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Showing metabocard for N-Acetylproline (HMDB0094701)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2017-08-01 02:19:39 UTC
Update Date2023-05-30 20:55:51 UTC
HMDB IDHMDB0094701
Secondary Accession Numbers
  • HMDB94701
Metabolite Identification
Common NameN-Acetylproline
DescriptionN-Acetyl-L-proline or N-Acetylproline, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylproline can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylproline is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-proline. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylproline can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free proline can also occur. Many N-acetylamino acids, including N-acetylproline are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).
Structure
Data?1677000677
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0094701 (N-Acetylproline)


  Mrv0541 05041408122D          

 12 12  0  0  1  0            999 V2000
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  6  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
  6 12  1  1  0  0  0
M  END
Download

3D MOL for HMDB0094701 (N-Acetylproline)

HMDB0094701
     RDKit          3D
N-Acetylproline
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.5099   -0.7579   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971   -1.3776    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -2.5121    0.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -0.7267    0.2176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -1.2379    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.6477   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    0.7831   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.5503   -0.4203 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5628    1.6529    0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612    1.4030    1.2323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    2.9206   -0.2926 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147   -0.3749    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715    0.0392   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548   -1.5544   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543   -0.7888    1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504   -2.3388    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867   -1.0989   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209   -0.7269    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    1.2345    0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792    1.3593   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    0.5213   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    3.6788   -0.0153 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  2  0
  9 11  1  0
  8  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  6
 11 22  1  0
M  END
Download

3D SDF for HMDB0094701 (N-Acetylproline)


  Mrv0541 05041408122D          

 12 12  0  0  1  0            999 V2000
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  6  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
  6 12  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0094701

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CCCN1C(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m0/s1

> <INCHI_KEY>
GNMSLDIYJOSUSW-LURJTMIESA-N

> <FORMULA>
C7H11NO3

> <MOLECULAR_WEIGHT>
157.1671

> <EXACT_MASS>
157.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.470980940620374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-acetylpyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-0.48719913400000003

> <ALOGPS_LOGS>
0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.893524455893097

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1182616826574119

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
37.6302

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylproline

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0094701 (N-Acetylproline)

HMDB0094701
     RDKit          3D
N-Acetylproline
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.5099   -0.7579   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971   -1.3776    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -2.5121    0.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -0.7267    0.2176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -1.2379    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.6477   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    0.7831   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.5503   -0.4203 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5628    1.6529    0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612    1.4030    1.2323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    2.9206   -0.2926 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147   -0.3749    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715    0.0392   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548   -1.5544   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543   -0.7888    1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504   -2.3388    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867   -1.0989   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209   -0.7269    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    1.2345    0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792    1.3593   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    0.5213   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    3.6788   -0.0153 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  2  0
  9 11  1  0
  8  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  6
 11 22  1  0
M  END
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PDB for HMDB0094701 (N-Acetylproline)

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    8                                                       
CONECT    5    1    8    9                                                  
CONECT    6    3    7    8   12                                             
CONECT    7    6   10   11                                                  
CONECT    8    4    5    6                                                  
CONECT    9    5                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0094701 (N-Acetylproline)

COMPND    HMDB0094701
HETATM    1  C1  UNL     1       2.510  -0.758  -0.288  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.297  -1.378   0.301  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.398  -2.512   0.888  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.046  -0.727   0.218  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.196  -1.238   0.754  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.178  -0.648  -0.268  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.684   0.783  -0.314  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.176   0.550  -0.420  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.563   1.653   0.244  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.261   1.403   1.232  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.424   2.921  -0.293  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.215  -0.375   0.478  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.171   0.039  -0.976  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.055  -1.554  -0.874  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.354  -0.789   1.747  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.250  -2.339   0.740  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.987  -1.099  -1.244  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.221  -0.727   0.078  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.884   1.234   0.679  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.079   1.359  -1.151  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.037   0.521  -1.514  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.033   3.679  -0.015  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5    8
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   21
CONECT    9   10   10   11
CONECT   11   22
END
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SMILES for HMDB0094701 (N-Acetylproline)

