NP-MRD: Showing NP-Card for TMC-205 (NP0003883)

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Record Information

Version

2.0

Created at

2020-12-09 01:26:16 UTC

Updated at

2021-07-15 16:47:38 UTC

NP-MRD ID

NP0003883

Secondary Accession Numbers

None

Natural Product Identification

Common Name

TMC-205

Provided By

NPAtlas

Description

6-[(1E)-3-methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylic acid belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. TMC-205 is found in bacterium and Strain TC 1630. TMC-205 was first documented in 2001 (PMID: 11592499). Based on a literature review very few articles have been published on 6-[(1E)-3-methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117503D          

 30 31  0  0  0  0            999 V2000
    0.5409    0.1891   -4.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    0.0568   -3.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.0984   -4.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731    0.0715   -2.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852   -0.0549   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.0417   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -0.1933    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1865    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -0.0300    2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    0.0193    3.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.1010    4.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -0.2637    5.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0331    5.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563    0.1965    3.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.2541    1.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.1221    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    0.1101    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9644    0.1906   -5.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3031   -4.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912   -1.1685   -4.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077    0.2020   -3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    0.4625   -4.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.1922   -2.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.1754   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.3170    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921   -0.3037    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.2898    5.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    0.2744    3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5408    0.3845    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    0.2283   -0.8007 H   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  6  1  0  0  0  0
 16  9  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 26  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 17 30  1  0  0  0  0
M  END

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    0.5409    0.1891   -4.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    0.0568   -3.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.0984   -4.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731    0.0715   -2.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852   -0.0549   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.0417   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -0.1933    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1865    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -0.0300    2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    0.0193    3.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.1010    4.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -0.2637    5.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0331    5.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563    0.1965    3.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.2541    1.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.1221    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    0.1101    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9644    0.1906   -5.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3031   -4.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912   -1.1685   -4.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077    0.2020   -3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    0.4625   -4.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.1922   -2.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.1754   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.3170    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921   -0.3037    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.2898    5.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    0.2744    3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5408    0.3845    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    0.2283   -0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17  6  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END


  Mrv1652306242117503D          

 30 31  0  0  0  0            999 V2000
    0.5409    0.1891   -4.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    0.0568   -3.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.0984   -4.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731    0.0715   -2.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852   -0.0549   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.0417   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -0.1933    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1865    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -0.0300    2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    0.0193    3.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.1010    4.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -0.2637    5.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0331    5.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563    0.1965    3.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.2541    1.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.1221    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    0.1101    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9644    0.1906   -5.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3031   -4.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912   -1.1685   -4.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077    0.2020   -3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    0.4625   -4.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.1922   -2.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.1754   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.3170    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921   -0.3037    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.2898    5.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    0.2744    3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5408    0.3845    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    0.2283   -0.8007 H   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  6  1  0  0  0  0
 16  9  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 26  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 17 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003883

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H13NO2/c1-9(2)3-4-10-5-6-11-12(14(16)17)8-15-13(11)7-10/h3-8,15H,1H2,2H3,(H,16,17)/b4-3+

> <INCHI_KEY>
DGRQZYNJXNNHBY-ONEGZZNKSA-N

> <FORMULA>
C14H13NO2

> <MOLECULAR_WEIGHT>
227.263

> <EXACT_MASS>
227.094628663

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.390863956262493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E)-3-methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylic acid

