NP-MRD: Showing NP-Card for N-Acetyltryptophan (NP0004446)

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Record Information

Version

2.0

Created at

2020-12-09 01:54:33 UTC

Updated at

2021-08-19 23:59:35 UTC

NP-MRD ID

NP0004446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyltryptophan

Provided By

NPAtlas

Description

N-Acetyl-D-tryptophan 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-Acetyl-D-tryptophan is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. N-Acetyltryptophan is found in Arabidopsis thaliana, Bacillus and Salsola collina. N-Acetyltryptophan was first documented in 2004 (PMID: 15046641). Based on a literature review a small amount of articles have been published on N-Acetyl-D-tryptophan (PMID: 34310940) (PMID: 33713012) (PMID: 30280329) (PMID: 27987726) (PMID: 27748798) (PMID: 26031348).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118063D          

 32 33  0  0  0  0            999 V2000
    2.9394   -2.2113    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -0.8179    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.0522    2.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9539   -0.2975   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    1.0443   -0.2263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3985    1.3508   -1.1552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8875    0.7120   -1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.6887   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462    0.0471   -1.8560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.3536   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -1.0434    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -1.3270    1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.8956    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937   -0.2086    1.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.0586   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672    1.8165   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7437    1.3001   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    3.1717   -0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -2.4316    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -2.9192    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -2.3616    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534   -0.8919   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    1.5469    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    1.1804   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    2.4664   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    1.1001   -3.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -0.1413   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -1.3602   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114   -1.8664    2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.1397    3.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    0.1031    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    3.7323   -0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  1  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 18 32  1  0  0  0  0
M  END

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    2.9394   -2.2113    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -0.8179    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.0522    2.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9539   -0.2975   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    1.0443   -0.2263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3985    1.3508   -1.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.7120   -1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.6887   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462    0.0471   -1.8560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.3536   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -1.0434    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -1.3270    1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.8956    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937   -0.2086    1.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.0586   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672    1.8165   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7437    1.3001   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    3.1717   -0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -2.4316    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -2.9192    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -2.3616    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534   -0.8919   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    1.5469    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    1.1804   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    2.4664   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    1.1001   -3.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -0.1413   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -1.3602   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114   -1.8664    2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.1397    3.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    0.1031    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    3.7323   -0.4463 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


  Mrv1652306242118063D          

 32 33  0  0  0  0            999 V2000
    2.9394   -2.2113    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -0.8179    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.0522    2.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9539   -0.2975   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    1.0443   -0.2263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3985    1.3508   -1.1552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8875    0.7120   -1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.6887   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462    0.0471   -1.8560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.3536   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -1.0434    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -1.3270    1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.8956    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937   -0.2086    1.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.0586   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672    1.8165   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7437    1.3001   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    3.1717   -0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -2.4316    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -2.9192    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -2.3616    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534   -0.8919   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    1.5469    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    1.1804   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    2.4664   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    1.1001   -3.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -0.1413   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -1.3602   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114   -1.8664    2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.1397    3.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    0.1031    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    3.7323   -0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  1  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 18 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

> <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-/m1/s1

> <INCHI_KEY>
DZTHIGRZJZPRDV-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.266

> <EXACT_MASS>
246.100442319

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.06327270353636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetamido-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
0.9952236489999997

