NP-MRD: Showing NP-Card for Phomazine A (NP0012356)

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Record Information

Version

2.0

Created at

2021-01-05 21:46:00 UTC

Updated at

2021-07-15 17:11:32 UTC

NP-MRD ID

NP0012356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phomazine A

Provided By

NPAtlas

Description

(3Z,5aS,6S,10aR)-1,6-dihydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-3H,4H,5aH,6H,10H,10aH-pyrazino[1,2-a]indol-4-one belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Phomazine A is found in Phoma sp. OUCMDZ-1847. Based on a literature review very few articles have been published on (3Z,5aS,6S,10aR)-1,6-dihydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-3H,4H,5aH,6H,10H,10aH-pyrazino[1,2-a]indol-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117073D          

 43 46  0  0  0  0            999 V2000
   -1.2703    3.0897   -1.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    1.3157   -1.5788 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003    1.0331    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3355    1.6009    0.8866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2999    0.5490    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    0.4692    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1914   -0.8070   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -1.9194    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1413   -1.9493    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0465   -2.8922    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392   -0.6984    0.9404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2017   -0.3911    0.5179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.2295    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -2.4776    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -0.6095    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.3841    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.8437    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -0.0204    1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4432    0.4700    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566    0.1324    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652   -0.6933   -0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893   -1.1901   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    0.7946    0.5400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    1.5875    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.7264    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769    3.5422   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    3.3202   -2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    3.6502   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    1.5501    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.6042    0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0938    1.3737   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -0.8003   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0291   -2.8844   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -2.4298   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -3.8037    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884   -0.6494    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -2.4868    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    0.2646    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    1.1176    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    0.5310    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780   -0.9745   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374   -1.8396   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.2517    0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 12  3  1  0  0  0  0
 22 17  1  0  0  0  0
 24  3  1  0  0  0  0
 11  5  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  6  0  0  0
 10 35  1  0  0  0  0
 11 36  1  1  0  0  0
 16 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
 22 42  1  0  0  0  0
 23 43  1  0  0  0  0
M  END

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.2703    3.0897   -1.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    1.3157   -1.5788 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003    1.0331    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3355    1.6009    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2999    0.5490    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    0.4692    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1914   -0.8070   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -1.9194    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1413   -1.9493    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0465   -2.8922    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392   -0.6984    0.9404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2017   -0.3911    0.5179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.2295    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -2.4776    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -0.6095    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.3841    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.8437    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -0.0204    1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4432    0.4700    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566    0.1324    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652   -0.6933   -0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893   -1.1901   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    0.7946    0.5400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    1.5875    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.7264    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769    3.5422   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    3.3202   -2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    3.6502   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    1.5501    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.6042    0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0938    1.3737   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -0.8003   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0291   -2.8844   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -2.4298   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -3.8037    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884   -0.6494    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -2.4868    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    0.2646    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    1.1176    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    0.5310    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780   -0.9745   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374   -1.8396   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.2517    0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 24 25  2  0
 12  3  1  0
 22 17  1  0
 24  3  1  0
 11  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 11 36  1  1
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv1652306242117073D          

 43 46  0  0  0  0            999 V2000
   -1.2703    3.0897   -1.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    1.3157   -1.5788 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003    1.0331    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3355    1.6009    0.8866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2999    0.5490    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    0.4692    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1914   -0.8070   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -1.9194    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1413   -1.9493    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0465   -2.8922    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392   -0.6984    0.9404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2017   -0.3911    0.5179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.2295    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -2.4776    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -0.6095    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.3841    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.8437    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -0.0204    1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4432    0.4700    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566    0.1324    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652   -0.6933   -0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893   -1.1901   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    0.7946    0.5400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    1.5875    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.7264    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769    3.5422   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    3.3202   -2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    3.6502   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    1.5501    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.6042    0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0938    1.3737   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -0.8003   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0291   -2.8844   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -2.4298   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -3.8037    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884   -0.6494    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -2.4868    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    0.2646    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    1.1176    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    0.5310    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780   -0.9745   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374   -1.8396   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.2517    0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 12  3  1  0  0  0  0
 22 17  1  0  0  0  0
 24  3  1  0  0  0  0
 11  5  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  6  0  0  0
 10 35  1  0  0  0  0
 11 36  1  1  0  0  0
 16 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
 22 42  1  0  0  0  0
 23 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0012356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])=C([H])C([H])=C2C([H])([H])[C@]3(SC([H])([H])[H])N(C(=O)\C(N([H])C3=O)=C(/[H])C3=C([H])C([H])=C([H])C([H])=C3[H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H18N2O3S/c1-25-19-11-13-8-5-9-15(22)16(13)21(19)17(23)14(20-18(19)24)10-12-6-3-2-4-7-12/h2-10,15-16,22H,11H2,1H3,(H,20,24)/b14-10-/t15-,16-,19+/m0/s1

