NP-MRD: Showing NP-Card for griseolutein a (NP0152270)

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Record Information

Version

2.0

Created at

2022-09-02 08:42:34 UTC

Updated at

2022-09-02 08:42:34 UTC

NP-MRD ID

NP0152270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

griseolutein a

Description

6-{[(2-Hydroxyacetyl)oxy]methyl}-9-methoxyphenazine-1-carboxylic acid 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. griseolutein a is found in Streptomyces griseoluteus. 6-{[(2-Hydroxyacetyl)oxy]methyl}-9-methoxyphenazine-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.8648    3.6375   -1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053    2.3304   -1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    1.7000   -0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3881    2.3112   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4484    1.6318    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    0.3448    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562   -0.4431    1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897    0.1602    1.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4379    0.5585    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637    0.3480   -0.8584 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7495    1.2135    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4279    1.5183   -0.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598   -0.2848    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787   -1.5413    0.8339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -2.1568    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218   -3.4690    1.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6545   -4.0527    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7131   -3.4074    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486   -2.1211   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6471   -1.3834   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7416   -1.9559   -0.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736   -0.0858   -1.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -1.4882    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748   -0.2281   -0.3685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893    0.3926   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1847    4.3119   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563    4.1134   -1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4786    3.5731   -2.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592    3.3254   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3946    2.1287    0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768   -1.4544    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9552   -0.6246    2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5806    2.1017    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    0.5074    1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    0.6702   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773   -3.9460    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073   -5.0640    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6837   -3.8961    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228    0.7242   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 25  2  0
 25 24  1  0
 24 23  2  0
 23 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 15 14  2  0
 14 13  1  0
 13  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
 13 25  1  0
 19 23  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 22 39  1  0
  7 31  1  0
  7 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
  5 30  1  0
  4 29  1  0
M  END


  Mrv1533004171522032D          

 25 27  0  0  0  0            999 V2000
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   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
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  2  0  0  0  0
 13 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
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
  3 25  2  0  0  0  0
 13 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152270

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2N=C3C(C=CC=C3C(O)=O)=NC2=C(COC(=O)CO)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O6/c1-24-12-6-5-9(8-25-13(21)7-20)14-16(12)19-15-10(17(22)23)3-2-4-11(15)18-14/h2-6,20H,7-8H2,1H3,(H,22,23)

> <INCHI_KEY>
LRNVPBRAXOLPTF-UHFFFAOYSA-N

> <FORMULA>
C17H14N2O6

> <MOLECULAR_WEIGHT>
342.307

> <EXACT_MASS>
342.085186179

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.87070167043463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{[(2-hydroxyacetyl)oxy]methyl}-9-methoxyphenazine-1-carboxylic acid

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
1.4166950173333333

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.126583370794588

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.676191576199225

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0924222447279233

> <JCHEM_POLAR_SURFACE_AREA>
118.84

> <JCHEM_REFRACTIVITY>
84.5456

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
griseolutein A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   15   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    3   13                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
6-{[(2-hydroxyacetyl)oxy]methyl}-9-methoxyphenazine-1-carboxylate	Generator

Chemical Formula

C₁₇H₁₄N₂O₆

Average Mass

342.3070 Da

Monoisotopic Mass

342.08519 Da

IUPAC Name

6-{[(2-hydroxyacetyl)oxy]methyl}-9-methoxyphenazine-1-carboxylic acid

Traditional Name

griseolutein A

CAS Registry Number

Not Available

SMILES

COC1=C2N=C3C(C=CC=C3C(O)=O)=NC2=C(COC(=O)CO)C=C1

InChI Identifier

InChI=1S/C17H14N2O6/c1-24-12-6-5-9(8-25-13(21)7-20)14-16(12)19-15-10(17(22)23)3-2-4-11(15)18-14/h2-6,20H,7-8H2,1H3,(H,22,23)

InChI Key

LRNVPBRAXOLPTF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces griseoluteus	LOTUS Database	35616633

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
Anisole
Alkyl aryl ether
Dicarboxylic acid or derivatives
Pyrazine
Benzenoid
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Ether
Azacycle
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
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	1.36	ALOGPS
logP	1.42	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.55 m³·mol⁻¹	ChemAxon
Polarizability	33.87 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

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

196985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for griseolutein a (NP0152270)

MOL for NP0152270 (griseolutein a)

3D MOL for NP0152270 (griseolutein a)

3D SDF for NP0152270 (griseolutein a)

3D-SDF for NP0152270 (griseolutein a)

PDB for NP0152270 (griseolutein a)

3D PDB for NP0152270 (griseolutein a)

SMILES for NP0152270 (griseolutein a)

INCHI for NP0152270 (griseolutein a)

Structure for NP0152270 (griseolutein a)

3D Structure for NP0152270 (griseolutein a)