[H][C@]1(CCCN1C(C)=O)C(O)=O
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INCHI for HMDB0094701 (N-Acetylproline)

InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-1-Acetylpyrrolidine-2-carboxylic acidChEBI
AcetylprolineChEBI
(2S)-1-Acetylpyrrolidine-2-carboxylateGenerator
Chemical FormulaC7H11NO3
Average Molecular Weight157.1671
Monoisotopic Molecular Weight157.073893223
IUPAC Name(2S)-1-acetylpyrrolidine-2-carboxylic acid
Traditional Nameacetylproline
CAS Registry Number68-95-1
SMILES
[H][C@]1(CCCN1C(C)=O)C(O)=O
InChI Identifier
InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m0/s1
InChI KeyGNMSLDIYJOSUSW-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Acetamide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organoheterocyclic compound
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available134.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00002073
Predicted Molecular Properties
PropertyValueSource
logP-0.51ALOGPS
logP-0.49ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.63 m³·mol⁻¹ChemAxon
Polarizability15.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.79531661259
DarkChem[M-H]-129.70231661259
DeepCCS[M+H]+129.10930932474
DeepCCS[M-H]-126.27530932474
DeepCCS[M-2H]-163.1130932474
DeepCCS[M+Na]+138.50730932474
AllCCS[M+H]+133.732859911
AllCCS[M+H-H2O]+129.432859911
AllCCS[M+NH4]+137.732859911
AllCCS[M+Na]+138.932859911
AllCCS[M-H]-130.632859911
AllCCS[M+Na-2H]-132.032859911
AllCCS[M+HCOO]-133.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.16 minutes32390414
Predicted by Siyang on May 30, 20229.2886 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.82 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1032.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid286.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid85.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid170.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid58.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid237.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid296.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)363.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid607.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid138.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid929.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid193.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid196.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate525.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA252.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water220.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetylproline[H][C@]1(CCCN1C(C)=O)C(O)=O2228.1Standard polar33892256
N-Acetylproline[H][C@]1(CCCN1C(C)=O)C(O)=O1421.1Standard non polar33892256
N-Acetylproline[H][C@]1(CCCN1C(C)=O)C(O)=O1582.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylproline,1TMS,isomer #1CC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C1480.7Semi standard non polar33892256
N-Acetylproline,1TBDMS,isomer #1CC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C1706.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylproline GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-9300000000-defdd568f7cdb7d565252017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylproline GC-MS (1 TMS) - 70eV, Positivesplash10-03kc-9400000000-3cd78dbab864adf302672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylproline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 10V, Positive-QTOFsplash10-0a4i-0900000000-47cdd30cd1badb23d7932017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 20V, Positive-QTOFsplash10-096r-4900000000-4f15ca0bc330bf87b5212017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 40V, Positive-QTOFsplash10-0006-9000000000-3f666f354e69b72329a52017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 10V, Negative-QTOFsplash10-0bt9-0900000000-5e1bc65351b385ba7aa92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 20V, Negative-QTOFsplash10-03di-5900000000-6e692a48a6e02ce8321d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 40V, Negative-QTOFsplash10-00r6-9100000000-f8c2687cfbf901e0c7952017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 10V, Positive-QTOFsplash10-03k9-4900000000-8dde265dd08c9524ee0f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 20V, Positive-QTOFsplash10-00di-9300000000-83c5640b4755226f6ad62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 40V, Positive-QTOFsplash10-00di-9000000000-24cc3e57adc9f9cfd85c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 10V, Negative-QTOFsplash10-03di-3900000000-c815567db247737737cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 20V, Negative-QTOFsplash10-03xs-9500000000-c91ce95925868ba568302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylproline 40V, Negative-QTOFsplash10-029g-9100000000-47f27ca4f4188b449d302021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.43 (0.25-0.60) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Associated OMIM IDs
DrugBank IDDB03360
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound66141
PDB IDN7P
ChEBI ID21560
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
  2. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
  3. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
  4. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
  5. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
  6. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]