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

2024-10-13 14:41:57 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

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	splash10-004i-0900000000-af2ae62c4c215361eced	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0900000000-9e5f5f67428ff03e8e27	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1900000000-370668da5ccac92b10dc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-03d09ff2a0e7426078a9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-38453df754a7089d2db4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-2a2f03d4b6dc173ec6ad	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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	368	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; 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	Acidobacteria	2
Archaea/Archaea	Crenarchaeota	4
Archaea/Archaea	Euryarchaeota	30
Archaea	Euryarchaeota	2
Archaea	Crenarchaeota	1

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

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

References

Synthesis Reference

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:0x00007fdb3d93fba0>

3D MOL for #<Metabolite:0x00007fdb3d93fba0>

3D SDF for #<Metabolite:0x00007fdb3d93fba0>

3D-SDF for #<Metabolite:0x00007fdb3d93fba0>

PDB for #<Metabolite:0x00007fdb3d93fba0>

3D PDB for #<Metabolite:0x00007fdb3d93fba0>

SMILES for #<Metabolite:0x00007fdb3d93fba0>

INCHI for #<Metabolite:0x00007fdb3d93fba0>

Structure for #<Metabolite:0x00007fdb3d93fba0>

3D Structure for #<Metabolite:0x00007fdb3d93fba0>