> <INCHI_KEY>
JDNKAJXFWBFPPM-TUGLFXRSSA-N

> <FORMULA>
C19H18N2O3S

> <MOLECULAR_WEIGHT>
354.42

> <EXACT_MASS>
354.103813622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.29045819662864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5aS,6S,10aR)-6-hydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-1H,2H,3H,4H,5aH,6H,10H,10aH-pyrazino[1,2-a]indole-1,4-dione

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.5995824060000001

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.13800900825483

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.617487243319522

> <JCHEM_PKA_STRONGEST_BASIC>
-0.335137655686364

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
100.2125

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5aS,6S,10aR)-6-hydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-2H,5aH,6H,10H-pyrazino[1,2-a]indole-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.2703    3.0897   -1.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    1.3157   -1.5788 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003    1.0331    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3355    1.6009    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2999    0.5490    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    0.4692    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1914   -0.8070   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -1.9194    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1413   -1.9493    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0465   -2.8922    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392   -0.6984    0.9404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2017   -0.3911    0.5179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.2295    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -2.4776    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -0.6095    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.3841    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.8437    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -0.0204    1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4432    0.4700    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566    0.1324    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652   -0.6933   -0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893   -1.1901   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    0.7946    0.5400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    1.5875    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.7264    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769    3.5422   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    3.3202   -2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    3.6502   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    1.5501    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.6042    0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0938    1.3737   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -0.8003   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0291   -2.8844   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -2.4298   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -3.8037    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884   -0.6494    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -2.4868    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    0.2646    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    1.1176    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    0.5310    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780   -0.9745   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374   -1.8396   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.2517    0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 24 25  2  0
 12  3  1  0
 22 17  1  0
 24  3  1  0
 11  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 11 36  1  1
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  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      -1.270   3.090  -1.914  0.00  0.00           C+0
HETATM    2  S   UNK     0      -1.310   1.316  -1.579  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.100   1.033   0.176  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.336   1.601   0.887  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.300   0.549   0.539  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.515   0.469   0.118  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.191  -0.807  -0.150  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.528  -1.919   0.033  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.141  -1.949   0.485  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.046  -2.892   1.541  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.539  -0.698   0.940  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.202  -0.391   0.518  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.058  -1.230   0.424  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.112  -2.478   0.329  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.287  -0.610   0.436  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.337  -1.384   0.320  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.674  -0.844   0.332  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.152  -0.020   1.314  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.443   0.470   1.233  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.257   0.132   0.164  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.765  -0.693  -0.812  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.489  -1.190  -0.752  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.363   0.795   0.540  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.164   1.587   0.633  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.246   2.726   1.103  0.00  0.00           O+0
HETATM   26  H   UNK     0      -2.277   3.542  -1.978  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.784   3.320  -2.889  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.694   3.650  -1.142  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.131   1.550   1.976  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.600   2.604   0.526  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.094   1.374  -0.057  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.239  -0.800  -0.496  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.029  -2.884  -0.158  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.505  -2.430  -0.328  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.255  -3.804   1.196  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.588  -0.649   2.080  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.203  -2.487   0.210  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.559   0.265   2.188  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.828   1.118   2.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       7.262   0.531   0.129  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.378  -0.975  -1.660  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.137  -1.840  -1.542  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.301   1.252   0.529  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12   24                                             
CONECT    4    3    5   29   30                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   33                                                  
CONECT    9    8   10   11   34                                             
CONECT   10    9   35                                                       
CONECT   11    9   12    5   36                                             
CONECT   12   11   13    3                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17   37                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   39                                                  
CONECT   20   19   21   40                                                  
CONECT   21   20   22   41                                                  
CONECT   22   21   17   42                                                  
CONECT   23   15   24   43                                                  
CONECT   24   23   25    3                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   16                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

