-5-3-4-8(9(14)15)11-7(2)13/h8H,3-5H2,1-2H3,(H,10,12)(H,11,13)(H,14,15)/t8-/m0/s1

InChI Key

XUYANFPPYJSBPU-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31477923)

Excreta

Biofluid or Excreta

Feces (PMID: 29808030)

Source

Exogenous

Exogenous (HMDB: HMDB0240345)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	52.1 m³·mol⁻¹	ChemAxon
Polarizability	22.18 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	143.86	30932474
DeepCCS	[M-H]-	141.503	30932474
DeepCCS	[M-2H]-	176.765	30932474
DeepCCS	[M+Na]+	152.115	30932474
AllCCS	[M+H]+	149.1	32859911
AllCCS	[M+H-H2O]+	145.6	32859911
AllCCS	[M+NH4]+	152.3	32859911
AllCCS	[M+Na]+	153.2	32859911
AllCCS	[M-H]-	148.4	32859911
AllCCS	[M+Na-2H]-	149.4	32859911
AllCCS	[M+HCOO]-	150.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	2.78 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4769 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.85 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1023.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	227.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	229.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	281.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	357.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	611.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	177.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	957.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	463.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	237.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	212.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N2,N5-Diacetylornithine	CC(=O)NCCC[C@H](NC(C)=O)C(O)=O	3077.3	Standard polar	33892256
N2,N5-Diacetylornithine	CC(=O)NCCC[C@H](NC(C)=O)C(O)=O	2018.8	Standard non polar	33892256
N2,N5-Diacetylornithine	CC(=O)NCCC[C@H](NC(C)=O)C(O)=O	2080.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N2,N5-Diacetylornithine,1TMS,isomer #1	CC(=O)NCCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C	1938.9	Semi standard non polar	33892256
N2,N5-Diacetylornithine,1TMS,isomer #2	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O	1991.1	Semi standard non polar	33892256
N2,N5-Diacetylornithine,1TMS,isomer #3	CC(=O)NCCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C	1937.3	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #1	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1998.8	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #1	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1990.6	Standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #1	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2557.9	Standard polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #2	CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	1968.6	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #2	CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	1987.5	Standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #2	CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	2467.0	Standard polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #3	CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	1933.1	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #3	CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2041.1	Standard non polar	33892256
N2,N5-Diacetylornithine,2TMS,isomer #3	CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2530.7	Standard polar	33892256
N2,N5-Diacetylornithine,3TMS,isomer #1	CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	1954.8	Semi standard non polar	33892256
N2,N5-Diacetylornithine,3TMS,isomer #1	CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2046.9	Standard non polar	33892256
N2,N5-Diacetylornithine,3TMS,isomer #1	CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2205.0	Standard polar	33892256
N2,N5-Diacetylornithine,1TBDMS,isomer #1	CC(=O)NCCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C	2203.0	Semi standard non polar	33892256
N2,N5-Diacetylornithine,1TBDMS,isomer #2	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O	2217.1	Semi standard non polar	33892256
N2,N5-Diacetylornithine,1TBDMS,isomer #3	CC(=O)NCCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C	2193.6	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #1	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2467.4	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #1	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2407.2	Standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #1	CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2657.7	Standard polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #2	CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	2452.3	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #2	CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	2417.1	Standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #2	CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	2602.7	Standard polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #3	CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2442.9	Semi standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #3	CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2434.2	Standard non polar	33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #3	CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2657.4	Standard polar	33892256
N2,N5-Diacetylornithine,3TBDMS,isomer #1	CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2661.6	Semi standard non polar	33892256
N2,N5-Diacetylornithine,3TBDMS,isomer #1	CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2645.2	Standard non polar	33892256
N2,N5-Diacetylornithine,3TBDMS,isomer #1	CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2590.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N2,N5-Diacetylornithine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 10V, Negative-QTOF	splash10-014i-1290000000-6e78e276c45a4713d277	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 20V, Negative-QTOF	splash10-0aw9-7930000000-de76aed8b20891e48b6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 40V, Negative-QTOF	splash10-052f-9000000000-ecdf9cccc78334373356	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 10V, Positive-QTOF	splash10-014i-0890000000-054190e18f43372686ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 20V, Positive-QTOF	splash10-0900-2900000000-fa754e72201047cf4edc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 40V, Positive-QTOF	splash10-03di-9400000000-31a611ad836e3304367b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31477923	details
Blood	Detected but not Quantified	Not Quantified	Adult (40 years old)	Both	Normal	26317986	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Elderly (>65 years old)	Male	Renal failure with dialysis	26317986	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59375

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65977

PDB ID

Not Available

ChEBI ID

133217

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]

Showing metabocard for N2,N5-Diacetylornithine (HMDB0240345)

MOL for HMDB0240345 (N2,N5-Diacetylornithine)

3D MOL for HMDB0240345 (N2,N5-Diacetylornithine)

3D SDF for HMDB0240345 (N2,N5-Diacetylornithine)

3D-SDF for HMDB0240345 (N2,N5-Diacetylornithine)

PDB for HMDB0240345 (N2,N5-Diacetylornithine)

3D PDB for HMDB0240345 (N2,N5-Diacetylornithine)

SMILES for HMDB0240345 (N2,N5-Diacetylornithine)

INCHI for HMDB0240345 (N2,N5-Diacetylornithine)

Structure for HMDB0240345 (N2,N5-Diacetylornithine)

3D Structure for HMDB0240345 (N2,N5-Diacetylornithine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra