MiMeDB: Showing metabocard for (1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid (MMDBc0032889)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:30 UTC

Update Date

2022-08-31 21:45:12 UTC

Metabolite ID

MMDBc0032889

Metabolite Identification

Common Name

(1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid

Description

A member of the class of phenazines that is 1,4,10,10a-tetrahydrophenazine substituted at positions 1 and 6 by carboxy groups (the 1R,10aS-diastereomer).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307102019332D          

 21 23  0  0  1  0            999 V2000
   -2.1453    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013    0.4124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1453   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1453    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439    0.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4439   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453   -2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426   -2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1453    2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426    2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 14 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  9 21  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032889

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12NC3=C(N=C1CC=C[C@H]2C(O)=O)C(=CC=C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12N2O4/c17-13(18)7-3-1-5-9-11(7)16-10-6-2-4-8(14(19)20)12(10)15-9/h1-5,8,12,15H,6H2,(H,17,18)(H,19,20)/t8-,12+/m1/s1

> <INCHI_KEY>
CUYPWOPOBAHCCE-PELKAZGASA-N

> <FORMULA>
C14H12N2O4

> <MOLECULAR_WEIGHT>
272.26

> <EXACT_MASS>
272.079706874

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.70537810868951

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
0.5567975213178517

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9387269372046263

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0806007998659277

> <JCHEM_PKA_STRONGEST_BASIC>
5.378173449807117

> <JCHEM_POLAR_SURFACE_AREA>
98.99000000000001

> <JCHEM_REFRACTIVITY>
74.8764

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-20         0                                  
HETATM    1  C   UNK     0      -4.004   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.004  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.695  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.309  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.309   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.695   1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.309  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.309   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.695  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.004  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.004   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.695   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.695  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.004  -3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.386  -3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.695   3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.004   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.386   3.850   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       2.695   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14   21                                             
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   18                                                  
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

Synonyms

Value	Source
(1R,10AS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylate	Generator

Molecular Formula

C₁₄H₁₂N₂O₄

Average Mass

272.26

Monoisotopic Mass

272.079706874

IUPAC Name

(1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid

Traditional Name

(1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12NC3=C(N=C1CC=C[C@H]2C(O)=O)C(=CC=C3)C(O)=O

InChI Identifier

InChI=1S/C14H12N2O4/c17-13(18)7-3-1-5-9-11(7)16-10-6-2-4-8(14(19)20)12(10)15-9/h1-5,8,12,15H,6H2,(H,17,18)(H,19,20)/t8-,12+/m1/s1

InChI Key

CUYPWOPOBAHCCE-PELKAZGASA-N

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
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Amino acid
Ketimine
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Secondary amine
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Imine
Amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.6	ALOGPS
logP	0.56	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	5.38	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.88 m³·mol⁻¹	ChemAxon
Polarizability	26.71 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Proteobacteria	4	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

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

58163531

KEGG Compound ID

Not Available

BioCyc ID

CPD-19103

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119058149

PDB ID

Not Available

ChEBI ID

132262

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (1R,10aS)-1,4,10,10a-tetrahydrophenazine-1,6-dicarboxylic acid (MMDBc0032889)

MOL for #<Metabolite:0x00007fed080c99a8>

3D MOL for #<Metabolite:0x00007fed080c99a8>

3D SDF for #<Metabolite:0x00007fed080c99a8>

3D-SDF for #<Metabolite:0x00007fed080c99a8>

PDB for #<Metabolite:0x00007fed080c99a8>

3D PDB for #<Metabolite:0x00007fed080c99a8>

SMILES for #<Metabolite:0x00007fed080c99a8>

INCHI for #<Metabolite:0x00007fed080c99a8>

Structure for #<Metabolite:0x00007fed080c99a8>

3D Structure for #<Metabolite:0x00007fed080c99a8>