NP-MRD: Showing NP-Card for 16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile (NP0237692)

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Record Information

Version

2.0

Created at

2022-09-06 20:54:42 UTC

Updated at

2022-09-06 20:54:43 UTC

NP-MRD ID

NP0237692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile

Description

Cyanocycline A belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton. 16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile is found in Streptomyces flavogriseus, Streptomyces flavovirens and Streptomyces lusitanus. Cyanocycline A is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251523452D          

 31 36  0  0  0  0            999 V2000
    7.3592   -0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578   -0.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680   -0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7797    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3812    0.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900    0.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8017    1.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3885   -0.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5768   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640   -2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728   -2.9699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261   -1.3761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -1.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -2.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2629   -3.4419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2140   -0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5032    0.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3958    1.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    2.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083    1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3144    0.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932    0.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078   -0.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -0.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598   -0.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3665   -1.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548   -2.0604    0.0000 O   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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  3  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    4.7606   -0.6514    2.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -0.6607    1.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166   -0.2389    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0982    1.0337    0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9544    2.1005    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828    1.4865   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171    2.7166   -0.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0584    0.4637   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.8614   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -1.2745   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -2.4787   -0.0015 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.8549   -1.4420 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8676   -3.2418   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605   -3.6610    0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -1.5031   -1.2859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8667   -2.2455   -0.6348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9735   -2.4394   -1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -2.5917   -2.3863 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102   -1.5446    0.5427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2479   -0.2869    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316    0.8988    0.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0361    0.0603    0.4990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1404   -0.1819   -1.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2178    0.8990   -1.5354 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8035    2.0883   -0.9317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    3.1386   -1.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    3.8656   -1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3746    3.2323    0.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    1.8910   -0.4404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3507   -1.0585    1.3154 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7243   -0.6600    2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0158   -1.2813    3.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8059    0.3804    2.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468   -1.1434    2.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8576    3.0234    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227    1.7769    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6678    2.3193    2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829   -1.6918   -2.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732   -3.5524   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -3.9850   -1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895   -4.5873    0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950   -3.2653   -0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -2.3114    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515   -0.1730   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160   -0.2470    1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    1.2805    1.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    0.6343    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878    0.0326   -1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296    0.9326   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    3.8798   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    2.7559   -2.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982    4.9384   -1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    3.5884   -1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187    1.8318   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7839   -0.4454    2.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1443    0.2780    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379   -1.4091    3.3807 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  3  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 30  1  0
 30 31  1  0
  9 10  1  0
 10 11  2  0
 10  3  1  0
 24  8  1  0
 23 15  1  0
 30 19  1  0
 22 21  1  0
 25 29  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
 12 38  1  6
 13 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  1
 19 43  1  1
 20 44  1  0
 20 45  1  0
 21 46  1  1
 29 54  1  6
 27 52  1  0
 27 53  1  0
 26 50  1  0
 26 51  1  0
 24 49  1  6
 23 48  1  6
 22 47  1  6
 31 55  1  0
 31 56  1  0
 31 57  1  0
M  END


  Mrv1533004251523452D          

 31 36  0  0  0  0            999 V2000
    7.3592   -0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578   -0.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680   -0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7797    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3812    0.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900    0.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8017    1.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3885   -0.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5768   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640   -2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728   -2.9699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261   -1.3761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -1.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -2.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2629   -3.4419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2140   -0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5032    0.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3958    1.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    2.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083    1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3144    0.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932    0.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078   -0.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -0.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598   -0.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3665   -1.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548   -2.0604    0.0000 O   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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  3  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0237692

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C2=C(C(CO)N3C(C#N)C4CC5C6OCCN6C2C3C5N4C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N4O5/c1-9-19(28)15-14(20(29)21(9)30-3)13(8-27)26-12(7-23)11-6-10-16(24(11)2)18(26)17(15)25-4-5-31-22(10)25/h10-13,16-18,22,27H,4-6,8H2,1-3H3

> <INCHI_KEY>
KDWXMIJUXUSUMZ-UHFFFAOYSA-N

> <FORMULA>
C22H26N4O5

> <MOLECULAR_WEIGHT>
426.473

> <EXACT_MASS>
426.190319953

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.77071752761539

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-0.2001230393333329

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.039486899950301

> <JCHEM_PKA_STRONGEST_BASIC>
5.2491069870683

> <JCHEM_POLAR_SURFACE_AREA>
106.34

> <JCHEM_REFRACTIVITY>
110.54179999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      13.737  -0.684   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.614  -1.738   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.140  -1.293   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.789   0.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.912   1.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.315   0.652   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.963   2.151   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.192  -0.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.543  -1.901   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.394  -2.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.773  -4.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.669  -5.544   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       5.835  -2.569   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.432  -3.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.328  -4.888   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.224  -6.425   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.086  -2.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.266  -0.464   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.524   0.646   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.673   1.856   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.472   3.382   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.862   4.045   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.922   2.928   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       6.187   1.574   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       6.707   0.075   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.615  -1.048   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.141  -0.620   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.538  -1.458   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       1.053  -1.052   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.017  -2.347   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.369  -3.846   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   25                                                  
CONECT    9    8   10   30                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   26                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20   25                                                  
CONECT   25   24    8   26                                                  
CONECT   26   25   13   27                                                  
CONECT   27   26   19   28                                                  
CONECT   28   27   17   29                                                  
CONECT   29   28                                                            
CONECT   30    9    3   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
Cyanonaphthyridinomycin	MeSH

Chemical Formula

C₂₂H₂₆N₄O₅

Average Mass

426.4730 Da

Monoisotopic Mass

426.19032 Da

IUPAC Name

16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile

Traditional Name

16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C(C(CO)N3C(C#N)C4CC5C6OCCN6C2C3C5N4C)C1=O

InChI Identifier

InChI=1S/C22H26N4O5/c1-9-19(28)15-14(20(29)21(9)30-3)13(8-27)26-12(7-23)11-6-10-16(24(11)2)18(26)17(15)25-4-5-31-22(10)25/h10-13,16-18,22,27H,4-6,8H2,1-3H3

InChI Key

KDWXMIJUXUSUMZ-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces flavogriseus	LOTUS Database	35616633
Streptomyces flavovirens	LOTUS Database	35616633
Streptomyces lusitanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinoline quinones

Direct Parent

Isoquinoline quinones

Alternative Parents

Substituents

Isoquinoline quinone
Isoquinolone
Diazanaphthalene
Naphthyridine
Piperazino-3,4-b-piperidine
Azepane
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
N-alkylpyrrolidine
Piperidine
Oxazolidine
Vinylogous ester
Pyrrolidine
Hemiaminal
Alpha-aminonitrile
Ketone
Tertiary aliphatic amine
Tertiary amine
Nitrile
Carbonitrile
Oxacycle
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.03	ALOGPS
logP	-0.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	15.04	ChemAxon
pKa (Strongest Basic)	5.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.54 m³·mol⁻¹	ChemAxon
Polarizability	43.77 Å³	ChemAxon
Number of Rings	6	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100158

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile (NP0237692)

MOL for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

3D MOL for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

3D SDF for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

3D-SDF for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

PDB for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

3D PDB for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

SMILES for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

INCHI for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

Structure for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)

3D Structure for NP0237692 (16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-11,14-dioxo-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]henicosa-10(15),12-diene-21-carbonitrile)