NP-MRD: Showing NP-Card for [(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid (NP0306778)

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Record Information

Version

2.0

Created at

2022-09-10 23:28:37 UTC

Updated at

2022-09-10 23:28:37 UTC

NP-MRD ID

NP0306778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid

Description

{[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]Trideca-1(9),11-dien-8-yl]methoxy}carboximidic acid belongs to the class of organic compounds known as mitomycins, mitosane and mitosene derivatives. These are a group of pyrroloindolediones, which carry a methyl group at the 6-position of their quinone moiety. The mitosane (containing an aziridine) and mitosene server as backbone for mitomycins and their derivatives. [(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid is found in Streptomyces caespitosus. Based on a literature review very few articles have been published on {[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]Trideca-1(9),11-dien-8-yl]methoxy}carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201282D          

 25 28  0  0  1  0            999 V2000
   -1.4674    0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8593   -0.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017    1.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    2.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5014    0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -0.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -1.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333   -0.5639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1122   -1.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628   -1.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9416   -2.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -2.8910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2699   -3.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6513   -0.0174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9801   -0.7741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726    0.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    1.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    0.7392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594    0.3093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0648    0.1305    0.0000 C   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
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 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
  8 23  1  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    1.8351    3.9394   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167    4.5071   -0.3492 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    4.0855    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2726    5.0619    1.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4761    2.7486    0.9133 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923    1.7997    0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    0.3548    0.4937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5238    0.0616    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5656   -1.0885   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555   -1.5475   -1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9019   -2.6280   -1.7094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757   -0.8166   -0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3847   -1.3361   -1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0112    0.2922   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033    0.9547    0.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620    1.0498    1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    0.7875    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565    1.8402    1.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6984   -1.6473   -0.7069 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -2.7275   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4187   -2.4659    0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8956   -1.0919   -0.2453 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5374   -1.8271    0.6931 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913   -2.1874    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209   -0.5068   -0.4893 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5478    0.1950   -1.7217 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0176    5.6194    1.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    2.0416   -0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    2.0095    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0831    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2026   -2.0874   -2.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -1.8256   -0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9350   -0.4690   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143    1.5773    2.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0883    0.0867    1.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6469    1.7168    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -2.5857   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490   -3.7257   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6957   -2.4067    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658   -1.2279   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0712   -3.0549    1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4914   -1.3483    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136   -2.4639   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096    0.2532   -2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  7 25  1  0
 25 26  1  6
 25 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 21 23  1  0
 23 24  1  0
  8 17  1  0
 17 18  2  0
 17 14  1  0
 19  9  1  0
 19 25  1  0
 23 22  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
  7 30  1  1
  6 28  1  0
  6 29  1  0
  4 27  1  0
  2  1  1  0
 26 44  1  0
 22 40  1  6
 21 39  1  1
 20 37  1  0
 20 38  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END


  Mrv1652309112201282D          

 25 28  0  0  1  0            999 V2000
   -1.4674    0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8593   -0.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017    1.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    2.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5014    0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -0.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -1.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333   -0.5639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1122   -1.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628   -1.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9416   -2.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -2.8910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2699   -3.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6513   -0.0174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9801   -0.7741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726    0.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    1.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    0.7392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594    0.3093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0648    0.1305    0.0000 C   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
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 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
  8 23  1  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C2=C([C@H](COC(O)=N)[C@@]3(O)C4C(CN23)N4C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3O6/c1-6-11(20)10-9(12(21)13(6)24-3)7(5-25-15(17)22)16(23)14-8(18(14)2)4-19(10)16/h7-8,14,23H,4-5H2,1-3H3,(H2,17,22)/t7-,8?,14?,16+,18?/m0/s1

> <INCHI_KEY>
UZUUQCBCWDBYCG-XSHKPOLQSA-N

> <FORMULA>
C16H19N3O6

> <MOLECULAR_WEIGHT>
349.343

> <EXACT_MASS>
349.127385344

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.87833126641956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methoxy}carboximidic acid

> <JCHEM_LOGP>
-4.132912347578505

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.1499472633785528

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.196566300203348

> <JCHEM_PKA_STRONGEST_BASIC>
10.77384044434097

> <JCHEM_POLAR_SURFACE_AREA>
123.16000000000003

> <JCHEM_REFRACTIVITY>
98.11159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.739   0.885   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.604  -0.155   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.135   0.307   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.199   1.811   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.937   2.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.667   2.273   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.001   3.777   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.803   1.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.469  -0.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.000  -0.733   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.666  -2.237   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.796  -1.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.943  -2.586   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.344  -3.225   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.491  -4.758   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.892  -5.397   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       4.237  -5.652   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.949  -0.033   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.563  -1.445   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.482   0.115   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.816   1.618   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.489   2.400   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       4.335   1.380   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       7.951   0.577   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       9.454   0.244   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   23                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22    8   18                                                  
CONECT   24   21   20   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
{[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0,.0,]trideca-1(9),11-dien-8-yl]methoxy}carboximidate	Generator

Chemical Formula

C₁₆H₁₉N₃O₆

Average Mass

349.3430 Da

Monoisotopic Mass

349.12739 Da

IUPAC Name

{[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methoxy}carboximidic acid

Traditional Name

[(7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C([C@H](COC(O)=N)[C@@]3(O)C4C(CN23)N4C)C1=O

InChI Identifier

InChI=1S/C16H19N3O6/c1-6-11(20)10-9(12(21)13(6)24-3)7(5-25-15(17)22)16(23)14-8(18(14)2)4-19(10)16/h7-8,14,23H,4-5H2,1-3H3,(H2,17,22)/t7-,8?,14?,16+,18?/m0/s1

InChI Key

UZUUQCBCWDBYCG-XSHKPOLQSA-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 caespitosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as mitomycins, mitosane and mitosene derivatives. These are a group of pyrroloindolediones, which carry a methyl group at the 6-position of their quinone moiety. The mitosane (containing an aziridine) and mitosene server as backbone for mitomycins and their derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolequinones

Direct Parent

Mitomycins, mitosane and mitosene derivatives

Alternative Parents

Substituents

Mitosane core
Indole
Quinone
Pyrrolizine
N-alkylpiperazine
N-methylpiperazine
Piperazine
1,4-diazinane
Vinylogous ester
Vinylogous amide
Pyrroline
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Carboximidic acid derivative
Aziridine
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Amine
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	-4.1	ChemAxon
pKa (Strongest Acidic)	-4.2	ChemAxon
pKa (Strongest Basic)	10.77	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.11 m³·mol⁻¹	ChemAxon
Polarizability	34.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

162928581

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid (NP0306778)

MOL for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

3D MOL for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

3D SDF for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

3D-SDF for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

PDB for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

3D PDB for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

SMILES for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

INCHI for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

Structure for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)

3D Structure for NP0306778 ([(7r,8r)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methoxycarboximidic acid)