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.3692976360967

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.118376794125576

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9831907949267458

> <JCHEM_POLAR_SURFACE_AREA>
82.19

> <JCHEM_REFRACTIVITY>
65.6466

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyltryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    2.9394   -2.2113    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -0.8179    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.0522    2.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9539   -0.2975   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    1.0443   -0.2263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3985    1.3508   -1.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.7120   -1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.6887   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462    0.0471   -1.8560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.3536   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -1.0434    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -1.3270    1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.8956    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937   -0.2086    1.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.0586   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672    1.8165   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7437    1.3001   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    3.1717   -0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -2.4316    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -2.9192    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -2.3616    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534   -0.8919   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    1.5469    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    1.1804   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    2.4664   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    1.1001   -3.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -0.1413   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -1.3602   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114   -1.8664    2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.1397    3.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    0.1031    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    3.7323   -0.4463 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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.939  -2.211   1.219  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.433  -0.818   1.069  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.425  -0.052   2.080  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.954  -0.298  -0.157  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.479   1.044  -0.226  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.399   1.351  -1.155  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.888   0.712  -1.088  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.736   0.689  -2.209  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.846   0.047  -1.856  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.783  -0.354  -0.575  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.654  -1.043   0.242  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.310  -1.327   1.552  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.066  -0.896   2.016  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.194  -0.209   1.209  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.556   0.059  -0.081  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.817  -0.801  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.744   1.300  -1.093  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.478   3.172  -0.987  0.00  0.00           O+0
HETATM   19  H   UNK     0       3.058  -2.432   2.301  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.205  -2.919   0.812  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.920  -2.362   0.719  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.953  -0.892  -0.986  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.434   1.547   0.788  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.824   1.180  -2.196  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.251   2.466  -1.145  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.565   1.100  -3.193  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.679  -0.141  -2.463  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.611  -1.360  -0.161  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.011  -1.866   2.158  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.839  -1.140   3.043  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.253   0.103   1.610  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.829   3.732  -0.446  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6   16   23                                             
CONECT    6    5    7   24   25                                             
CONECT    7    6    8   15                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14    7   10                                                  
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   32                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    6                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

RDKit          3D

32 33  0  0  0  0  0  0  0  0999 V2000
    2.9394   -2.2113    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -0.8179    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.0522    2.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9539   -0.2975   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    1.0443   -0.2263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3985    1.3508   -1.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.7120   -1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.6887   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462    0.0471   -1.8560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.3536   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -1.0434    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -1.3270    1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -0.8956    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937   -0.2086    1.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.0586   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672    1.8165   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7437    1.3001   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    3.1717   -0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -2.4316    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -2.9192    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -2.3616    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534   -0.8919   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    1.5469    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    1.1804   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    2.4664   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    1.1001   -3.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -0.1413   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -1.3602   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114   -1.8664    2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.1397    3.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    0.1031    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    3.7323   -0.4463 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 NMR Assignments

Synonyms

Value	Source
Acetyltryptophan	ChEBI
N-Acetyl-DL-tryptophan	ChEBI
N-Acetyltryptophane	ChEBI
N-Acetyltryptophan	HMDB
N-Acetyltryptophanate sodium	HMDB
N-Acetyl-D-tryptophan	MeSH

Chemical Formula

C₁₃H₁₄N₂O₃

Average Mass

246.2660 Da

Monoisotopic Mass

246.10044 Da

IUPAC Name

2-acetamido-3-(1H-indol-3-yl)propanoic acid

Traditional Name

N-acetyltryptophan

CAS Registry Number

Not Available

SMILES

CC(=O)NC(CC1=CNC2=CC=CC=C12)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)

InChI Key

DZTHIGRZJZPRDV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633
Bacillus	NPAtlas	12480104
Salsola collina	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

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-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acetyl-amino acid (CHEBI:70976 )
tryptophan derivative (CHEBI:70976 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	205.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	586.00 to 588.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1200 mg/L @ 21C (exp)	The Good Scents Company Information System
LogP	-0.408 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.45	ALOGPS
logP	1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.65 m³·mol⁻¹	ChemAxon
Polarizability	25.06 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

