NP-MRD: Showing NP-Card for Circumdatin G (NP0003601)

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Record Information

Version

1.0

Created at

2020-12-09 00:48:21 UTC

Updated at

2021-07-15 16:46:51 UTC

NP-MRD ID

NP0003601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Circumdatin G

Provided By

NPAtlas

Description

(10S)-8,14-dihydroxy-10-methyl-1,9,12-triazatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-2,4,6,8,11,13(18),14,16-octaen-19-one belongs to the class of organic compounds known as pyrimidodiazepines. Pyrimidodiazepines are compounds containing a pyrimidoazepine moiety, which consists of a pyrimidine fused to a piperazine ring by a bond. Pyrimidine is 6-membered ring consisting of five carbon atoms and two nitrogen atoms at ring positions 1 and 3. Diazepine is a 7-membered ring consisting of five carbon atoms and two nitrogen centers. Circumdatin G is found in Aspergillus ochraceus and Exophiala sp.. It was first documented in 2001 (PMID: 11170686). Based on a literature review very few articles have been published on (10S)-8,14-dihydroxy-10-methyl-1,9,12-triazatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-2,4,6,8,11,13(18),14,16-octaen-19-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 36 39  0  0  0  0            999 V2000
   -0.3219   -3.3225    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -2.0201    0.4745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9541   -2.0272   -0.6272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.9531   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -1.1221   -1.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882    0.4213   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549    1.1453   -0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    2.4201   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    2.9512    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    2.2636    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    1.0092    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    0.4086    0.0668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -0.9080    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -1.3149    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990   -0.4519    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.8398    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -2.1773    0.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    0.0769   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.3966   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094    1.8238   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.8858   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    1.3222   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    2.5086   -0.3696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.8010   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -4.0093    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -3.1424    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.7626    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.8878   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7126    0.6477   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    2.9892   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    3.9605    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.6625    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -2.8588    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6512   -0.2806   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    2.1320   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    2.8542   -0.5129 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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 13  2  1  0  0  0  0
 21 15  1  0  0  0  0
 11  6  1  0  0  0  0
 22 12  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
  2 27  1  1  0  0  0
  3 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
M  END

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -0.3219   -3.3225    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -2.0201    0.4745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9541   -2.0272   -0.6272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.9531   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -1.1221   -1.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882    0.4213   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549    1.1453   -0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    2.4201   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    2.9512    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    2.2636    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    1.0092    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    0.4086    0.0668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -0.9080    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -1.3149    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990   -0.4519    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.8398    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -2.1773    0.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    0.0769   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.3966   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094    1.8238   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.8858   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    1.3222   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    2.5086   -0.3696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.8010   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -4.0093    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -3.1424    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.7626    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.8878   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7126    0.6477   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    2.9892   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    3.9605    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.6625    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -2.8588    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6512   -0.2806   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    2.1320   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    2.8542   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 13  2  1  0
 21 15  1  0
 11  6  1  0
 22 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv1652306242117483D          

 36 39  0  0  0  0            999 V2000
   -0.3219   -3.3225    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -2.0201    0.4745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9541   -2.0272   -0.6272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.9531   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -1.1221   -1.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882    0.4213   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549    1.1453   -0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    2.4201   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    2.9512    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    2.2636    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    1.0092    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    0.4086    0.0668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -0.9080    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -1.3149    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990   -0.4519    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.8398    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -2.1773    0.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    0.0769   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.3966   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094    1.8238   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.8858   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    1.3222   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    2.5086   -0.3696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.8010   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -4.0093    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -3.1424    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.7626    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.8878   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7126    0.6477   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    2.9892   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    3.9605    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.6625    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -2.8588    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6512   -0.2806   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    2.1320   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    2.8542   -0.5129 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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 13  2  1  0  0  0  0
 21 15  1  0  0  0  0
 11  6  1  0  0  0  0
 22 12  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
  2 27  1  1  0  0  0
  3 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2N=C3N(C(=O)C2=C([H])C([H])=C1[H])C1=C([H])C([H])=C([H])C([H])=C1C(=O)N([H])[C@@]3([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H13N3O3/c1-9-15-19-14-11(6-4-8-13(14)21)17(23)20(15)12-7-3-2-5-10(12)16(22)18-9/h2-9,21H,1H3,(H,18,22)/t9-/m0/s1

> <INCHI_KEY>
VNCYXASDDCJEJE-VIFPVBQESA-N

> <FORMULA>
C17H13N3O3

> <MOLECULAR_WEIGHT>
307.309

> <EXACT_MASS>
307.095691291

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.588266918728827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10S)-14-hydroxy-10-methyl-1,9,12-triazatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-2,4,6,11,13,15,17-heptaene-8,19-dione

