NP-MRD: Showing NP-Card for questiomycin A (NP0025057)

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Record Information

Version

1.0

Created at

2021-06-19 17:16:31 UTC

Updated at

2021-08-20 00:00:07 UTC

NP-MRD ID

NP0025057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

questiomycin A

Provided By

JEOL Database JEOL Logo

Description

Questiomycin A, also known as isophenoxazine or 2-aminophenoxazon, 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. Questiomycin A is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. questiomycin A is found in Calocybe gambosa , Leucoagaricus americanus, Streptomyces griseus Acta 2871 and Streptomyces thioluteus. It was first documented in 2012 (PMID: 23113707). Based on a literature review very few articles have been published on Questiomycin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119163D          

 24 26  0  0  0  0            999 V2000
    4.6184    3.2669   -1.2666 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2756    3.0598   -1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    2.0791   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282    1.8870   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5221    0.9112   -0.4764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552    0.7862   -0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5607   -0.2459   -0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -0.4046   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    0.4716   -1.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    1.5071   -1.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470    1.6599   -1.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180    2.6992   -2.2236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    2.8432   -1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216    3.8279   -2.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5640    4.0153   -2.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625    4.9314   -2.9222 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1768    2.6748   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0404    4.0486   -1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    1.3689   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -0.9295    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4686   -1.2127    0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6741    0.3469   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4397    2.1909   -2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    4.5329   -3.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 11  6  2  0  0  0  0
  4 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
  6  7  1  0  0  0  0
 14 15  1  0  0  0  0
 12 13  1  0  0  0  0
 15  2  1  0  0  0  0
  7  8  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 15 16  2  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
  7 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 14 24  1  0  0  0  0
  3 19  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C1=C([H])C2=NC3=C(OC2=C([H])C1=O)C([H])=C([H])C([H])=C3[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H8N2O2/c13-7-5-9-12(6-10(7)15)16-11-4-2-1-3-8(11)14-9/h1-6H,13H2

> <INCHI_KEY>
RDJXPXHQENRCNG-UHFFFAOYSA-N

> <FORMULA>
C12H8N2O2

> <MOLECULAR_WEIGHT>
212.2041

> <EXACT_MASS>
212.05857751

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
21.363998240399344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-3H-phenoxazin-3-one

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
1.193749461

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.951691158998358

> <JCHEM_PKA_STRONGEST_BASIC>
-0.29320707843769134

> <JCHEM_POLAR_SURFACE_AREA>
64.67999999999999

> <JCHEM_REFRACTIVITY>
63.56860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminophenoxazin-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  N   UNK     0       4.618   3.267  -1.267  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.276   3.060  -1.445  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.578   2.079  -0.862  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.128   1.887  -1.079  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.522   0.911  -0.476  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.855   0.786  -0.727  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.561  -0.246  -0.106  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.931  -0.405  -0.329  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.608   0.472  -1.178  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.916   1.507  -1.805  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.547   1.660  -1.578  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.918   2.699  -2.224  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.442   2.843  -1.992  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.122   3.828  -2.583  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.564   4.015  -2.364  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.163   4.931  -2.922  0.00  0.00           O+0
HETATM   17  H   UNK     0       5.177   2.675  -0.668  0.00  0.00           H+0
HETATM   18  H   UNK     0       5.040   4.049  -1.765  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.050   1.369  -0.193  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.035  -0.930   0.556  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.469  -1.213   0.161  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.674   0.347  -1.350  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.440   2.191  -2.466  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.642   4.533  -3.250  0.00  0.00           H+0
CONECT    1    2   17   18                                                  
CONECT    2   15    3    1                                                  
CONECT    3    2    4   19                                                  
CONECT    4   13    3    5                                                  
CONECT    5    6    4                                                       
CONECT    6    5   11    7                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   21                                                  
CONECT    9   10    8   22                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13    4   14   12                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Isophenoxazine	ChEBI
3-Aminophenoxazone	Kegg
2-Amino-3-phenoxazone	HMDB
2-Amino-3H-phenoxazin-3-one	HMDB
2-Amino-phenoxazin-3-one	HMDB
2-Aminophenoxazin-3-one	HMDB
2-Aminophenoxazon	HMDB
2-Aminophenoxazone	HMDB
Acrospermum viticola toxin C	HMDB
AV toxin C	HMDB
NSC 94945	HMDB
PHX-3 CPD	HMDB
2-Acetylamino-(3H)-phenoxazin-3-one	HMDB
2-Aminophenoxazine-3-one	HMDB
Questinomycine a	HMDB
Questiomycin a	ChEBI
Questiomycin A	HMDB

Chemical Formula

C₁₂H₈N₂O₂

Average Mass

212.2041 Da

Monoisotopic Mass

212.05858 Da

IUPAC Name

2-amino-3H-phenoxazin-3-one

Traditional Name

2-aminophenoxazin-3-one

CAS Registry Number

Not Available

SMILES

[H]N([H])C1=C([H])C2=NC3=C(OC2=C([H])C1=O)C([H])=C([H])C([H])=C3[H]

InChI Identifier

InChI=1S/C12H8N2O2/c13-7-5-9-12(6-10(7)15)16-11-4-2-1-3-8(11)14-9/h1-6H,13H2

InChI Key

RDJXPXHQENRCNG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calocybe gambosa	-	KNApSAcK
Leucoagaricus americanus	LOTUS Database	35616633
Streptomyces griseus Acta 2871	JEOL database	Graf, E., et al, J. Antibiot. 60, 277 (2007)
Streptomyces thioluteus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces sp.	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

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	40350 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.06	ALOGPS
logP	1.19	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	19.95	ChemAxon
pKa (Strongest Basic)	-0.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.68 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.57 m³·mol⁻¹	ChemAxon
Polarizability	21.36 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	No	ChemAxon

External Links

HMDB ID

HMDB0030483

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Questiomycin A

METLIN ID

Not Available

PubChem Compound

72725

PDB ID

Not Available

ChEBI ID

17293

Good Scents ID

rw1820341

References

General References

Adhikari KB, Laerke HN, Mortensen AG, Fomsgaard IS: Plasma and urine concentrations of bioactive dietary benzoxazinoids and their glucuronidated conjugates in rats fed a rye bread-based diet. J Agric Food Chem. 2012 Nov 21;60(46):11518-24. doi: 10.1021/jf301737n. Epub 2012 Nov 12. [PubMed:23113707 ]
Graf, E., et al. (2007). Graf, E., et al, J. Antibiot. 60, 277 (2007). J. Antibiotics.

Showing NP-Card for questiomycin A (NP0025057)

MOL for NP0025057 (questiomycin A)

3D MOL for NP0025057 (questiomycin A)

3D SDF for NP0025057 (questiomycin A)

3D-SDF for NP0025057 (questiomycin A)

PDB for NP0025057 (questiomycin A)

3D PDB for NP0025057 (questiomycin A)

SMILES for NP0025057 (questiomycin A)

INCHI for NP0025057 (questiomycin A)

Structure for NP0025057 (questiomycin A)

3D Structure for NP0025057 (questiomycin A)