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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-05-18 14:04:03 UTC

Update Date

2021-09-14 15:46:14 UTC

HMDB ID

HMDB0013713

Secondary Accession Numbers

HMDB13713

Metabolite Identification

Common Name

N-Acetyltryptophan

Description

N-Acetyl-L-tryptophan or N-Acetyltryptophan, 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-Acetyltryptophan can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyltryptophan is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-tryptophan. 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‚Äôs (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-acetyltryptophan 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 tryptophan can also occur. Many N-acetylamino acids, including N-acetyltryptophan 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 ). N-Acetyltryptophan has also been used as a protein stabilizer. It prevents protein molecules from oxidative degradation by scavenging oxygen dissolved in protein solutions (PMID: 21903216 ). N-Acetyltryptophan has been identified as a catabolite of tryptophan generated by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 28916042 ). N-Acetyltryptophan is an inhibitor of cytochrome c release and an antagonist of the neurokinin 1 receptor (NK-1R). These inhibitory effects are thought have a useful role in neuroprotection. For instance, in mouse models of amyotrophic lateral sclerosis (ALS) the administration of N-Acetyltryptophan has been shown delay disease onset, extend survival, and ameliorate deterioration in motor performance ALS transgenic mice (PMID: 25986728 ). N-acetyltryptophan has been shown to significantly reduce blood-brain barrier permeability and improve functional outcome in rat models of traumatic brain injury (PMID: 29256408 ). N-Acetyltryptophan has also been shown to have a role in preventing hepatic ischemia-reperfusion injury. This is thought to occur through de-activation of the RIP2/caspase/IL-1beta signaling pathway (PMID: 31184936 ).

Structure

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

HMDB0013713
     RDKit          3D
N-Acetyltryptophan
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.1417    0.6109    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -0.1951    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698   -1.4232    0.8167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    0.4154    0.1395 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320   -0.3341    0.0587 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5504    0.2832    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -0.2251    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999   -1.1713    2.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082   -1.3410    1.8847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016   -0.5473    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141   -0.3409    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    0.5625   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926    1.2652   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    1.0535   -0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    0.1503    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -0.3292   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114    0.3449   -2.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1113   -1.0338   -1.8064 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    1.5490    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    0.8792   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    0.0581    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576    1.4139   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -1.3990    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    1.3930    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.1239    2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -1.6535    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758   -1.9951    2.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0910   -0.8887    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251    0.7309   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    2.0032   -1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    1.6166   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0308   -1.5766   -2.6472 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  1
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
M  END


  Mrv1652304062013012D          

 18 19  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0469 9999.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3325 9998.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.617910000.1439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.332410000.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.332310001.3814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.046910000.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  2  0  0  0  0
 12 14  2  0  0  0  0
 11 15  1  6  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013713

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1

> <INCHI_KEY>
DZTHIGRZJZPRDV-LBPRGKRZSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.2619

> <EXACT_MASS>
246.100442324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.251704860114437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.8148277759999996

