MiMeDB: Showing metabocard for 7-Cyano-7-carbaguanine (MMDBc0030136)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:55:17 UTC

Update Date

2022-08-31 17:40:00 UTC

Metabolite ID

MMDBc0030136

Metabolite Identification

Common Name

7-Cyano-7-carbaguanine

Description

7-cyano-7-carbaguanine is a member of the chemical class known as Pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. This compound is involved in queuosine biosynthesis.

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241207102D          

 13 14  0  0  0  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -2.9346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  8  3  0  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  6 13  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030136

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=NC(=N)NC2=C1C(=CN2)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C7H5N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,(H4,9,10,11,12,13)

> <INCHI_KEY>
FMKSMYDYKXQYRV-UHFFFAOYSA-N

> <FORMULA>
C7H5N5O

> <MOLECULAR_WEIGHT>
175.1475

> <EXACT_MASS>
175.049409807

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
15.88423832972297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
0.10701953308602707

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.938289776709645

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.9086137716244798

> <JCHEM_PKA_STRONGEST_BASIC>
18.63976133203084

> <JCHEM_POLAR_SURFACE_AREA>
108.05

> <JCHEM_REFRACTIVITY>
56.5035

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-cyano-7-deazaguanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.220  -5.478   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       5.198   0.237   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    3   10                                                       
CONECT    3    1    2    4                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   10   11                                                  
CONECT    6    4   12   13                                                  
CONECT    7    9   11   12                                                  
CONECT    8    1                                                            
CONECT    9    7                                                            
CONECT   10    2    5                                                       
CONECT   11    5    7                                                       
CONECT   12    6    7                                                       
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
2-AMINO-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carbonitrile	ChEBI
7-CN-7-DeazaG	ChEBI
PreQ(0)	ChEBI
7-Cyano-7-deazaguanine	Kegg
PreQ(0) compound	MeSH

Molecular Formula

C₇H₅N₅O

Average Mass

175.1475

Monoisotopic Mass

175.049409807

IUPAC Name

4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Traditional Name

7-cyano-7-deazaguanine

CAS Registry Number

Not Available

SMILES

OC1=NC(=N)NC2=C1C(=CN2)C#N

InChI Identifier

InChI=1S/C7H5N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,(H4,9,10,11,12,13)

InChI Key

FMKSMYDYKXQYRV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrimidines

Sub Class

Pyrrolo[2,3-d]pyrimidines

Direct Parent

Pyrrolo[2,3-d]pyrimidines

Alternative Parents

Substituents

Pyrrolo[2,3-d]pyrimidine
Aminopyrimidine
Pyrimidone
Pyrimidine
Substituted pyrrole
Heteroaromatic compound
Vinylogous amide
Pyrrole
Carbonitrile
Nitrile
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nitrile (CHEBI:45075 )
pyrrolopyrimidine (CHEBI:45075 )
a small molecule (7-CYANO-7-DEAZAGUANINE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.21 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	0.11	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	18.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.05 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.5 m³·mol⁻¹	ChemAxon
Polarizability	15.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	366	Human ; Human feces; Human feces; pleural fluid plaque; bal; Pig ; Cattle ; River trout ; Turkey ; Sheep ; Lion ; Chicken ; American dog tick	Unknown
Bacteria	Cyanobacteria	29	Human
Bacteria	Firmicutes	80	Human feces; Human ; Cattle
Bacteria	Aquificae	3
Bacteria	Bacteroidetes	7	Human ; Human feces
Bacteria	Chlorobi	11
Bacteria	Elusimicrobia	1
Bacteria	Actinobacteria	2
Bacteria	Spirochaetes	6	Human
Bacteria	Planctomycetes	1
Bacteria	nah	1
Bacteria	Thermotogae	3
Bacteria	Chloroflexi	1
Bacteria/NULL	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Pig ; Cattle ; River trout ; Turkey ; Sheep ; Lion ; Chicken ; American dog tick	Unknown
Bacteria	Acidobacteria	2
Archaea/Archaea	Crenarchaeota	4	Human feces
Archaea/Archaea	Euryarchaeota	30	Human feces; Human
Archaea	Euryarchaeota	2	Human feces; Human
Archaea	Crenarchaeota	1	Human feces

Exposure Sources

Other Exposures

Source Type	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

DB03074

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15996

BioCyc ID

7-CYANO-7-DEAZAGUANINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

446357

PDB ID

Not Available

ChEBI ID

45075

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 7-Cyano-7-carbaguanine (MMDBc0030136)

MOL for #<Metabolite:0x0000560bdf348028>

3D MOL for #<Metabolite:0x0000560bdf348028>

3D SDF for #<Metabolite:0x0000560bdf348028>

3D-SDF for #<Metabolite:0x0000560bdf348028>

PDB for #<Metabolite:0x0000560bdf348028>

3D PDB for #<Metabolite:0x0000560bdf348028>

SMILES for #<Metabolite:0x0000560bdf348028>

INCHI for #<Metabolite:0x0000560bdf348028>

Structure for #<Metabolite:0x0000560bdf348028>

3D Structure for #<Metabolite:0x0000560bdf348028>