NP-MRD: Showing NP-Card for Sclerotigenin (NP0001617)

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Record Information

Version

1.0

Created at

2020-09-23 01:58:48 UTC

Updated at

2021-08-10 02:55:43 UTC

NP-MRD ID

NP0001617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sclerotigenin

Provided By

NPAtlas

Description

8-Hydroxy-1,9,12-triazatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-2,4,6,8,11,13,15,17-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. Sclerotigenin is found in Penicillium and Penicillium commune. It was first documented in 1999 (PMID: 10217735). Based on a literature review very few articles have been published on 8-hydroxy-1,9,12-triazatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-2,4,6,8,11,13,15,17-octaen-19-one (PMID: 31013089) (PMID: 19137180) (PMID: 20066279) (PMID: 22334340) (PMID: 20000772) (PMID: 17479166).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

 32 35  0  0  0  0            999 V2000
   -3.5236    2.2754   -1.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.8395   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    2.7015    0.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296    2.4215    1.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3244    1.2408    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6330    1.4719    0.4933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.5404    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8768    0.7903   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7374   -0.1791   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.4036   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -1.6483   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6730   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453   -0.9421   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -2.0333   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.0133    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -0.4128    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.7342    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.2796    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.4986    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -0.1624   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.3911   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    3.6844   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206    2.3188    2.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    3.3023    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298    1.7457    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960    0.0192   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992   -2.1618   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -2.5885   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -2.3024    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094   -3.3152    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -1.9270    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837    0.5061   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 16 17  2  0  0  0  0
 17 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  2  1  0  0  0  0
 15  5  1  0  0  0  0
 21 16  1  0  0  0  0
 12  7  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  8 25  1  0  0  0  0
  9 26  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  1  0  0  0  0
 17 29  1  0  0  0  0
 18 30  1  0  0  0  0
 19 31  1  0  0  0  0
 20 32  1  0  0  0  0
M  END

     RDKit          3D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.5236    2.2754   -1.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.8395   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    2.7015    0.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296    2.4215    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    1.2408    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6330    1.4719    0.4933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.5404    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8768    0.7903   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7374   -0.1791   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.4036   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -1.6483   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6730   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453   -0.9421   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -2.0333   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.0133    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -0.4128    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.7342    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.2796    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.4986    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -0.1624   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.3911   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    3.6844   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206    2.3188    2.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    3.3023    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298    1.7457    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960    0.0192   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992   -2.1618   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -2.5885   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -2.3024    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094   -3.3152    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -1.9270    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837    0.5061   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 15  5  1  0
 21 16  1  0
 12  7  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv1652306242117443D          

 32 35  0  0  0  0            999 V2000
   -3.5236    2.2754   -1.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.8395   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    2.7015    0.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296    2.4215    1.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3244    1.2408    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6330    1.4719    0.4933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.5404    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8768    0.7903   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7374   -0.1791   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.4036   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -1.6483   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6730   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453   -0.9421   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -2.0333   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.0133    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -0.4128    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.7342    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.2796    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.4986    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -0.1624   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.3911   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    3.6844   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206    2.3188    2.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    3.3023    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298    1.7457    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960    0.0192   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992   -2.1618   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -2.5885   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -2.3024    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094   -3.3152    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -1.9270    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837    0.5061   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 16 17  2  0  0  0  0
 17 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  2  1  0  0  0  0
 15  5  1  0  0  0  0
 21 16  1  0  0  0  0
 12  7  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  8 25  1  0  0  0  0
  9 26  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  1  0  0  0  0
 17 29  1  0  0  0  0
 18 30  1  0  0  0  0
 19 31  1  0  0  0  0
 20 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)C2=C([H])C([H])=C([H])C([H])=C2N2C(=O)C3=C([H])C([H])=C([H])C([H])=C3N=C2C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H11N3O2/c20-15-11-6-2-4-8-13(11)19-14(9-17-15)18-12-7-3-1-5-10(12)16(19)21/h1-8H,9H2,(H,17,20)

> <INCHI_KEY>
NGYKOTTXJAPLPC-UHFFFAOYSA-N

> <FORMULA>
C16H11N3O2

> <MOLECULAR_WEIGHT>
277.283

> <EXACT_MASS>
277.085126606

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.65352793139983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
1.17

> <JCHEM_LOGP>
1.430720398333333

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.938288774625647

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.202076431361274

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4388682595111693

> <JCHEM_POLAR_SURFACE_AREA>
61.77

> <JCHEM_REFRACTIVITY>
79.48020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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

 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.5236    2.2754   -1.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.8395   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    2.7015    0.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296    2.4215    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    1.2408    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6330    1.4719    0.4933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.5404    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8768    0.7903   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7374   -0.1791   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.4036   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -1.6483   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6730   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453   -0.9421   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -2.0333   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.0133    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -0.4128    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.7342    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.2796    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.4986    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -0.1624   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.3911   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    3.6844   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206    2.3188    2.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    3.3023    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298    1.7457    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960    0.0192   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992   -2.1618   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -2.5885   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -2.3024    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094   -3.3152    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -1.9270    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837    0.5061   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 15  5  1  0
 21 16  1  0
 12  7  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  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  O   UNK     0      -3.524   2.275  -1.036  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.591   1.839  -0.359  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.574   2.701   0.147  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.430   2.422   1.006  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.324   1.241   0.554  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.633   1.472   0.493  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.499   0.540   0.042  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.877   0.790  -0.018  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.737  -0.179  -0.484  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.223  -1.404  -0.892  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.843  -1.648  -0.830  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.992  -0.673  -0.363  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.645  -0.942  -0.313  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.218  -2.033  -0.694  0.00  0.00           O+0
HETATM   15  N   UNK     0      -0.152   0.013   0.144  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.511  -0.413   0.171  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.608  -1.734   0.473  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.878  -2.280   0.473  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -1.499   0.179  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.858  -0.162  -0.118  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.622   0.391  -0.123  0.00  0.00           C+0
HETATM   22  H   UNK     0      -1.662   3.684  -0.140  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.721   2.319   2.070  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.239   3.302   0.951  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.230   1.746   0.306  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.796   0.019  -0.527  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.899  -2.162  -1.256  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.428  -2.588  -1.141  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.772  -2.302   0.760  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.009  -3.315   0.702  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.988  -1.927   0.179  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.684   0.506  -0.357  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   23   24                                             
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16    5                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   21   32                                                  
CONECT   21   20    2   16                                                  
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    4                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

