NP-MRD: Showing NP-Card for N-(3-Indolylacetyl)-L-alanine (NP0002849)

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Record Information

Version

1.0

Created at

2020-11-23 19:41:58 UTC

Updated at

2021-08-12 19:52:19 UTC

NP-MRD ID

NP0002849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-(3-Indolylacetyl)-L-alanine

Provided By

BMRB

Description

N-(indole-3-acetyl)-L-alanine is also known as iaa-ala. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on N-(indole-3-acetyl)-L-alanine.

Structure

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


     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8393    0.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3769    0.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7105   -1.4364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -2.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -3.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1775   -2.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2558   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561   -2.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.6079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403   -0.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0095    1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7790    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    1.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433    1.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473    1.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1430    2.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3487   -1.0512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8695    1.8594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3017    0.6933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1682   -0.0978    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0792   -2.0501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -0.8182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648   -3.4475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.9713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022   -2.0926    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5093    1.0909    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481    3.7109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484    3.7554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.0275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    3.9710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  1
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  6 24  1  1
  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

NP0002849
     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    4.1858   -1.4499   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162   -0.2492    0.5946 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2428   -0.4535    0.9507 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212   -0.7867    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6004   -0.9744   -1.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -0.9761    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657   -0.0469   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6437    0.9002   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7835    1.5374   -1.4542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    1.0011   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565    1.2865   -0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052    0.5805    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5572   -0.4188    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017   -0.6958    0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    0.0062    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.9766   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.2345   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.8470   -0.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -1.3697   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474   -2.3998    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -1.4626   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034   -0.1894    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850   -1.7556   -1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244   -0.8335    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -2.0229    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    1.1309   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8484    2.3103   -2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    2.0641   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0720    0.7871    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504   -0.9429    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998   -1.4587    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264    2.8241   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  4  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
  2 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
  2 22  1  1
  5 23  1  0
  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


     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8393    0.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3769    0.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7105   -1.4364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -2.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -3.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1775   -2.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2558   -1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561   -2.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.6079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403   -0.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0095    1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7790    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    1.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433    1.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473    1.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1430    2.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3487   -1.0512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8695    1.8594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3017    0.6933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1682   -0.0978    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0792   -2.0501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -0.8182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648   -3.4475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.9713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022   -2.0926    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5093    1.0909    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481    3.7109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484    3.7554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.0275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    3.9710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  1
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  6 24  1  1
  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
> <DATABASE_ID>
NP0002849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(N=C(O)CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-8(13(17)18)15-12(16)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7-8,14H,6H2,1H3,(H,15,16)(H,17,18)/t8-/m0/s1

> <INCHI_KEY>
FBDCJLXTUCMFLF-QMMMGPOBSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.2619

> <EXACT_MASS>
246.100442324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.924254070442476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}propanoic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.9928412279999996