External Links

NPAtlas ID

NPA015473

HMDB ID

HMDB0255052

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047984

Chemspider ID

1925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2002

PDB ID

Not Available

ChEBI ID

70976

Good Scents ID

rw1265471

References

General References

Duncan KM, Steel WH, Walker RA: Amino acids change solute affinity for lipid bilayers. Biophys J. 2021 Jul 24. pii: S0006-3495(21)00607-X. doi: 10.1016/j.bpj.2021.07.021. [PubMed:34310940 ]
Doshi N, Giddings J, Luis L, Wu A, Ritchie K, Liu W, Chan W, Taing R, Chu J, Sreedhara A, Kannan A, Kei P, Shieh I, Graf T, Hu M: A Comprehensive Assessment of All-Oleate Polysorbate 80: Free Fatty Acid Particle Formation, Interfacial Protection and Oxidative Degradation. Pharm Res. 2021 Mar;38(3):531-548. doi: 10.1007/s11095-021-03021-z. Epub 2021 Mar 12. [PubMed:33713012 ]
Dion MZ, Leiske D, Sharma VK, Zuch de Zafra CL, Salisbury CM: Mitigation of Oxidation in Therapeutic Antibody Formulations: a Biochemical Efficacy and Safety Evaluation of N-Acetyl-Tryptophan and L-Methionine. Pharm Res. 2018 Oct 2;35(11):222. doi: 10.1007/s11095-018-2467-5. [PubMed:30280329 ]
Upadhyay A, Dalvi SV, Gupta G, Khanna N: Effect of PEGylation on performance of protein microbubbles and its comparison with lipid microbubbles. Mater Sci Eng C Mater Biol Appl. 2017 Feb 1;71:425-430. doi: 10.1016/j.msec.2016.10.021. Epub 2016 Oct 17. [PubMed:27987726 ]
Matos Do Canto L, Marian C, Varghese RS, Ahn J, Da Cunha PA, Willey S, Sidawy M, Rone JD, Cheema AK, Luta G, Nezami Ranjbar MR, Ressom HW, Haddad BR: Metabolomic profiling of breast tumors using ductal fluid. Int J Oncol. 2016 Dec;49(6):2245-2254. doi: 10.3892/ijo.2016.3732. Epub 2016 Oct 13. [PubMed:27748798 ]
Sirianni AC, Jiang J, Zeng J, Mao LL, Zhou S, Sugarbaker P, Zhang X, Li W, Friedlander RM, Wang X: N-acetyl-l-tryptophan, but not N-acetyl-d-tryptophan, rescues neuronal cell death in models of amyotrophic lateral sclerosis. J Neurochem. 2015 Sep;134(5):956-68. doi: 10.1111/jnc.13190. Epub 2015 Jul 14. [PubMed:26031348 ]
Reine PA, Kongsgaard UE, Andersen A, Thogersen AK, Olsen H: Infusions of albumin increase free fraction of naproxen in healthy volunteers: a randomized crossover study. Acta Anaesthesiol Scand. 2010 Apr;54(4):430-4. doi: 10.1111/j.1399-6576.2009.02142.x. Epub 2009 Oct 29. [PubMed:19878101 ]
Reine PA, Kongsgaard UE, Andersen A, Thogersen AK, Olsen H: Infusion of albumin attenuates changes in serum protein binding of drugs in surgical patients compared with volume replacement with HAES. Acta Anaesthesiol Scand. 2008 Mar;52(3):406-12. doi: 10.1111/j.1399-6576.2007.01555.x. [PubMed:18269390 ]
Olsen H, Andersen A, Nordbo A, Kongsgaard UE, Bormer OP: Pharmaceutical-grade albumin: impaired drug-binding capacity in vitro. BMC Clin Pharmacol. 2004 Mar 29;4:4. doi: 10.1186/1472-6904-4-4. [PubMed:15046641 ]

Showing NP-Card for N-Acetyltryptophan (NP0004446)

MOL for NP0004446 (N-Acetyltryptophan)

3D MOL for NP0004446 (N-Acetyltryptophan)

3D SDF for NP0004446 (N-Acetyltryptophan)

3D-SDF for NP0004446 (N-Acetyltryptophan)

PDB for NP0004446 (N-Acetyltryptophan)

3D PDB for NP0004446 (N-Acetyltryptophan)

SMILES for NP0004446 (N-Acetyltryptophan)

INCHI for NP0004446 (N-Acetyltryptophan)

Structure for NP0004446 (N-Acetyltryptophan)

3D Structure for NP0004446 (N-Acetyltryptophan)