NP-MRD: Showing NP-Card for (3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid (NP0177722)

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Record Information

Version

2.0

Created at

2022-09-03 15:36:05 UTC

Updated at

2022-09-03 15:36:05 UTC

NP-MRD ID

NP0177722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid

Description

(3R,4R,5R)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxo-3H-phenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. (3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid is found in Streptomyces griseus. Based on a literature review very few articles have been published on (3R,4R,5R)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxo-3H-phenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217362D          

 31 34  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -5.5473   -2.9728   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2011   -2.3461   -0.2594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -1.1020   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0339   -0.4270    0.6160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8330   -0.4361   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535    0.8809   -0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6482    1.6222    0.3837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4695    1.5905   -0.7978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1424    2.6500    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    0.7910   -1.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7399    1.1276   -2.3777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3733   -0.6915   -0.9626 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0073   -1.0348    0.3904 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728   -0.9262    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156   -0.6189   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6440   -0.5342    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180   -0.2333   -0.5298 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8748   -0.1622   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878    0.1496   -0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1785    0.2201   -0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3031    0.5453   -1.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5381    1.9166   -1.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4505   -0.0145    0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305   -0.3184    1.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387   -0.3937    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.6936    2.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9395   -0.7784    1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9212   -1.0861    2.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -1.1537    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899   -1.4363    2.9518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7679   -1.0966   -1.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -1.9730   -2.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8963   -0.2705    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5146    1.9813    1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5410    1.8096   -0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7674    2.1188   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1491    2.7230    0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    1.1258   -0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4612    1.1845   -3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.1706   -1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7307   -1.3618    1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -0.4426   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6936    0.3353   -2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2327    0.0647   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0444    0.1983   -2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4727    2.3683   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565    0.0376    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6280   -0.5056    2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1889   -1.2605    3.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  5 31  1  0
 31 32  2  0
 31 12  1  0
 12 13  1  0
 13 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  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
 29 14  1  0
 27 16  1  0
 25 18  1  0
  7 34  1  0
  7 35  1  0
  4 33  1  0
  2  1  1  0
 12 40  1  6
 13 41  1  0
 15 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 28 49  1  0
 10 38  1  1
 11 39  1  0
  8 36  1  6
  9 37  1  0
M  END


  Mrv1652309032217362D          

 31 34  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0177722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(C(O)=N)C(=O)[C@H](NC2=CC3=NC4=CC(CO)=CC=C4OC3=CC2=O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18N4O7/c21-15-14(20(22)30)17(27)16(19(29)18(15)28)24-8-4-10-13(5-11(8)26)31-12-2-1-7(6-25)3-9(12)23-10/h1-5,16,18-19,24-25,28-29H,6,21H2,(H2,22,30)/t16-,18+,19+/m0/s1

> <INCHI_KEY>
NURWOUVTSOIROK-QXAKKESOSA-N

> <FORMULA>
C20H18N4O7

> <MOLECULAR_WEIGHT>
426.385

> <EXACT_MASS>
426.117548936

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
41.3568696525244

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5R)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxo-3H-phenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid

> <JCHEM_LOGP>
-4.354441680921058

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.92601443160258

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8867121022464595

> <JCHEM_PKA_STRONGEST_BASIC>
11.575247938164619

> <JCHEM_POLAR_SURFACE_AREA>
198.54999999999995

> <JCHEM_REFRACTIVITY>
122.68259999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,5R)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   30                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   15   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   13   29                                                  
CONECT   29   28                                                            
CONECT   30   11    4   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(3R,4R,5R)-2-Amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxo-3H-phenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidate	Generator

Chemical Formula

C₂₀H₁₈N₄O₇

Average Mass

426.3850 Da

Monoisotopic Mass

426.11755 Da

IUPAC Name

(3R,4R,5R)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxo-3H-phenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid

Traditional Name

(3R,4R,5R)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid

CAS Registry Number

Not Available

SMILES

NC1=C(C(O)=N)C(=O)[C@H](NC2=CC3=NC4=CC(CO)=CC=C4OC3=CC2=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H18N4O7/c21-15-14(20(22)30)17(27)16(19(29)18(15)28)24-8-4-10-13(5-11(8)26)31-12-2-1-7(6-25)3-9(12)23-10/h1-5,16,18-19,24-25,28-29H,6,21H2,(H2,22,30)/t16-,18+,19+/m0/s1

InChI Key

NURWOUVTSOIROK-QXAKKESOSA-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 griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Phenoxazines

Direct Parent

Phenoxazines

Alternative Parents

Substituents

Phenoxazine
Secondary aliphatic/aromatic amine
Cyclohexenone
Benzenoid
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Ketone
Primary carboxylic acid amide
Secondary alcohol
Cyclic ketone
Secondary amine
Oxacycle
Azacycle
Carboxylic acid derivative
Enamine
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Alcohol
Primary amine
Aromatic alcohol
Amine
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	-4.4	ChemAxon
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	11.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	198.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.68 m³·mol⁻¹	ChemAxon
Polarizability	41.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

25050445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46939682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid (NP0177722)

MOL for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

3D MOL for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

3D SDF for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

3D-SDF for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

PDB for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

3D PDB for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

SMILES for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

INCHI for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

Structure for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)

3D Structure for NP0177722 ((3r,4r,5r)-2-amino-3,4-dihydroxy-5-{[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]amino}-6-oxocyclohex-1-ene-1-carboximidic acid)