NP-MRD: Showing NP-Card for (2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate (NP0291538)

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Record Information

Version

2.0

Created at

2022-09-09 22:40:32 UTC

Updated at

2022-09-09 22:40:32 UTC

NP-MRD ID

NP0291538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate

Description

2'-O-L-quinovosyl saphenate 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. It was first documented in 2003 (PMID: 14527145). Based on a literature review a significant number of articles have been published on 2'-O-L-quinovosyl saphenate (PMID: 36115695) (PMID: 36115694) (PMID: 36115693) (PMID: 12538002).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200402D          

 30 33  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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
    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   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
    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 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 11 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
 10 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  4 30  2  0  0  0  0
  8 30  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    6.4858   -0.6565    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563   -0.7544   -0.7757 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6982    0.4754   -0.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3402    0.5613   -0.8087 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9568    1.8914   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528   -0.2319    0.4133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5533    0.1136    0.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445    0.6240    2.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915    0.7685    2.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1173    0.9902    2.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    1.4965    3.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515    1.8524    4.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469    1.6715    3.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    1.1657    1.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4406    0.9987    0.9300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138    0.5054   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2757    0.3487   -1.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592    0.7280   -0.8004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5631    0.5281   -1.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0686   -0.0838    0.2536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0096   -0.1567   -2.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7112   -0.5026   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6749   -0.3446   -1.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9211    0.1651   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    0.3229    0.2556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407    0.8222    1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -1.6744   -0.0119 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5703   -2.5575    0.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4563   -1.8978   -0.3198 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5094   -2.9076   -1.3125 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0454   -0.4890    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0393   -1.5923    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0860    0.2366   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7097   -0.9371   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    0.1050   -1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    2.2638   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0565    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086    1.6463    4.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632    2.2584    5.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6806    1.9350    3.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6950    1.8051   -0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2287    1.1203   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5900    0.9000   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6178   -0.5458   -2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0587   -0.0841    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8027   -0.2929   -3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611   -0.8986   -3.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.6112   -2.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4202   -1.8698   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -3.2529    0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8977   -2.4146    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959   -3.4874   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 29  1  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 10 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 17  1  0
 24 16  1  0
 26 14  1  0
 27  6  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  1
 20 45  1  0
 13 40  1  0
 12 39  1  0
 11 38  1  0
  6 37  1  1
  4 35  1  6
  5 36  1  0
  2 34  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
 29 51  1  1
 30 52  1  0
 27 49  1  6
 28 50  1  0
 23 48  1  0
 22 47  1  0
 21 46  1  0
M  END


  Mrv1652309102200402D          

 30 33  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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
    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   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
    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 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 11 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
 10 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  4 30  2  0  0  0  0
  8 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C1=C2N=C3C=CC=C(C(=O)O[C@@H]4[C@@H](O)O[C@@H](C)[C@H](O)[C@H]4O)C3=NC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O7/c1-9(24)11-5-3-7-13-15(11)22-14-8-4-6-12(16(14)23-13)20(27)30-19-18(26)17(25)10(2)29-21(19)28/h3-10,17-19,21,24-26,28H,1-2H3/t9?,10-,17-,18+,19-,21-/m0/s1

> <INCHI_KEY>
OZPGCLJPZPDKKZ-XNZNGCIUSA-N

> <FORMULA>
C21H22N2O7

> <MOLECULAR_WEIGHT>
414.414

> <EXACT_MASS>
414.142701056

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.2574183777575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4R,5R,6S)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate

> <JCHEM_LOGP>
1.3459058166666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.816593684147826

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.305779588218549

> <JCHEM_PKA_STRONGEST_BASIC>
-0.35536008504597383

> <JCHEM_POLAR_SURFACE_AREA>
142.23000000000002

> <JCHEM_REFRACTIVITY>
102.53499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R,6S)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15   24                                                  
CONECT   24   23                                                            
CONECT   25   11   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   10   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
2'-O-L-Quinovosyl saphenic acid	Generator

Chemical Formula

C₂₁H₂₂N₂O₇

Average Mass

414.4140 Da

Monoisotopic Mass

414.14270 Da

IUPAC Name

(2S,3S,4R,5R,6S)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate

Traditional Name

(2S,3S,4R,5R,6S)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC(O)C1=C2N=C3C=CC=C(C(=O)O[C@@H]4[C@@H](O)O[C@@H](C)[C@H](O)[C@H]4O)C3=NC2=CC=C1

InChI Identifier

InChI=1S/C21H22N2O7/c1-9(24)11-5-3-7-13-15(11)22-14-8-4-6-12(16(14)23-13)20(27)30-19-18(26)17(25)10(2)29-21(19)28/h3-10,17-19,21,24-26,28H,1-2H3/t9?,10-,17-,18+,19-,21-/m0/s1

InChI Key

OZPGCLJPZPDKKZ-XNZNGCIUSA-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

Not Available

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
Hexose monosaccharide
Monosaccharide
Oxane
Benzenoid
Pyrazine
Heteroaromatic compound
1,2-diol
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Azacycle
Polyol
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
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	1.35	ChemAxon
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-0.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.54 m³·mol⁻¹	ChemAxon
Polarizability	42.26 Å³	ChemAxon
Number of Rings	4	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

10249723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15109444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

eBioMedicine: The dynamics of the immune system and gut in the pathophysiology of multiple sclerosis. EBioMedicine. 2022 Sep;83:104273. doi: 10.1016/j.ebiom.2022.104273. [PubMed:36115695 ]
Lundgren S, Keranen M, Wartiovaara-Kautto U, Myllymaki M: Somatic compensation of inherited bone marrow failure. Semin Hematol. 2022 Jul;59(3):167-173. doi: 10.1053/j.seminhematol.2022.07.002. Epub 2022 Aug 3. [PubMed:36115694 ]
Alcedo PE, Gutierrez-Rodrigues F, Patel BA: Somatic mutations in VEXAS Syndrome and Erdheim-Chester disease: Inflammatory myeloid diseases. Semin Hematol. 2022 Jul;59(3):156-166. doi: 10.1053/j.seminhematol.2022.07.003. Epub 2022 Aug 3. [PubMed:36115693 ]
Laursen JB, Petersen L, Jensen KJ, Nielsen J: Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors. Org Biomol Chem. 2003 Sep 21;1(18):3147-53. doi: 10.1039/b306789k. [PubMed:14527145 ]
Laursen JB, Jorgensen CG, Nielsen J: First synthesis of racemic saphenamycin and its enantiomers. investigation of biological activity. Bioorg Med Chem. 2003 Mar 6;11(5):723-31. doi: 10.1016/s0968-0896(02)00472-8. [PubMed:12538002 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate (NP0291538)

MOL for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

3D MOL for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

3D SDF for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

3D-SDF for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

PDB for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

3D PDB for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

SMILES for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

INCHI for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

Structure for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)

3D Structure for NP0291538 ((2s,3s,4r,5r,6s)-2,4,5-trihydroxy-6-methyloxan-3-yl 6-(1-hydroxyethyl)phenazine-1-carboxylate)