MiMeDB: Showing metabocard for Grixazone A (MMDBc0015224)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:06:16 UTC

Update Date

2022-08-31 06:38:53 UTC

Metabolite ID

MMDBc0015224

Metabolite Identification

Common Name

Grixazone A

Description

grixazone A 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. grixazone A is an extremely weak basic (essentially neutral) compound (based on its pKa). A cysteine derivative that is the S-(2-amino-8-formyl-3-oxo-3H-phenoxazin-1-yl) derivative of N-acetyl-L-cysteine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108062D          

 29 31  0  0  1  0            999 V2000
   -2.1434    5.3625    0.0000 C   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
    4.2868    2.4750    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    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
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   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
   -0.7145    3.7125    0.0000 C   0  0  1  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
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    1.4289    4.1250    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    5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 N   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
   -0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  1  1  4  0  0  0
  9  2  1  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 13  3  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  8  2  0  0  0  0
 11 20  1  6  0  0  0
 21 10  1  0  0  0  0
 21 16  2  0  0  0  0
 22  6  2  0  0  0  0
 23  8  1  0  0  0  0
 24 12  2  0  0  0  0
 25 18  2  0  0  0  0
 26 18  1  0  0  0  0
 27 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28  7  1  0  0  0  0
 28 17  1  0  0  0  0
 11 29  1  6  0  0  0
M  END


  Mrv1652305152108062D          

 29 31  0  0  1  0            999 V2000
   -2.1434    5.3625    0.0000 C   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
    4.2868    2.4750    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    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
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   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
   -0.7145    3.7125    0.0000 C   0  0  1  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
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    1.4289    4.1250    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    5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 N   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
   -0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  1  1  4  0  0  0
  9  2  1  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 13  3  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  8  2  0  0  0  0
 11 20  1  6  0  0  0
 21 10  1  0  0  0  0
 21 16  2  0  0  0  0
 22  6  2  0  0  0  0
 23  8  1  0  0  0  0
 24 12  2  0  0  0  0
 25 18  2  0  0  0  0
 26 18  1  0  0  0  0
 27 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28  7  1  0  0  0  0
 28 17  1  0  0  0  0
 11 29  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015224

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CSC1=C(N)C(=O)C=C2OC3=C(C=C(C=O)C=C3)N=C12)(N=C(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H15N3O6S/c1-8(23)20-11(18(25)26)7-28-17-15(19)12(24)5-14-16(17)21-10-4-9(6-22)2-3-13(10)27-14/h2-6,11H,7,19H2,1H3,(H,20,23)(H,25,26)/t11-/m0/s1

> <INCHI_KEY>
CBXHEDPBKOZZSI-NSHDSACASA-N

> <FORMULA>
C18H15N3O6S

> <MOLECULAR_WEIGHT>
401.39

> <EXACT_MASS>
401.068156389

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
39.05404743904024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-3-[(2-amino-8-formyl-3-oxo-3H-phenoxazin-1-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
0.8316721136666665

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.4119456456247175

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.157035575085397

> <JCHEM_PKA_STRONGEST_BASIC>
0.3980560107522132

> <JCHEM_POLAR_SURFACE_AREA>
151.64

> <JCHEM_REFRACTIVITY>
106.84639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-[(2-amino-8-formyl-3-oxophenoxazin-1-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   0.770   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  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334  10.010   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -2.667   7.700   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       4.001   5.390   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334  10.010   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0       1.334   6.930   0.000  0.00  0.00           S+0
HETATM   29  H   UNK     0      -0.000   6.160   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    3    9                                                       
CONECT    3    2   13                                                       
CONECT    4    9   10                                                       
CONECT    5   12   14                                                       
CONECT    6    9   22                                                       
CONECT    7   11   28                                                       
CONECT    8    1   20   23                                                  
CONECT    9    2    4    6                                                  
CONECT   10    4   13   21                                                  
CONECT   11    7   18   20   29                                             
CONECT   12    5   15   24                                                  
CONECT   13    3   10   27                                                  
CONECT   14    5   16   27                                                  
CONECT   15   12   17   19                                                  
CONECT   16   14   17   21                                                  
CONECT   17   15   16   28                                                  
CONECT   18   11   25   26                                                  
CONECT   19   15                                                            
CONECT   20    8   11                                                       
CONECT   21   10   16                                                       
CONECT   22    6                                                            
CONECT   23    8                                                            
CONECT   24   12                                                            
CONECT   25   18                                                            
CONECT   26   18                                                            
CONECT   27   13   14                                                       
CONECT   28    7   17                                                       
CONECT   29   11                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

Synonyms

Value	Source
1-((2-(Acetylamino)-2-carboxyethyl)thio)-2-amino-3-oxo-8-formyl-3H-phenoxiazine	MeSH

Molecular Formula

C₁₈H₁₅N₃O₆S

Average Mass

401.39

Monoisotopic Mass

401.068156389

IUPAC Name

(2R)-3-[(2-amino-8-formyl-3-oxo-3H-phenoxazin-1-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid

Traditional Name

(2R)-3-[(2-amino-8-formyl-3-oxophenoxazin-1-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CSC1=C(N)C(=O)C=C2OC3=C(C=C(C=O)C=C3)N=C12)(N=C(C)O)C(O)=O

InChI Identifier

InChI=1S/C18H15N3O6S/c1-8(23)20-11(18(25)26)7-28-17-15(19)12(24)5-14-16(17)21-10-4-9(6-22)2-3-13(10)27-14/h2-6,11H,7,19H2,1H3,(H,20,23)(H,25,26)/t11-/m0/s1

InChI Key

CBXHEDPBKOZZSI-NSHDSACASA-N

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
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Cysteine or derivatives
Alpha-amino acid or derivatives
Aryl thioether
Thiophenol ether
Aryl-aldehyde
Alkylarylthioether
Vinylogous thioester
Benzenoid
Acetamide
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Cyclic ketone
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Thioether
Sulfenyl compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organic nitrogen compound
Aldehyde
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Primary amine
Carbonyl group
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

L-cysteine derivative (CHEBI:73546 )
phenoxazine (CHEBI:73546 )
N-acetyl-amino acid (CHEBI:73546 )
arenecarbaldehyde (CHEBI:73546 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.01	ALOGPS
logP	0.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	0.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	151.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.85 m³·mol⁻¹	ChemAxon
Polarizability	39.05 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28639359

KEGG Compound ID

Not Available

BioCyc ID

CPD-14874

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464599

PDB ID

Not Available

ChEBI ID

73546

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Grixazone A (MMDBc0015224)

MOL for #<Metabolite:0x00007fecea579db8>

3D MOL for #<Metabolite:0x00007fecea579db8>

3D SDF for #<Metabolite:0x00007fecea579db8>

3D-SDF for #<Metabolite:0x00007fecea579db8>

PDB for #<Metabolite:0x00007fecea579db8>

3D PDB for #<Metabolite:0x00007fecea579db8>

SMILES for #<Metabolite:0x00007fecea579db8>

INCHI for #<Metabolite:0x00007fecea579db8>

Structure for #<Metabolite:0x00007fecea579db8>

3D Structure for #<Metabolite:0x00007fecea579db8>