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.258324721897573

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.170412374563318

> <JCHEM_PKA_STRONGEST_BASIC>
1.5194234386666143

> <JCHEM_POLAR_SURFACE_AREA>
85.67999999999999

> <JCHEM_REFRACTIVITY>
66.16830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013713
     RDKit          3D
N-Acetyltryptophan
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.1417    0.6109    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -0.1951    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698   -1.4232    0.8167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    0.4154    0.1395 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320   -0.3341    0.0587 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5504    0.2832    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -0.2251    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999   -1.1713    2.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082   -1.3410    1.8847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016   -0.5473    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141   -0.3409    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    0.5625   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926    1.2652   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    1.0535   -0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    0.1503    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -0.3292   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114    0.3449   -2.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1113   -1.0338   -1.8064 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    1.5490    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    0.8792   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    0.0581    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576    1.4139   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -1.3990    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    1.3930    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.1239    2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -1.6535    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758   -1.9951    2.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0910   -0.8887    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251    0.7309   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    2.0032   -1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    1.6166   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0308   -1.5766   -2.6472 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  1
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.1548664.625   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8670.4888665.395   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8669.1548663.085   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0    8667.8208666.935   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    8669.1548667.705   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8669.1548669.245   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8670.4888666.935   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   18   17   15                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0013713
HETATM    1  C1  UNL     1       5.142   0.611   0.585  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.898  -0.195   0.521  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.970  -1.423   0.817  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.691   0.415   0.140  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.432  -0.334   0.059  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.550   0.283   1.078  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.800  -0.225   1.238  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.300  -1.171   2.123  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.608  -1.341   1.885  1.00  0.00           N  
HETATM   10  C7  UNL     1      -3.002  -0.547   0.880  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.214  -0.341   0.276  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.381   0.563  -0.756  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.293   1.265  -1.177  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.085   1.054  -0.570  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.883   0.150   0.471  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.986  -0.329  -1.327  1.00  0.00           C  
HETATM   17  O2  UNL     1       1.611   0.345  -2.191  1.00  0.00           O  
HETATM   18  O3  UNL     1      -0.111  -1.034  -1.806  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.929   1.549   1.167  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.491   0.879  -0.429  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.928   0.058   1.098  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.658   1.414  -0.095  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.666  -1.399   0.359  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.537   1.393   0.959  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.068   0.124   2.074  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.698  -1.653   2.853  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.276  -1.995   2.390  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.091  -0.889   0.595  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.325   0.731  -1.234  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.316   2.003  -1.983  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.205   1.617  -0.905  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.031  -1.577  -2.647  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5   22
CONECT    5    6   16   23
CONECT    6    7   24   25
CONECT    7    8    8   15
CONECT    8    9   26
CONECT    9   10   27
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   16   17   17   18
CONECT   18   32
END

HMDB0013713
     RDKit          3D
N-Acetyltryptophan
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.1417    0.6109    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -0.1951    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698   -1.4232    0.8167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    0.4154    0.1395 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320   -0.3341    0.0587 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5504    0.2832    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -0.2251    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999   -1.1713    2.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082   -1.3410    1.8847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016   -0.5473    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141   -0.3409    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    0.5625   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926    1.2652   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    1.0535   -0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    0.1503    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -0.3292   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114    0.3449   -2.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1113   -1.0338   -1.8064 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    1.5490    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    0.8792   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    0.0581    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576    1.4139   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -1.3990    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    1.3930    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.1239    2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -1.6535    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758   -1.9951    2.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0910   -0.8887    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251    0.7309   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    2.0032   -1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    1.6166   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0308   -1.5766   -2.6472 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  1
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-N-Acetyltryptophan	HMDB
Ac-Trp	HMDB
Acetyl-L-Trp	HMDB
Acetyl-L-tryptophan	HMDB
Acetyltryptophan	HMDB
N-Acetyl-L-tryptophan	HMDB
Tryptophan, acetyl	HMDB
N-Acetyltryptophan	MeSH
(2S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acid	HMDB
(2S)-2-Acetamido-3-(1H-indol-3-yl)propionic acid	HMDB
L-N-Acetyltryptophan	HMDB
NAT	HMDB

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Weight

246.2619

Monoisotopic Molecular Weight

246.100442324

IUPAC Name

(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

1218-34-4

SMILES

CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1

InChI Key

DZTHIGRZJZPRDV-LBPRGKRZSA-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
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Acetamide
Heteroaromatic compound
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:74640 )
L-tryptophan derivative (CHEBI:74640 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	152.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002162