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.230122023747842

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.11244047800989

> <JCHEM_PKA_STRONGEST_BASIC>
1.5315922456578834

> <JCHEM_POLAR_SURFACE_AREA>
85.67999999999999

> <JCHEM_REFRACTIVITY>
66.27120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002849
     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    4.1858   -1.4499   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162   -0.2492    0.5946 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2428   -0.4535    0.9507 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212   -0.7867    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6004   -0.9744   -1.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -0.9761    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657   -0.0469   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6437    0.9002   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7835    1.5374   -1.4542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    1.0011   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565    1.2865   -0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052    0.5805    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5572   -0.4188    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017   -0.6958    0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    0.0062    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.9766   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.2345   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.8470   -0.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -1.3697   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474   -2.3998    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -1.4626   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034   -0.1894    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850   -1.7556   -1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244   -0.8335    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -2.0229    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    1.1309   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8484    2.3103   -2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    2.0641   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0720    0.7871    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504   -0.9429    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998   -1.4587    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264    2.8241   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  4  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
  2 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
  2 22  1  1
  5 23  1  0
  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                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   14                                                       
CONECT    8    1   13   15   19                                             
CONECT    9    6    7   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    5   10   14                                                  
CONECT   12    6   15   16                                                  
CONECT   13    8   17   18                                                  
CONECT   14    7   11                                                       
CONECT   15    8   12                                                       
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19    8                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    NP0002849
HETATM    1  C1  UNL     1       4.186  -1.450  -0.153  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.616  -0.249   0.595  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.243  -0.454   0.951  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.321  -0.787   0.101  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.600  -0.974  -1.243  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.064  -0.976   0.554  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.966  -0.047  -0.136  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.644   0.900  -1.085  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.784   1.537  -1.454  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.798   1.001  -0.751  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.156   1.287  -0.748  1.00  0.00           C  
HETATM   12  C9  UNL     1      -5.005   0.581   0.081  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.557  -0.419   0.926  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.202  -0.696   0.915  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.343   0.006   0.088  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.846   0.977  -0.195  1.00  0.00           C  
HETATM   17  O2  UNL     1       5.016   1.234  -0.550  1.00  0.00           O  
HETATM   18  O3  UNL     1       2.813   1.847  -0.554  1.00  0.00           O  
HETATM   19  H1  UNL     1       5.307  -1.370  -0.146  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.847  -2.400   0.307  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.886  -1.463  -1.214  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.203  -0.189   1.546  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.285  -1.756  -1.787  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.124  -0.833   1.668  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.409  -2.023   0.374  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.330   1.131  -1.494  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.848   2.310  -2.164  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.505   2.064  -1.406  1.00  0.00           H  
HETATM   29  H11 UNL     1      -6.072   0.787   0.099  1.00  0.00           H  
HETATM   30  H12 UNL     1      -5.250  -0.943   1.553  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.800  -1.459   1.549  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.026   2.824  -0.617  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   16   22
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   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

NP0002849
     RDKit          3D

32 33  0  0  0  0  0  0  0  0999 V2000
    4.1858   -1.4499   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162   -0.2492    0.5946 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2428   -0.4535    0.9507 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212   -0.7867    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6004   -0.9744   -1.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -0.9761    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657   -0.0469   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6437    0.9002   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7835    1.5374   -1.4542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    1.0011   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565    1.2865   -0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052    0.5805    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5572   -0.4188    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017   -0.6958    0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    0.0062    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.9766   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.2345   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.8470   -0.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -1.3697   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474   -2.3998    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -1.4626   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034   -0.1894    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850   -1.7556   -1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244   -0.8335    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -2.0229    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    1.1309   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8484    2.3103   -2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    2.0641   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0720    0.7871    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504   -0.9429    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998   -1.4587    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264    2.8241   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  4  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
  2 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
  2 22  1  1
  5 23  1  0
  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

Synonyms

Value	Source
IAA-ala	ChEBI
IAA-L-ala	ChEBI
N-(Indole-3-acetyl)alanine	ChEBI

Chemical Formula

C₁₃H₁₄N₂O₃

Average Mass

246.2619 Da

Monoisotopic Mass

246.10044 Da

IUPAC Name

(2S)-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}propanoic acid

Traditional Name

(2S)-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(N=C(O)CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(13(17)18)15-12(16)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7-8,14H,6H2,1H3,(H,15,16)(H,17,18)/t8-/m0/s1

InChI Key

FBDCJLXTUCMFLF-QMMMGPOBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, ethanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, ethanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, ethanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoleacetic acid amide conjugate (CHEBI:71672 )
N-acyl-L-alanine (CHEBI:71672 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.63	ALOGPS
logP	1.99	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	1.53	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	66.27 m³·mol⁻¹	ChemAxon
Polarizability	24.92 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

559246

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71672

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]

Showing NP-Card for N-(3-Indolylacetyl)-L-alanine (NP0002849)

MOL for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

3D MOL for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

3D SDF for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

3D-SDF for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

PDB for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

3D PDB for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

SMILES for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

INCHI for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

Structure for NP0002849 (N-(3-Indolylacetyl)-L-alanine)

3D Structure for NP0002849 (N-(3-Indolylacetyl)-L-alanine)