MiMeDB: Showing metabocard for (1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylic acid (MMDBc0032888)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:28 UTC

Update Date

2022-08-31 21:45:11 UTC

Metabolite ID

MMDBc0032888

Metabolite Identification

Common Name

(1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylic acid

Description

A member of the class of phenazines that is 1,4,5,5a,6,9-hexahydrophenazine substituted at positions 1 and 6 by carboxy groups (the 1R,5aS,6R-diastereomer).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307102019272D          

 21 23  0  0  1  0            999 V2000
    2.1450   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7012    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7012   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1450    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1450   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4437    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1450   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  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  6  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
  4 21  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032888

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12NC3=C(N=C1CC=C[C@H]2C(O)=O)[C@@H](C=CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2O4/c17-13(18)7-3-1-5-9-11(7)16-10-6-2-4-8(14(19)20)12(10)15-9/h1-4,7-8,11,16H,5-6H2,(H,17,18)(H,19,20)/t7-,8-,11+/m1/s1

> <INCHI_KEY>
MUDZFKKAMBPIJZ-XLDPMVHQSA-N

> <FORMULA>
C14H14N2O4

> <MOLECULAR_WEIGHT>
274.276

> <EXACT_MASS>
274.095356939

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.167150174856715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylic acid

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
-1.9270295928606291

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.197813532742921

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4717545837474937

> <JCHEM_PKA_STRONGEST_BASIC>
5.489389380596236

> <JCHEM_POLAR_SURFACE_AREA>
98.99000000000001

> <JCHEM_REFRACTIVITY>
73.8231

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-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       2.618   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   21                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
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    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

Synonyms

Value	Source
(1R,5AS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylate	Generator

Molecular Formula

C₁₄H₁₄N₂O₄

Average Mass

274.276

Monoisotopic Mass

274.095356939

IUPAC Name

(1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylic acid

Traditional Name

(1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12NC3=C(N=C1CC=C[C@H]2C(O)=O)[C@@H](C=CC3)C(O)=O

InChI Identifier

InChI=1S/C14H14N2O4/c17-13(18)7-3-1-5-9-11(7)16-10-6-2-4-8(14(19)20)12(10)15-9/h1-4,7-8,11,16H,5-6H2,(H,17,18)(H,19,20)/t7-,8-,11+/m1/s1

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	0.77	ALOGPS
logP	-1.9	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	5.49	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	73.82 m³·mol⁻¹	ChemAxon
Polarizability	27.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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_2_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	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

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	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

Exposure Sources

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

58163530

KEGG Compound ID

Not Available

BioCyc ID

CPD-12990

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119058147

PDB ID

Not Available

ChEBI ID

132261

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Huang W, Brewer LK, Jones JW, Nguyen AT, Marcu A, Wishart DS, Oglesby-Sherrouse AG, Kane MA, Wilks A: PAMDB: a comprehensive Pseudomonas aeruginosa metabolome database. Nucleic Acids Res. 2018 Jan 4;46(D1):D575-D580. doi: 10.1093/nar/gkx1061. [PubMed:29106626 ]

Showing metabocard for (1R,5aS,6R)-1,4,5,5a,6,9-hexahydrophenazine-1,6-dicarboxylic acid (MMDBc0032888)

MOL for #<Metabolite:0x00007fdb718c7ce8>

3D MOL for #<Metabolite:0x00007fdb718c7ce8>

3D SDF for #<Metabolite:0x00007fdb718c7ce8>

3D-SDF for #<Metabolite:0x00007fdb718c7ce8>

PDB for #<Metabolite:0x00007fdb718c7ce8>

3D PDB for #<Metabolite:0x00007fdb718c7ce8>

SMILES for #<Metabolite:0x00007fdb718c7ce8>

INCHI for #<Metabolite:0x00007fdb718c7ce8>

Structure for #<Metabolite:0x00007fdb718c7ce8>

3D Structure for #<Metabolite:0x00007fdb718c7ce8>