MiMeDB: Showing metabocard for (1R,10aS)-1,4,10,10a-tetrahydrophenazine-1-carboxylic acid (MMDBc0032891)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:37 UTC

Update Date

2022-08-31 21:45:14 UTC

Metabolite ID

MMDBc0032891

Metabolite Identification

Common Name

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

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307102021242D          

 18 20  0  0  1  0            999 V2000
   -2.1449   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -0.2061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436    0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4436    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449    1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424    1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -0.6186    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
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  9 18  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032891

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-6,8,12,15H,7H2,(H,16,17)/t8-,12+/m1/s1

> <INCHI_KEY>
RMSOWPIMGWWPCR-PELKAZGASA-N

> <FORMULA>
C13H12N2O2

> <MOLECULAR_WEIGHT>
228.251

> <EXACT_MASS>
228.089877634

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.50254168384625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
0.7424359356104909

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.9491309435907

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0608675038484

> <JCHEM_PKA_STRONGEST_BASIC>
5.195128024191315

> <JCHEM_POLAR_SURFACE_AREA>
61.690000000000005

> <JCHEM_REFRACTIVITY>
67.62020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10aS)-1,4,10,10a-tetrahydrophenazine-1-carboxylic 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  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.004  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.695  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.309  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.309  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.695   0.385   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000  -2.695   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.309  -1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.309  -0.385   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.385   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.695  -2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.004  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.004  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.695   0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.695   1.925   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.004   2.695   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.386   2.695   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       2.695  -1.155   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   18                                             
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

Synonyms

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

Molecular Formula

C₁₃H₁₂N₂O₂

Average Mass

228.251

Monoisotopic Mass

228.089877634

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H12N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-6,8,12,15H,7H2,(H,16,17)/t8-,12+/m1/s1

InChI Key

RMSOWPIMGWWPCR-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
Benzenoid
Amino acid or derivatives
Ketimine
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Imine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
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	0.78 g/L	ALOGPS
logP	1.04	ALOGPS
logP	0.74	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.62 m³·mol⁻¹	ChemAxon
Polarizability	23.5 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_1_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)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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

58163532

KEGG Compound ID

Not Available

BioCyc ID

CPD-19105

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119058155

PDB ID

Not Available

ChEBI ID

132265

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-carboxylic acid (MMDBc0032891)

MOL for #<Metabolite:0x00007fed142ae730>

3D MOL for #<Metabolite:0x00007fed142ae730>

3D SDF for #<Metabolite:0x00007fed142ae730>

3D-SDF for #<Metabolite:0x00007fed142ae730>

PDB for #<Metabolite:0x00007fed142ae730>

3D PDB for #<Metabolite:0x00007fed142ae730>

SMILES for #<Metabolite:0x00007fed142ae730>

INCHI for #<Metabolite:0x00007fed142ae730>

Structure for #<Metabolite:0x00007fed142ae730>

3D Structure for #<Metabolite:0x00007fed142ae730>