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.17 m³·mol⁻¹	ChemAxon
Polarizability	25.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	158.396	31661259
DarkChem	[M-H]-	157.11	31661259
DeepCCS	[M+H]+	155.769	30932474
DeepCCS	[M-H]-	153.374	30932474
DeepCCS	[M-2H]-	186.389	30932474
DeepCCS	[M+Na]+	161.72	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	157.8	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.92 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7384 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	65.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1607.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	271.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	113.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	305.7 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	327.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	776.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.7 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	1184.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	354.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	173.5 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	132.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyltryptophan	CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O	3790.7	Standard polar	33892256
N-Acetyltryptophan	CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O	2274.3	Standard non polar	33892256
N-Acetyltryptophan	CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O	2437.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyltryptophan,1TMS,isomer #1	CC(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2412.9	Semi standard non polar	33892256
N-Acetyltryptophan,1TMS,isomer #2	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2433.6	Semi standard non polar	33892256
N-Acetyltryptophan,1TMS,isomer #3	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2462.1	Semi standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #1	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2417.6	Semi standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #1	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2382.1	Standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #1	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2858.8	Standard polar	33892256
N-Acetyltryptophan,2TMS,isomer #2	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2430.4	Semi standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #2	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2358.6	Standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #2	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2892.9	Standard polar	33892256
N-Acetyltryptophan,2TMS,isomer #3	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2412.2	Semi standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #3	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2429.4	Standard non polar	33892256
N-Acetyltryptophan,2TMS,isomer #3	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2937.4	Standard polar	33892256
N-Acetyltryptophan,3TMS,isomer #1	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2446.2	Semi standard non polar	33892256
N-Acetyltryptophan,3TMS,isomer #1	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2439.7	Standard non polar	33892256
N-Acetyltryptophan,3TMS,isomer #1	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2673.5	Standard polar	33892256
N-Acetyltryptophan,1TBDMS,isomer #1	CC(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2678.1	Semi standard non polar	33892256
N-Acetyltryptophan,1TBDMS,isomer #2	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2691.8	Semi standard non polar	33892256
N-Acetyltryptophan,1TBDMS,isomer #3	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	2692.4	Semi standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #1	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2912.5	Semi standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #1	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2838.9	Standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #1	CC(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3035.5	Standard polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #2	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2887.1	Semi standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #2	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2786.0	Standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #2	CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3045.2	Standard polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #3	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2876.7	Semi standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #3	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2846.5	Standard non polar	33892256
N-Acetyltryptophan,2TBDMS,isomer #3	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3077.8	Standard polar	33892256
N-Acetyltryptophan,3TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3037.5	Semi standard non polar	33892256
N-Acetyltryptophan,3TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3052.2	Standard non polar	33892256
N-Acetyltryptophan,3TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2967.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyltryptophan GC-MS (3 TMS)	splash10-0udi-0390000000-bf959d5e1aab8cd794f3	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyltryptophan GC-MS (2 TMS)	splash10-0udi-1490000000-855cbd5624936bf3e2a1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyltryptophan GC-MS (Non-derivatized)	splash10-0udi-0390000000-bf959d5e1aab8cd794f3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyltryptophan GC-MS (Non-derivatized)	splash10-0udi-1490000000-855cbd5624936bf3e2a1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyltryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9550000000-f9186fd00d73708a5b17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyltryptophan GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9134000000-6e66aca41e26bf891fac	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyltryptophan 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 30V, Positive-QTOF	splash10-05o4-0900000000-281ce0ad760f7fc94b1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 40V, Positive-QTOF	splash10-0159-0900000000-ce991768eab82fbdbf84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 40V, Negative-QTOF	splash10-0603-9300000000-d07cb4937723d06edd48	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 30V, Negative-QTOF	splash10-0600-9300000000-2c409c01a91d64e800d7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Negative-QTOF	splash10-0f6t-3190000000-1203a50dbf1ce05d0ee5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 20V, Negative-QTOF	splash10-00di-9320000000-37f28cef4c5fd836b4f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Positive-QTOF	splash10-0pc9-0910000000-01c22859bbaf5182beff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 0V, Positive-QTOF	splash10-0002-0790000000-5c560e793d549bcec815	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 30V, Positive-QTOF	splash10-00l6-3900000000-9fecaf5dedd815d7ac9b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 0V, Positive-QTOF	splash10-0002-0690000000-87ef1c3dfb4287e7ad08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 20V, Positive-QTOF	splash10-0a4s-0900000000-e88cf6e618c54b9a2d65	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Positive-QTOF	splash10-0k9i-0940000000-5ab9f2966f1604b51cb3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Positive-QTOF	splash10-0pc9-0920000000-204470b43912cb6712bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyltryptophan 30V, Positive-QTOF	splash10-00lu-0900000000-b1fa15ca34966d5c3ebc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Positive-QTOF	splash10-0f6t-0390000000-bee3f00676dbb20cddc3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 20V, Positive-QTOF	splash10-0pb9-0960000000-ffc38c580062532632f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 40V, Positive-QTOF	splash10-001i-0900000000-5e314622f2cf80867542	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Negative-QTOF	splash10-0002-1290000000-2f09bb4277a17573a1d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 20V, Negative-QTOF	splash10-0zfs-6890000000-cf484d59c551e83dba23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 40V, Negative-QTOF	splash10-05mo-9500000000-49f44fec5a91f601a9b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Negative-QTOF	splash10-0fr2-2790000000-64600864aeea894a8f16	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 20V, Negative-QTOF	splash10-01b9-9600000000-fee48c2c347edd3e362e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 40V, Negative-QTOF	splash10-014l-7900000000-baeeeec89ae0148886b5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 10V, Positive-QTOF	splash10-054t-0390000000-e119f5a3710d3fba6328	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyltryptophan 20V, Positive-QTOF	splash10-0a4u-0910000000-7fc91bffadf6c81532dc	2021-09-24	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	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Male	Normal	18439883	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	1.291 umol/mmol creatinine	Adult (>18 years old)	Female	Pregnancy	28916042	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

