NP-MRD: Showing NP-Card for Streptophenazine B (NP0007680)

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Record Information

Version

1.0

Created at

2020-12-09 04:29:52 UTC

Updated at

2021-07-15 16:58:15 UTC

NP-MRD ID

NP0007680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Streptophenazine B

Provided By

NPAtlas

Description

Methyl 6-(3-hydroxy-1-methoxy-1-oxononan-2-yl)phenazine-1-carboxylate belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring. Streptophenazine B is found in Streptomyces sp. It was first documented in 2008 (PMID: 18396903). Based on a literature review very few articles have been published on methyl 6-(3-hydroxy-1-methoxy-1-oxononan-2-yl)phenazine-1-carboxylate (PMID: 27097765).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119023D          

 59 61  0  0  0  0            999 V2000
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    6.2749   -0.9375   -0.1847 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9937    0.5126    0.0422 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9022    0.7554    1.0265 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5610    0.1471    0.6215 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1178    0.7181   -0.6760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8332    0.2290   -1.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8485   -1.1707   -1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5794    0.6352   -0.5587 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3604    1.0821    1.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -1.1123    1.2721 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -1.4425    2.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7039   -0.7832   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
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  6  7  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242119023D          

 59 61  0  0  0  0            999 V2000
    7.4022   -1.0955   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2749   -0.9375   -0.1847 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.3077    1.5307    2.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808    0.9772    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114    0.8277    0.5209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690    0.2925   -0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3099   -1.5504   -0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5892   -0.1079   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1062   -1.7804   -2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3930   -1.5176   -0.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -1.3600    0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9069    1.0294    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7964    1.0563   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1941    0.3840    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.8609    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798    0.2718    1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7073   -0.9615    0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    1.8271   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122    0.5248   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    0.6679   -2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -1.4130   -1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.7619   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -2.5072    2.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6402   -1.1598    2.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.7810    3.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -0.5277   -3.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615   -1.2565   -4.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -1.0135   -3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5371   -0.0946   -1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9674   -1.7809   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3725   -0.8108   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6225    1.3387    2.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    2.1167    4.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    1.8568    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  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 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 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
 31 14  1  0  0  0  0
 31 18  1  0  0  0  0
 29 20  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
  2 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  4 39  1  0  0  0  0
  4 40  1  0  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  0  0  0  0
  6 44  1  0  0  0  0
  7 45  1  6  0  0  0
  8 46  1  0  0  0  0
  9 47  1  1  0  0  0
 13 48  1  0  0  0  0
 13 49  1  0  0  0  0
 13 50  1  0  0  0  0
 15 51  1  0  0  0  0
 16 52  1  0  0  0  0
 17 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 26 57  1  0  0  0  0
 27 58  1  0  0  0  0
 28 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C1=C([H])C([H])=C([H])C2=NC3=C(C([H])=C([H])C([H])=C3N=C12)C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O5/c1-4-5-6-7-14-19(27)20(24(29)31-3)15-10-8-12-17-21(15)25-18-13-9-11-16(22(18)26-17)23(28)30-2/h8-13,19-20,27H,4-7,14H2,1-3H3/t19-,20-/m1/s1

> <INCHI_KEY>
SOKLNJHTUUKGKZ-UHFFFAOYSA-N

> <FORMULA>
C24H28N2O5

> <MOLECULAR_WEIGHT>
424.497

> <EXACT_MASS>
424.19982201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.703887192643435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 6-[(2R,3R)-3-hydroxy-1-methoxy-1-oxononan-2-yl]phenazine-1-carboxylate