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.2368697299999996

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.78993904557829

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5206239830496475

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
68.6876

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E)-3-methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    0.5409    0.1891   -4.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    0.0568   -3.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.0984   -4.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731    0.0715   -2.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852   -0.0549   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.0417   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -0.1933    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1865    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -0.0300    2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    0.0193    3.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.1010    4.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -0.2637    5.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0331    5.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563    0.1965    3.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.2541    1.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.1221    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    0.1101    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9644    0.1906   -5.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3031   -4.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912   -1.1685   -4.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077    0.2020   -3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    0.4625   -4.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.1922   -2.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.1754   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.3170    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921   -0.3037    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.2898    5.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    0.2744    3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5408    0.3845    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    0.2283   -0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17  6  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  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       0.541   0.189  -4.977  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.243   0.057  -3.869  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.712  -0.098  -4.036  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.573   0.072  -2.597  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.185  -0.055  -1.432  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.523  -0.042  -0.139  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.333  -0.193   0.991  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.764  -0.187   2.252  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.602  -0.030   2.388  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.455   0.019   3.497  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.008  -0.101   4.875  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.205  -0.264   5.145  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.946  -0.033   5.892  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.756   0.197   3.063  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.703   0.254   1.728  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.433   0.122   1.298  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.828   0.110   0.057  0.00  0.00           C+0
HETATM   18  H   UNK     0       0.964   0.191  -5.967  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.525   0.303  -4.895  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.891  -1.169  -4.283  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.308   0.202  -3.179  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.034   0.463  -4.950  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.499   0.192  -2.560  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.262  -0.175  -1.489  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.403  -0.317   0.904  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.392  -0.304   3.124  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.919  -0.290   5.763  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.653   0.274   3.694  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.541   0.385   1.112  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.467   0.228  -0.801  0.00  0.00           H+0
CONECT    1    2   18   19                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   20   21   22                                             
CONECT    4    2    5   23                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   27                                                       
CONECT   14   10   15   28                                                  
CONECT   15   14   16   29                                                  
CONECT   16   15   17    9                                                  
CONECT   17   16    6   30                                                  
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   17                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

RDKit          3D

30 31  0  0  0  0  0  0  0  0999 V2000
    0.5409    0.1891   -4.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    0.0568   -3.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.0984   -4.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731    0.0715   -2.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852   -0.0549   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.0417   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -0.1933    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1865    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -0.0300    2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    0.0193    3.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.1010    4.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -0.2637    5.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0331    5.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563    0.1965    3.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029    0.2541    1.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.1221    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    0.1101    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9644    0.1906   -5.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3031   -4.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912   -1.1685   -4.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077    0.2020   -3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    0.4625   -4.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    0.1922   -2.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.1754   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.3170    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921   -0.3037    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.2898    5.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    0.2744    3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5408    0.3845    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    0.2283   -0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17  6  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-[(1E)-3-Methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylate	Generator
(e)-6-(3-Methyl-1,3-butadienyl)- H-indole-3-carboxylic acid	MeSH

Chemical Formula

C₁₄H₁₃NO₂

Average Mass

227.2630 Da

Monoisotopic Mass

227.09463 Da

IUPAC Name

6-[(1E)-3-methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylic acid

Traditional Name

6-[(1E)-3-methylbuta-1,3-dien-1-yl]-1H-indole-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)\C=C\C1=CC2=C(C=C1)C(=CN2)C(O)=O

InChI Identifier

InChI=1S/C14H13NO2/c1-9(2)3-4-10-5-6-11-12(14(16)17)8-15-13(11)7-10/h3-8,15H,1H2,2H3,(H,16,17)/b4-3+

InChI Key

DGRQZYNJXNNHBY-ONEGZZNKSA-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
Bacterium; sewage; soil	NPAtlas	11592499
Strain TC 1630	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Indole
Pyrrole-3-carboxylic acid
Pyrrole-3-carboxylic acid or derivatives
Styrene
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous amide
Carboxylic acid derivative
Azacycle
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.19	ALOGPS
logP	3.24	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.69 m³·mol⁻¹	ChemAxon
Polarizability	25.39 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

NPA017297

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015964

Chemspider ID

7970315

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9794548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sakurai M, Kohno J, Nishio M, Yamamoto K, Okuda T, Kawano K, Nakanishi N: TMC-205 a new transcriptional up-regulator of SV40 promoter produced by an unidentified fungus. Fermentation, isolation, physico-chemical properties, structural determination and biological activities. J Antibiot (Tokyo). 2001 Aug;54(8):628-34. doi: 10.7164/antibiotics.54.628. [PubMed:11592499 ]

Showing NP-Card for TMC-205 (NP0003883)

MOL for NP0003883 (TMC-205)

3D MOL for NP0003883 (TMC-205)

3D SDF for NP0003883 (TMC-205)

3D-SDF for NP0003883 (TMC-205)

PDB for NP0003883 (TMC-205)

3D PDB for NP0003883 (TMC-205)

SMILES for NP0003883 (TMC-205)

INCHI for NP0003883 (TMC-205)

Structure for NP0003883 (TMC-205)

3D Structure for NP0003883 (TMC-205)