RDKit          3D

43 46  0  0  0  0  0  0  0  0999 V2000
   -1.2703    3.0897   -1.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    1.3157   -1.5788 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003    1.0331    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3355    1.6009    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2999    0.5490    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146    0.4692    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1914   -0.8070   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -1.9194    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1413   -1.9493    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0465   -2.8922    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392   -0.6984    0.9404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2017   -0.3911    0.5179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.2295    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -2.4776    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -0.6095    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.3841    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.8437    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -0.0204    1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4432    0.4700    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566    0.1324    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652   -0.6933   -0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893   -1.1901   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    0.7946    0.5400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641    1.5875    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.7264    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769    3.5422   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    3.3202   -2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    3.6502   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    1.5501    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.6042    0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0938    1.3737   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -0.8003   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0291   -2.8844   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -2.4298   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -3.8037    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884   -0.6494    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -2.4868    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    0.2646    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    1.1176    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    0.5310    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780   -0.9745   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374   -1.8396   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.2517    0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 24 25  2  0
 12  3  1  0
 22 17  1  0
 24  3  1  0
 11  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 11 36  1  1
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3Z,5AS,6S,10ar)-1,6-dihydroxy-10a-(methylsulphanyl)-3-(phenylmethylidene)-3H,4H,5ah,6H,10H,10ah-pyrazino[1,2-a]indol-4-one	Generator
(3Z,5AS,6S,10ar)-bis(dethio)-3a-deoxy-2-demethyl-10a-methylthio-3a-phenyl-3,3a-didehydrogliotoxin	MeSH

Chemical Formula

C₁₉H₁₈N₂O₃S

Average Mass

354.4200 Da

Monoisotopic Mass

354.10381 Da

IUPAC Name

(3Z,5aS,6S,10aR)-6-hydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-1H,2H,3H,4H,5aH,6H,10H,10aH-pyrazino[1,2-a]indole-1,4-dione

Traditional Name

(3Z,5aS,6S,10aR)-6-hydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-2H,5aH,6H,10H-pyrazino[1,2-a]indole-1,4-dione

CAS Registry Number

Not Available

SMILES

CS[C@@]12CC3=CC=C[C@H](O)[C@H]3N1C(=O)\C(NC2=O)=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H18N2O3S/c1-25-19-11-13-8-5-9-15(22)16(13)21(19)17(23)14(20-18(19)24)10-12-6-3-2-4-7-12/h2-10,15-16,22H,11H2,1H3,(H,20,24)/b14-10-/t15-,16-,19+/m0/s1

InChI Key

JDNKAJXFWBFPPM-TUGLFXRSSA-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
Phoma sp. OUCMDZ-1847	NPAtlas	24370114

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Indole or derivatives
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Sulfenyl compound
Azacycle
Dialkylthioether
Organoheterocyclic compound
Hemithioaminal
Thioether
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
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	1.85	ALOGPS
logP	1.6	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.21 m³·mol⁻¹	ChemAxon
Polarizability	37.29 Å³	ChemAxon
Number of Rings	4	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

NPA000740

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31126180

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76335556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phomazine A (NP0012356)

MOL for NP0012356 (Phomazine A)

3D MOL for NP0012356 (Phomazine A)

3D SDF for NP0012356 (Phomazine A)

3D-SDF for NP0012356 (Phomazine A)

PDB for NP0012356 (Phomazine A)

3D PDB for NP0012356 (Phomazine A)

SMILES for NP0012356 (Phomazine A)

INCHI for NP0012356 (Phomazine A)

Structure for NP0012356 (Phomazine A)

3D Structure for NP0012356 (Phomazine A)