RDKit          3D

32 35  0  0  0  0  0  0  0  0999 V2000
   -3.5236    2.2754   -1.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.8395   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    2.7015    0.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296    2.4215    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    1.2408    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6330    1.4719    0.4933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.5404    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8768    0.7903   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7374   -0.1791   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.4036   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -1.6483   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6730   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453   -0.9421   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -2.0333   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.0133    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114   -0.4128    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.7342    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.2796    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.4986    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -0.1624   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.3911   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    3.6844   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206    2.3188    2.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    3.3023    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298    1.7457    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960    0.0192   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992   -2.1618   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -2.5885   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -2.3024    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094   -3.3152    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -1.9270    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837    0.5061   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 15  5  1  0
 21 16  1  0
 12  7  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₁₁N₃O₂

Average Mass

277.2830 Da

Monoisotopic Mass

277.08513 Da

IUPAC Name

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

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

[H]N1C(=O)C2=C([H])C([H])=C([H])C([H])=C2N2C(=O)C3=C([H])C([H])=C([H])C([H])=C3N=C2C1([H])[H]

InChI Identifier

InChI=1S/C16H11N3O2/c20-15-11-6-2-4-8-13(11)19-14(9-17-15)18-12-7-3-1-5-10(12)16(19)21/h1-8H,9H2,(H,17,20)

InChI Key

NGYKOTTXJAPLPC-UHFFFAOYSA-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
Penicillium	NPAtlas	10217735
Penicillium commune	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Penicillium nordicum	KNApSAcK Database	22123792
Penicillium sclerotigenum	KNApSAcK Database	22123792

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
Pyrimidone
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.17	ALOGPS
logP	1.43	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.48 m³·mol⁻¹	ChemAxon
Polarizability	28.65 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

NPA002655

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026251

Chemspider ID

8977775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10802469

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Joshi BK, Gloer JB, Wicklow DT, Dowd PF: Sclerotigenin: A new antiinsectan benzodiazepine from the sclerotia of penicillium sclerotigenum J Nat Prod. 1999 Apr;62(4):650-2. doi: 10.1021/np980511n. [PubMed:10217735 ]
Li J, Hu Y, Hao X, Tan J, Li F, Qiao X, Chen S, Xiao C, Chen M, Peng Z, Gan M: Raistrickindole A, an Anti-HCV Oxazinoindole Alkaloid from Penicillium raistrickii IMB17-034. J Nat Prod. 2019 May 24;82(5):1391-1395. doi: 10.1021/acs.jnatprod.9b00259. Epub 2019 Apr 23. [PubMed:31013089 ]
Tseng MC, Lai CY, Chu YW, Chu YH: Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines. Chem Commun (Camb). 2009 Jan 28;(4):445-7. doi: 10.1039/b813880j. Epub 2008 Nov 19. [PubMed:19137180 ]
Tseng MC, Yang HY, Chu YH: Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones. Org Biomol Chem. 2010 Jan 21;8(2):419-27. doi: 10.1039/b910545j. Epub 2009 Nov 5. [PubMed:20066279 ]
Fang J, Zhou J: Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis. Org Biomol Chem. 2012 Mar 28;10(12):2389-91. doi: 10.1039/c2ob07178a. Epub 2012 Feb 15. [PubMed:22334340 ]
Lu Y, Nagashima T, Miriyala B, Conde J, Zhang W: Fluorous synthesis of substituted sclerotigenin library. J Comb Chem. 2010 Jan-Feb;12(1):125-8. doi: 10.1021/cc9001636. [PubMed:20000772 ]
Zhang W, Williams JP, Lu Y, Nagashima T, Chu Q: Fluorous synthesis of sclerotigenin-type benzodiazepine-quinazolinones. Tetrahedron Lett. 2007 Jan 22;48(4):563-565. doi: 10.1016/j.tetlet.2006.11.127. [PubMed:17479166 ]
Liu JF, Kaselj M, Isome Y, Chapnick J, Zhang B, Bi G, Yohannes D, Yu L, Baldino CM: Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids. J Org Chem. 2005 Dec 9;70(25):10488-93. doi: 10.1021/jo051876x. [PubMed:16323862 ]
Larsen TO, Gareis M, Frisvad JC: Cell cytotoxicity and mycotoxin and secondary metabolite production by common penicillia on cheese agar. J Agric Food Chem. 2002 Oct 9;50(21):6148-52. doi: 10.1021/jf020453i. [PubMed:12358494 ]

Showing NP-Card for Sclerotigenin (NP0001617)

MOL for NP0001617 (Sclerotigenin)

3D MOL for NP0001617 (Sclerotigenin)

3D SDF for NP0001617 (Sclerotigenin)

3D-SDF for NP0001617 (Sclerotigenin)

PDB for NP0001617 (Sclerotigenin)

3D PDB for NP0001617 (Sclerotigenin)

SMILES for NP0001617 (Sclerotigenin)

INCHI for NP0001617 (Sclerotigenin)

Structure for NP0001617 (Sclerotigenin)

3D Structure for NP0001617 (Sclerotigenin)