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.6959193190000001

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.307862238941578

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.550744153991155

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6331855708954164

> <JCHEM_POLAR_SURFACE_AREA>
82.0

> <JCHEM_REFRACTIVITY>
85.955

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10S)-14-hydroxy-10-methyl-1,9,12-triazatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-2,4,6,11,13,15,17-heptaene-8,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -0.3219   -3.3225    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -2.0201    0.4745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9541   -2.0272   -0.6272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.9531   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -1.1221   -1.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882    0.4213   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549    1.1453   -0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    2.4201   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    2.9512    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    2.2636    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    1.0092    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    0.4086    0.0668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -0.9080    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -1.3149    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990   -0.4519    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.8398    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -2.1773    0.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    0.0769   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.3966   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094    1.8238   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.8858   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    1.3222   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    2.5086   -0.3696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.8010   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -4.0093    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -3.1424    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.7626    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.8878   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7126    0.6477   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    2.9892   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    3.9605    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.6625    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -2.8588    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6512   -0.2806   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    2.1320   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    2.8542   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 13  2  1  0
 21 15  1  0
 11  6  1  0
 22 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  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      -0.322  -3.322   0.667  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.996  -2.020   0.475  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.954  -2.027  -0.627  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.799  -0.953  -1.003  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.727  -1.122  -1.812  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.688   0.421  -0.507  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.855   1.145  -0.521  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.873   2.420  -0.002  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.715   2.951   0.526  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.510   2.264   0.565  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.521   1.009   0.041  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.232   0.409   0.067  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.008  -0.908   0.300  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.284  -1.315   0.324  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.299  -0.452   0.123  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.620  -0.840   0.143  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.932  -2.177   0.381  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.617   0.077  -0.068  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.335   1.397  -0.303  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.009   1.824  -0.330  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.037   0.886  -0.117  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.708   1.322  -0.145  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.450   2.509  -0.370  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.035  -3.801  -0.293  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.934  -4.009   1.312  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.614  -3.142   1.264  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.571  -1.763   1.385  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.047  -2.888  -1.207  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.713   0.648  -0.954  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.809   2.989  -0.019  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.692   3.961   0.948  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.650   2.663   1.033  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.208  -2.859   0.537  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.651  -0.281  -0.042  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.117   2.132  -0.471  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.755   2.854  -0.513  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3   13   27                                             
CONECT    3    2    4   28                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14    2                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   33                                                       
CONECT   18   16   19   34                                                  
CONECT   19   18   20   35                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20   22   15                                                  
CONECT   22   21   23   12                                                  
CONECT   23   22                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

RDKit          3D

36 39  0  0  0  0  0  0  0  0999 V2000
   -0.3219   -3.3225    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -2.0201    0.4745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9541   -2.0272   -0.6272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.9531   -1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -1.1221   -1.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6882    0.4213   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549    1.1453   -0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733    2.4201   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    2.9512    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    2.2636    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    1.0092    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    0.4086    0.0668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -0.9080    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -1.3149    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990   -0.4519    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.8398    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -2.1773    0.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    0.0769   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.3966   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094    1.8238   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.8858   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    1.3222   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    2.5086   -0.3696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.8010   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -4.0093    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -3.1424    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.7626    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.8878   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7126    0.6477   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    2.9892   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    3.9605    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.6625    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -2.8588    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6512   -0.2806   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    2.1320   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    2.8542   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 13  2  1  0
 21 15  1  0
 11  6  1  0
 22 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃N₃O₃

Average Mass

307.3090 Da

Monoisotopic Mass

307.09569 Da

IUPAC Name

(10S)-14-hydroxy-10-methyl-1,9,12-triazatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-2,4,6,11,13,15,17-heptaene-8,19-dione

Traditional Name

(10S)-14-hydroxy-10-methyl-1,9,12-triazatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-2,4,6,11,13,15,17-heptaene-8,19-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1NC(=O)C2=CC=CC=C2N2C(=O)C3=C(N=C12)C(O)=CC=C3

InChI Identifier

InChI=1S/C17H13N3O3/c1-9-15-19-14-11(6-4-8-13(14)21)17(23)20(15)12-7-3-2-5-10(12)16(22)18-9/h2-9,21H,1H3,(H,18,22)/t9-/m0/s1

InChI Key

VNCYXASDDCJEJE-VIFPVBQESA-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 ochraceus	NPAtlas	11170686
Exophiala sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidodiazepines. Pyrimidodiazepines are compounds containing a pyrimidoazepine moiety, which consists of a pyrimidine fused to a piperazine ring by a bond. Pyrimidine is 6-membered ring consisting of five carbon atoms and two nitrogen atoms at ring positions 1 and 3. Diazepine is a 7-membered ring consisting of five carbon atoms and two nitrogen centers.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrimidodiazepines

Sub Class

Not Available

Direct Parent

Pyrimidodiazepines

Alternative Parents

Substituents

Benzodiazepine
Pyrimidodiazepine
1,4-benzodiazepine
Quinazoline
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyrimidone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Lactam
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	1.47	ALOGPS
logP	1.7	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.96 m³·mol⁻¹	ChemAxon
Polarizability	31.59 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

NPA013780

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8979942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10804637

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dai J, Carte BK, Sidebottom PJ, Sek Yew AL, Ng S, Huang Y, Butler MS: Circumdatin G, a new alkaloid from the fungus Aspergillus ochraceus. J Nat Prod. 2001 Jan;64(1):125-6. doi: 10.1021/np000381u. [PubMed:11170686 ]

Showing NP-Card for Circumdatin G (NP0003601)

MOL for NP0003601 (Circumdatin G)

3D MOL for NP0003601 (Circumdatin G)

3D SDF for NP0003601 (Circumdatin G)

3D-SDF for NP0003601 (Circumdatin G)

PDB for NP0003601 (Circumdatin G)

3D PDB for NP0003601 (Circumdatin G)

SMILES for NP0003601 (Circumdatin G)

INCHI for NP0003601 (Circumdatin G)

Structure for NP0003601 (Circumdatin G)

3D Structure for NP0003601 (Circumdatin G)