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
4.8269622886666665

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.507706366008534

> <JCHEM_PKA_STRONGEST_BASIC>
-0.20699837822229916

> <JCHEM_POLAR_SURFACE_AREA>
98.61000000000001

> <JCHEM_REFRACTIVITY>
114.95460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-[(2R,3R)-3-hydroxy-1-methoxy-1-oxononan-2-yl]phenazine-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    7.4022   -1.0955   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1178    0.7181   -0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4785    0.2115    0.8673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    1.0821    1.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -1.1123    1.2721 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -1.4425    2.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    0.1542   -1.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2248    0.0053   -0.7476 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3158    0.5536    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507    0.6847    1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7275    0.2257    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8518    0.3266    0.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6088   -0.3115   -0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7039   -0.7832   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6500    1.2469    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5241    1.6762    3.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077    1.5307    2.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808    0.9772    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114    0.8277    0.5209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690    0.2925   -0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3099   -1.5504   -0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5892   -0.1079   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1062   -1.7804   -2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3930   -1.5176   -0.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -1.3600    0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9069    1.0294    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7964    1.0563   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1941    0.3840    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.8609    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798    0.2718    1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7073   -0.9615    0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    1.8271   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122    0.5248   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    0.6679   -2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -1.4130   -1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.7619   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -2.5072    2.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6402   -1.1598    2.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.7810    3.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -0.5277   -3.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615   -1.2565   -4.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -1.0135   -3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5371   -0.0946   -1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9674   -1.7809   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3725   -0.8108   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6225    1.3387    2.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    2.1167    4.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    1.8568    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  2  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 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 14  1  0
 31 18  1  0
 29 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  6
  8 46  1  0
  9 47  1  1
 13 48  1  0
 13 49  1  0
 13 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       7.402  -1.095  -1.195  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.275  -0.938  -0.185  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.994   0.513   0.042  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.902   0.755   1.026  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.561   0.147   0.622  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.118   0.718  -0.676  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.833   0.229  -1.229  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.849  -1.171  -1.438  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.579   0.635  -0.559  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.479   0.212   0.867  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.360   1.082   1.798  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.504  -1.112   1.272  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.402  -1.442   2.658  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.618   0.154  -1.320  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.489  -0.393  -2.564  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.651  -0.821  -3.221  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.869  -0.673  -2.593  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.016  -0.125  -1.343  0.00  0.00           C+0
HETATM   19  N   UNK     0      -4.225   0.005  -0.748  0.00  0.00           N+0
HETATM   20  C   UNK     0      -4.316   0.554   0.494  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.551   0.685   1.101  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.728   0.226   0.385  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.852   0.327   0.925  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.609  -0.312  -0.866  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.704  -0.783  -1.632  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.650   1.247   2.379  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.524   1.676   3.047  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.308   1.531   2.413  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.181   0.977   1.148  0.00  0.00           C+0
HETATM   30  N   UNK     0      -2.011   0.828   0.521  0.00  0.00           N+0
HETATM   31  C   UNK     0      -1.869   0.293  -0.704  0.00  0.00           C+0
HETATM   32  H   UNK     0       8.310  -1.550  -0.735  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.589  -0.108  -1.648  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.106  -1.780  -2.020  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.393  -1.518  -0.466  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.665  -1.360   0.780  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.907   1.029   0.457  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.796   1.056  -0.917  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.194   0.384   2.019  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.708   1.861   1.083  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.880   0.272   1.460  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.707  -0.962   0.476  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.036   1.827  -0.535  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.912   0.525  -1.454  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.793   0.668  -2.288  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.706  -1.413  -1.910  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.486   1.762  -0.586  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.614  -2.507   2.761  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.640  -1.160   2.970  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.151  -0.781   3.169  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.432  -0.528  -3.101  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.562  -1.256  -4.210  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.763  -1.014  -3.123  0.00  0.00           H+0
HETATM   54  H   UNK     0      -8.537  -0.095  -1.500  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.967  -1.781  -1.259  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.372  -0.811  -2.698  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.622   1.339   2.833  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.604   2.117   4.050  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.407   1.857   2.909  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   35   36                                             
CONECT    3    2    4   37   38                                             
CONECT    4    3    5   39   40                                             
CONECT    5    4    6   41   42                                             
CONECT    6    5    7   43   44                                             
CONECT    7    6    8    9   45                                             
CONECT    8    7   46                                                       
CONECT    9    7   10   14   47                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   48   49   50                                             
CONECT   14    9   15   31                                                  
CONECT   15   14   16   51                                                  
CONECT   16   15   17   52                                                  
CONECT   17   16   18   53                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   54   55   56                                             
CONECT   26   21   27   57                                                  
CONECT   27   26   28   58                                                  
CONECT   28   27   29   59                                                  
CONECT   29   28   30   20                                                  
CONECT   30   29   31                                                       
CONECT   31   30   14   18                                                  
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   13                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
    7.4022   -1.0955   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2749   -0.9375   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9937    0.5126    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022    0.7554    1.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5610    0.1471    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178    0.7181   -0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332    0.2290   -1.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8485   -1.1707   -1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5794    0.6352   -0.5587 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4785    0.2115    0.8673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    1.0821    1.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -1.1123    1.2721 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -1.4425    2.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    0.1542   -1.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4887   -0.3933   -2.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3158    0.5536    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507    0.6847    1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7275    0.2257    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8518    0.3266    0.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6088   -0.3115   -0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7039   -0.7832   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6500    1.2469    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5241    1.6762    3.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077    1.5307    2.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808    0.9772    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114    0.8277    0.5209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690    0.2925   -0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3099   -1.5504   -0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5892   -0.1079   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1062   -1.7804   -2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3930   -1.5176   -0.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -1.3600    0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9069    1.0294    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7964    1.0563   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1941    0.3840    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.8609    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798    0.2718    1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7073   -0.9615    0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    1.8271   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122    0.5248   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    0.6679   -2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -1.4130   -1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.7619   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -2.5072    2.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6402   -1.1598    2.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.7810    3.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -0.5277   -3.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615   -1.2565   -4.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -1.0135   -3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5371   -0.0946   -1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9674   -1.7809   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3725   -0.8108   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6225    1.3387    2.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    2.1167    4.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073    1.8568    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  2  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 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 14  1  0
 31 18  1  0
 29 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  6
  8 46  1  0
  9 47  1  1
 13 48  1  0
 13 49  1  0
 13 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 6-(3-hydroxy-1-methoxy-1-oxononan-2-yl)phenazine-1-carboxylic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₅