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 ]
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 ]
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 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

700653

PDB ID

Not Available

ChEBI ID

74640

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

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 ]
Fang L, Parti R, Hu P: Characterization of N-acetyltryptophan degradation products in concentrated human serum albumin solutions and development of an automated high performance liquid chromatography-mass spectrometry method for their quantitation. J Chromatogr A. 2011 Oct 14;1218(41):7316-24. doi: 10.1016/j.chroma.2011.08.044. Epub 2011 Aug 18. [PubMed:21903216 ]
Pavlova T, Vidova V, Bienertova-Vasku J, Janku P, Almasi M, Klanova J, Spacil Z: Urinary intermediates of tryptophan as indicators of the gut microbial metabolism. Anal Chim Acta. 2017 Sep 22;987:72-80. doi: 10.1016/j.aca.2017.08.022. Epub 2017 Aug 26. [PubMed:28916042 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Li W, Fotinos A, Wu Q, Chen Y, Zhu Y, Baranov S, Tu Y, Zhou EW, Sinha B, Kristal BS, Wang X: N-acetyl-L-tryptophan delays disease onset and extends survival in an amyotrophic lateral sclerosis transgenic mouse model. Neurobiol Dis. 2015 Aug;80:93-103. doi: 10.1016/j.nbd.2015.05.002. Epub 2015 May 16. [PubMed:25986728 ]
Ameliorate JL, Ghabriel MN, Vink R: Magnesium enhances the beneficial effects of NK1 antagonist administration on blood-brain barrier permeability and motor outcome after traumatic brain injury. Magnes Res. 2017 Aug 1;30(3):88-97. doi: 10.1684/mrh.2017.0427. [PubMed:29256408 ]
Wang J, Yu S, Li J, Li H, Jiang H, Xiao P, Pan Y, Zheng J, Yu L, Jiang J: Protective role of N-acetyl-l-tryptophan against hepatic ischemia-reperfusion injury via the RIP2/caspase-1/IL-1beta signaling pathway. Pharm Biol. 2019 Dec;57(1):385-391. doi: 10.1080/13880209.2019.1617750. [PubMed:31184936 ]

Showing metabocard for N-Acetyltryptophan (HMDB0013713)

MOL for HMDB0013713 (N-Acetyltryptophan)

3D MOL for HMDB0013713 (N-Acetyltryptophan)

3D SDF for HMDB0013713 (N-Acetyltryptophan)

3D-SDF for HMDB0013713 (N-Acetyltryptophan)

PDB for HMDB0013713 (N-Acetyltryptophan)

3D PDB for HMDB0013713 (N-Acetyltryptophan)

SMILES for HMDB0013713 (N-Acetyltryptophan)

INCHI for HMDB0013713 (N-Acetyltryptophan)

Structure for HMDB0013713 (N-Acetyltryptophan)

3D Structure for HMDB0013713 (N-Acetyltryptophan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra