NP-MRD: Showing NP-Card for Glionitrin A (NP0008211)

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Record Information

Version

2.0

Created at

2020-12-09 05:51:43 UTC

Updated at

2021-07-15 16:59:45 UTC

NP-MRD ID

NP0008211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glionitrin A

Provided By

NPAtlas

Description

Glionitrin A 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. Glionitrin A is found in Aspergillus and Aspergillus fumigatus. Glionitrin A was first documented in 2009 (PMID: 19159274). Based on a literature review very few articles have been published on Glionitrin A (PMID: 21954885) (PMID: 22947415) (PMID: 24583858).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106083D          

 34 37  0  0  0  0            999 V2000
   -3.8156   -0.6258   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -0.6122   -0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.4938   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -2.2632   -1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -1.5129    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8956   -2.2295   -0.3839 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0153   -1.2246   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -1.3333   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.2219   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.0035   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622    2.1136   -0.0413 N   0  3  0  0  0  4  0  0  0  0  0  0
    5.7515    1.9817   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750    3.3097    0.3941 O   0  5  0  0  0  1  0  0  0  0  0  0
    2.3509    1.1048    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.0017    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -0.0968    0.3646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7854    0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    1.9801    1.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086    0.3229    0.8306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2293    1.4592    0.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1624    2.1958   -0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -0.7208    2.3487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -2.0794    1.8807 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -0.7521   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010    0.2630   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417   -1.5063   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -3.1394    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -2.5493   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189   -2.2901   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -0.3178   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652    2.0489    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.1241    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773    1.2204    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    3.0578   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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  2  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  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19  2  1  0  0  0  0
 16  5  1  0  0  0  0
  5 23  1  1  0  0  0
 15  7  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
 14 31  1  0  0  0  0
 20 32  1  0  0  0  0
 20 33  1  0  0  0  0
 21 34  1  0  0  0  0
M  CHG  2  11   1  13  -1
M  END

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.8156   -0.6258   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -0.6122   -0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.4938   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -2.2632   -1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -1.5129    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8956   -2.2295   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -1.2246   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -1.3333   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.2219   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.0035   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622    2.1136   -0.0413 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7515    1.9817   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750    3.3097    0.3941 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.3509    1.1048    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.0017    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -0.0968    0.3646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7854    0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    1.9801    1.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086    0.3229    0.8306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2293    1.4592    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624    2.1958   -0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -0.7208    2.3487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -2.0794    1.8807 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -0.7521   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010    0.2630   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417   -1.5063   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -3.1394    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -2.5493   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189   -2.2901   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -0.3178   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652    2.0489    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.1241    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773    1.2204    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    3.0578   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 20 21  1  0
 19 22  1  0
 22 23  1  0
 19  2  1  0
 16  5  1  0
  5 23  1  1
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 14 31  1  0
 20 32  1  0
 20 33  1  0
 21 34  1  0
M  CHG  2  11   1  13  -1
M  END


  Mrv1652306242106083D          

 34 37  0  0  0  0            999 V2000
   -3.8156   -0.6258   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -0.6122   -0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.4938   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -2.2632   -1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -1.5129    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8956   -2.2295   -0.3839 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0153   -1.2246   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -1.3333   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.2219   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.0035   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622    2.1136   -0.0413 N   0  3  0  0  0  4  0  0  0  0  0  0
    5.7515    1.9817   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750    3.3097    0.3941 O   0  5  0  0  0  1  0  0  0  0  0  0
    2.3509    1.1048    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.0017    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -0.0968    0.3646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7854    0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    1.9801    1.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086    0.3229    0.8306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2293    1.4592    0.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1624    2.1958   -0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -0.7208    2.3487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -2.0794    1.8807 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -0.7521   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010    0.2630   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417   -1.5063   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -3.1394    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -2.5493   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189   -2.2901   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -0.3178   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652    2.0489    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.1241    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773    1.2204    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    3.0578   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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  2  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  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19  2  1  0  0  0  0
 16  5  1  0  0  0  0
  5 23  1  1  0  0  0
 15  7  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
 14 31  1  0  0  0  0
 20 32  1  0  0  0  0
 20 33  1  0  0  0  0
 21 34  1  0  0  0  0
M  CHG  2  11   1  13  -1
M  END
> <DATABASE_ID>
NP0008211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]12SS[C@]3(N(C4=C([H])C(=C([H])C([H])=C4C3([H])[H])[N+]([O-])=O)C1=O)C(=O)N2C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H11N3O5S2/c1-14-10(18)12-5-7-2-3-8(16(20)21)4-9(7)15(12)11(19)13(14,6-17)23-22-12/h2-4,17H,5-6H2,1H3/t12-,13-/m0/s1

> <INCHI_KEY>
VRFJINVAZRAFHH-STQMWFEESA-N

> <FORMULA>
C13H11N3O5S2

> <MOLECULAR_WEIGHT>
353.37

> <EXACT_MASS>
353.014012814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
32.38445220995179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(1S,11S)-11-(hydroxymethyl)-15-methyl-10,14-dioxo-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-trien-6-yl]nitro}-lambda1-oxidanyl

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
1.5372006423333335

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.091339818598662

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1962479633449448

> <JCHEM_POLAR_SURFACE_AREA>
103.99

> <JCHEM_REFRACTIVITY>
84.24400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,11S)-11-(hydroxymethyl)-15-methyl-10,14-dioxo-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-trien-6-ylnitro]-lambda1-oxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.8156   -0.6258   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -0.6122   -0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.4938   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -2.2632   -1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -1.5129    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8956   -2.2295   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -1.2246   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -1.3333   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.2219   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.0035   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622    2.1136   -0.0413 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7515    1.9817   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750    3.3097    0.3941 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.3509    1.1048    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.0017    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -0.0968    0.3646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7854    0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    1.9801    1.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086    0.3229    0.8306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2293    1.4592    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624    2.1958   -0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -0.7208    2.3487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -2.0794    1.8807 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -0.7521   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010    0.2630   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417   -1.5063   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -3.1394    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -2.5493   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189   -2.2901   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -0.3178   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652    2.0489    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.1241    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773    1.2204    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    3.0578   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 20 21  1  0
 19 22  1  0
 22 23  1  0
 19  2  1  0
 16  5  1  0
  5 23  1  1
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 14 31  1  0
 20 32  1  0
 20 33  1  0
 21 34  1  0
M  CHG  2  11   1  13  -1
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      -3.816  -0.626  -0.908  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.536  -0.612  -0.240  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.484  -1.494  -0.603  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.615  -2.263  -1.612  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.214  -1.513   0.211  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.896  -2.229  -0.384  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.015  -1.225  -0.367  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.346  -1.333  -0.699  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.148  -0.222  -0.580  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.693   1.004  -0.144  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.562   2.114  -0.041  0.00  0.00           N+1
HETATM   12  O   UNK     0       5.752   1.982  -0.348  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.075   3.310   0.394  0.00  0.00           O-1
HETATM   14  C   UNK     0       2.351   1.105   0.189  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.535  -0.002   0.075  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.148  -0.097   0.365  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.900   0.785   0.741  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.658   1.980   1.007  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.309   0.323   0.831  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.229   1.459   0.905  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.162   2.196  -0.248  0.00  0.00           O+0
HETATM   22  S   UNK     0      -2.326  -0.721   2.349  0.00  0.00           S+0
HETATM   23  S   UNK     0      -0.702  -2.079   1.881  0.00  0.00           S+0
HETATM   24  H   UNK     0      -3.681  -0.752  -2.012  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.401   0.263  -0.685  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.442  -1.506  -0.599  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.252  -3.139   0.176  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.688  -2.549  -1.442  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.719  -2.290  -1.044  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.189  -0.318  -0.844  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.965   2.049   0.533  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.893   2.124   1.740  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.277   1.220   1.111  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.690   3.058  -0.128  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16   23                                             
CONECT    6    5    7   27   28                                             
CONECT    7    6    8   15                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10   30                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   31                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22    2                                             
CONECT   20   19   21   32   33                                             
CONECT   21   20   34                                                       
CONECT   22   19   23                                                       
CONECT   23   22    5                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    6                                                            
CONECT   28    6                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31   14                                                            
CONECT   32   20                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

RDKit          3D

34 37  0  0  0  0  0  0  0  0999 V2000
   -3.8156   -0.6258   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -0.6122   -0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.4938   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -2.2632   -1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -1.5129    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8956   -2.2295   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -1.2246   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -1.3333   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.2219   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.0035   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622    2.1136   -0.0413 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7515    1.9817   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750    3.3097    0.3941 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.3509    1.1048    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.0017    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -0.0968    0.3646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7854    0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    1.9801    1.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086    0.3229    0.8306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2293    1.4592    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624    2.1958   -0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -0.7208    2.3487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -2.0794    1.8807 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -0.7521   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010    0.2630   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417   -1.5063   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -3.1394    0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -2.5493   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189   -2.2901   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -0.3178   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652    2.0489    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.1241    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773    1.2204    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    3.0578   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 20 21  1  0
 19 22  1  0
 22 23  1  0
 19  2  1  0
 16  5  1  0
  5 23  1  1
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 14 31  1  0
 20 32  1  0
 20 33  1  0
 21 34  1  0
M  CHG  2  11   1  13  -1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₃H₁₁N₃O₅S₂

Average Mass

353.3700 Da

Monoisotopic Mass

353.01401 Da

IUPAC Name

{[(1S,11S)-11-(hydroxymethyl)-15-methyl-10,14-dioxo-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-trien-6-yl]nitro}-lambda1-oxidanyl

Traditional Name

[(1S,11S)-11-(hydroxymethyl)-15-methyl-10,14-dioxo-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-trien-6-ylnitro]-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@@]23CC4=C(C=C(C=C4)[N+]([O-])=O)N2C(=O)[C@]1(CO)SS3

InChI Identifier

InChI=1S/C13H11N3O5S2/c1-14-10(18)12-5-7-2-3-8(16(20)21)4-9(7)15(12)11(19)13(14,6-17)23-22-12/h2-4,17H,5-6H2,1H3/t12-,13-/m0/s1

InChI Key

VRFJINVAZRAFHH-STQMWFEESA-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
Aspergillus	NPAtlas	19159274
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	0.59	ALOGPS
logP	1.54	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.24 m³·mol⁻¹	ChemAxon
Polarizability	32.38 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

NPA005355

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28286042

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glionitrin A

METLIN ID

Not Available

PubChem Compound

25243252

PDB ID

Not Available

ChEBI ID

65967

Good Scents ID

Not Available

References

General References

Park HB, Kwon HC, Lee CH, Yang HO: Glionitrin A, an antibiotic-antitumor metabolite derived from competitive interaction between abandoned mine microbes. J Nat Prod. 2009 Feb 27;72(2):248-52. doi: 10.1021/np800606e. [PubMed:19159274 ]
Park HB, Kim YJ, Park JS, Yang HO, Lee KR, Kwon HC: Glionitrin B, a cancer invasion inhibitory diketopiperazine produced by microbial coculture. J Nat Prod. 2011 Oct 28;74(10):2309-12. doi: 10.1021/np200563x. Epub 2011 Sep 28. [PubMed:21954885 ]
Lee SH, Yang HO, Kwon HC, Jung BH: Identification of the urinary metabolites of glionitrin A in rats using ultra-performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Oct 1;906:33-40. doi: 10.1016/j.jchromb.2012.08.015. Epub 2012 Aug 21. [PubMed:22947415 ]
Kim YJ, Park HB, Yoo JH, Kwon HC, Kim J, Yang HO: Glionitrin A, a new diketopiperazine disulfide, activates ATM-ATR-Chk1/2 via 53BP1 phosphorylation in DU145 cells and shows antitumor effect in xenograft model. Biol Pharm Bull. 2014;37(3):378-86. doi: 10.1248/bpb.b13-00719. [PubMed:24583858 ]

Showing NP-Card for Glionitrin A (NP0008211)

MOL for NP0008211 (Glionitrin A)

3D MOL for NP0008211 (Glionitrin A)

3D SDF for NP0008211 (Glionitrin A)

3D-SDF for NP0008211 (Glionitrin A)

PDB for NP0008211 (Glionitrin A)

3D PDB for NP0008211 (Glionitrin A)

SMILES for NP0008211 (Glionitrin A)

INCHI for NP0008211 (Glionitrin A)

Structure for NP0008211 (Glionitrin A)

3D Structure for NP0008211 (Glionitrin A)