Average Mass

424.4970 Da

Monoisotopic Mass

424.19982 Da

IUPAC Name

methyl 6-[(2R,3R)-3-hydroxy-1-methoxy-1-oxononan-2-yl]phenazine-1-carboxylate

Traditional Name

methyl 6-[(2R,3R)-3-hydroxy-1-methoxy-1-oxononan-2-yl]phenazine-1-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCCC(O)C(C(=O)OC)C1=CC=CC2=NC3=C(C=CC=C3N=C12)C(=O)OC

InChI Identifier

InChI=1S/C24H28N2O5/c1-4-5-6-7-14-19(27)20(24(29)31-3)15-10-8-12-17-21(15)25-18-13-9-11-16(22(18)26-17)23(28)30-2/h8-13,19-20,27H,4-7,14H2,1-3H3

InChI Key

SOKLNJHTUUKGKZ-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
Streptomyces sp.	NPAtlas	18396903

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phenazines and derivatives

Alternative Parents

Substituents

Phenazine
Beta-hydroxy acid
Fatty acid ester
Hydroxy acid
Pyrazine
Benzenoid
Fatty acyl
Methyl ester
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	4.17	ALOGPS
logP	4.83	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	-0.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	98.61 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	114.95 m³·mol⁻¹	ChemAxon
Polarizability	46.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA000726

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24693497

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24879154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mitova MI, Lang G, Wiese J, Imhoff JF: Subinhibitory concentrations of antibiotics induce phenazine production in a marine Streptomyces sp. J Nat Prod. 2008 May;71(5):824-7. doi: 10.1021/np800032a. Epub 2008 Apr 9. [PubMed:18396903 ]
Liang Y, Chen L, Ye X, Anjum K, Lian XY, Zhang Z: New streptophenazines from marine Streptomyces sp. 182SMLY. Nat Prod Res. 2017 Feb;31(4):411-417. doi: 10.1080/14786419.2016.1169419. Epub 2016 Apr 20. [PubMed:27097765 ]

Showing NP-Card for Streptophenazine B (NP0007680)

MOL for NP0007680 (Streptophenazine B)

3D MOL for NP0007680 (Streptophenazine B)

3D SDF for NP0007680 (Streptophenazine B)

3D-SDF for NP0007680 (Streptophenazine B)

PDB for NP0007680 (Streptophenazine B)

3D PDB for NP0007680 (Streptophenazine B)

SMILES for NP0007680 (Streptophenazine B)

INCHI for NP0007680 (Streptophenazine B)

Structure for NP0007680 (Streptophenazine B)

3D Structure for NP0007680 (Streptophenazine B)