NP-MRD: Showing NP-Card for 7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid (NP0184349)

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Record Information

Version

2.0

Created at

2022-09-03 23:27:06 UTC

Updated at

2022-09-03 23:27:06 UTC

NP-MRD ID

NP0184349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid

Description

21,25-Dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]Hexacosa-1(26),2,4(9),5,7,14,17(22),18,20,24-decaene-6-carboximidic acid belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. 7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid is found in Streptomyces murayamaensis. 21,25-Dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]Hexacosa-1(26),2,4(9),5,7,14,17(22),18,20,24-decaene-6-carboximidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521402D          

 35 40  0  0  0  0            999 V2000
    2.5854    2.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3649    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6768    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6122   -0.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681   -1.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0154   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6391   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4186   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5745   -1.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0423    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1068    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7036    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5477    1.7627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2736   -0.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8704   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124   -0.3976    0.0000 N   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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 11 23  2  0  0  0  0
  7 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 51 56  0  0  0  0  0  0  0  0999 V2000
   -1.1788   -2.6187    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4351   -1.8443   -0.1192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4233   -2.3333   -1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -1.3163   -1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -1.2718   -2.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095   -0.3566   -0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0289    0.1431    0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1954    1.0818    1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823    1.5340    1.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    2.4865    2.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    1.0509    0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.0812   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -0.4415   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2426   -1.2893   -1.8225 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7212    0.0571   -0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7784   -0.4115   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0724    0.0284   -1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3228    0.9682   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2624    1.4623    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672    2.3910    1.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567    1.0099    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8713    1.5291    1.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0294    2.3875    1.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606   -0.3899    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    0.4228    0.1973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6618   -0.0601   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716    0.7452   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0428    0.3235   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1879    1.2300   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9740    2.5816   -0.0805 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3296    0.8433   -0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1862   -1.0144   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0946   -1.8620   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -1.3862   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7291   -2.2460   -0.4844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -3.5848    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4683   -2.0361    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -2.7867    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -2.5496   -2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -3.2821   -0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625    1.4305    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    2.8569    3.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5703   -1.1608   -2.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8698   -0.3867   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3275    1.3204   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1234    2.9206    2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6263    1.7857    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1750    3.3019   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356    2.9105    0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1916   -1.3513   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2230   -2.9038   -1.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 24  2  1  0
 34 26  1  0
 35  2  1  0
 12  6  1  0
 21 15  1  0
 22 11  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  8 41  1  0
 10 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 27 47  1  0
 32 50  1  0
 33 51  1  0
 30 48  1  0
 30 49  1  0
M  END


  Mrv1533004231521402D          

 35 40  0  0  0  0            999 V2000
    2.5854    2.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3649    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6768    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6122   -0.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681   -1.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0154   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6391   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4186   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5745   -1.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0423    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1068    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7036    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5477    1.7627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2736   -0.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8704   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124   -0.3976    0.0000 N   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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 11 23  2  0  0  0  0
  7 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(=O)C3=C(C=C(O)C4=C3C(=O)C3=CC=CC(O)=C3C4=O)C1=NC1=CC(=CC=C1O2)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H16N2O7/c1-26-9-16(31)18-12(24(26)28-13-7-10(25(27)34)5-6-17(13)35-26)8-15(30)20-21(18)22(32)11-3-2-4-14(29)19(11)23(20)33/h2-8,29-30H,9H2,1H3,(H2,27,34)

> <INCHI_KEY>
RWSOSPPPYKHFRJ-UHFFFAOYSA-N

> <FORMULA>
C26H16N2O7

> <MOLECULAR_WEIGHT>
468.421

> <EXACT_MASS>
468.095750863

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
47.404557447754726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
21,25-dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]hexacosa-1(14),2,4,6,8,15(24),17,19,21,25-decaene-6-carboxamide

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.8659910206666663

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.33365480560935

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.311974565204103

> <JCHEM_PKA_STRONGEST_BASIC>
-0.28772227821026275

> <JCHEM_POLAR_SURFACE_AREA>
156.35

> <JCHEM_REFRACTIVITY>
126.24539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
21,25-dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]hexacosa-1(14),2,4,6,8,15(24),17,19,21,25-decaene-6-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       4.826   3.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.117   2.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.281   3.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.736   2.786   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.901   3.794   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.027   1.274   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.863   0.266   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.154  -1.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.609  -1.750   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.901  -3.263   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.774  -0.742   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.229  -1.246   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.520  -2.759   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.393  -0.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.848  -0.742   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.139  -2.254   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.012   0.266   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.721   1.778   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.266   2.282   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.102   1.274   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.647   1.778   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.356   3.290   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.483   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.408   0.770   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       4.244  -0.238   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       2.789   0.266   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.625  -0.742   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.170  -0.238   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.121   1.274   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.043   2.282   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.498   1.778   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.662   2.786   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.995  -1.246   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.704  -2.759   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0      -2.450  -0.742   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   24   32                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   23                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    6   11                                                  
CONECT   24    7    2   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31    2                                                       
CONECT   33   28   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
21,25-Dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0,.0,.0,.0,]hexacosa-1(26),2,4(9),5,7,14,17(22),18,20,24-decaene-6-carboximidate	Generator
21,25-Dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]hexacosa-1(26),2,4(9),5,7,14,17(22),18,20,24-decaene-6-carboximidate	Generator

Chemical Formula

C₂₆H₁₆N₂O₇

Average Mass

468.4210 Da

Monoisotopic Mass

468.09575 Da

IUPAC Name

21,25-dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]hexacosa-1(14),2,4,6,8,15(24),17,19,21,25-decaene-6-carboxamide

Traditional Name

21,25-dihydroxy-11-methyl-13,16,23-trioxo-10-oxa-3-azahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁷,²²]hexacosa-1(14),2,4,6,8,15(24),17,19,21,25-decaene-6-carboxamide

CAS Registry Number

Not Available

SMILES

CC12CC(=O)C3=C(C=C(O)C4=C3C(=O)C3=CC=CC(O)=C3C4=O)C1=NC1=CC(=CC=C1O2)C(N)=O

InChI Identifier

InChI=1S/C26H16N2O7/c1-26-9-16(31)18-12(24(26)28-13-7-10(25(27)34)5-6-17(13)35-26)8-15(30)20-21(18)22(32)11-3-2-4-14(29)19(11)23(20)33/h2-8,29-30H,9H2,1H3,(H2,27,34)

InChI Key

RWSOSPPPYKHFRJ-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 murayamaensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
Anthraquinone
9,10-anthraquinone
Phenanthrol
Phenanthrene
Phenoxazine
Anthracene
Benzoxazine
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Carboxamide group
Ketimine
Ketone
Primary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Imine
Organic oxide
Organonitrogen compound
Organooxygen 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	3.84	ALOGPS
logP	3.87	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	5.31	ChemAxon
pKa (Strongest Basic)	-0.29	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.35 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.25 m³·mol⁻¹	ChemAxon
Polarizability	47.4 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid (NP0184349)

MOL for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

3D MOL for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

3D SDF for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

3D-SDF for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

PDB for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

3D PDB for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

SMILES for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

INCHI for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

Structure for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)

3D Structure for NP0184349 (7,9-dihydroxy-15a-methyl-8,13,14-trioxo-15h-anthra[2,1-a]phenoxazine-3-carboximidic acid)