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Record Information

Version

2.0

Creation Date

2012-07-30 14:54:47 -0600

Update Date

2015-06-03 17:20:49 -0600

Secondary Accession Numbers

ECMDB21183

Identification

Name:

7-Deaza-7-carboxyguanine

Description

7-deaza-7-carboxyguanine 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carboxylate
2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carboxylic acid
7-Deaza-7-carboxyguanine

Chemical Formula:

C₇H₆N₄O₃

Weight:

Average: 194.1475
Monoisotopic: 194.043990078

InChI Key:

XIUIRSLBMMTDSK-UHFFFAOYSA-N

InChI:

InChI=1S/C7H6N4O3/c8-7-10-4-3(5(12)11-7)2(1-9-4)6(13)14/h1H,(H,13,14)(H4,8,9,10,11,12)

CAS number:

Not Available

IUPAC Name:

2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

Traditional IUPAC Name:

2-amino-4-oxo-1H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

SMILES:

[H]OC(=O)C1=C([H])N([H])C2=C1C(=O)N=C(N([H])[H])N2[H]

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
Pyrrole-3-carboxylic acid
Pyrrole-3-carboxylic acid or derivatives
Aminopyrimidine
Pyrimidone
Pyrimidine
Substituted pyrrole
Heteroaromatic compound
Vinylogous amide
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:61125 )
pyrrolopyrimidine (CHEBI:61125 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.96 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.16	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.21	ChemAxon
pKa (Strongest Basic)	0.05	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + 7-Deaza-7-carboxyguanine + Ammonium > ADP + Hydrogen ion + Water + Phosphate + 7-Cyano-7-carbaguanine
6-Carboxy-5,6,7,8-tetrahydropterin <> 7-Carboxy-7-carbaguanine + Ammonia + 7-Deaza-7-carboxyguanine
7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate > 7-Cyano-7-carbaguanine + ADP + Inorganic phosphate + Water
6-Carboxy-5,6,7,8-tetrahydropterin > 7-Deaza-7-carboxyguanine + Ammonia
7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate <> 7-Cyano-7-carbaguanine + ADP + Phosphate + Water
7-Deaza-7-carboxyguanine + Adenosine triphosphate + Ammonium > Water + Phosphate + Adenosine diphosphate + Hydrogen ion + 7-Cyano-7-carbaguanine + ADP

SMPDB Pathways:

Folate biosynthesis	PW000908
preQ0 metabolism	PW001893

KEGG Pathways:

Folate biosynthesis ec00790
Metabolic pathways eco01100

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-bf9e486de51c440522d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0900000000-58f4e55d1aebe6f5cceb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7s-1900000000-46af04c26b8110735f23	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0005-0900000000-765de4deda0d7402eb4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-3900000000-a3e8ab6eeb37a9fb7c5f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3900000000-86c7751b7a5c749304c4	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	61125
HMDB ID	Not Available
Pubchem Compound ID	13344694
Kegg ID	C20248
ChemSpider ID	26332127
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 7-cyano-7-deazaguanine synthase

General function:: Involved in argininosuccinate synthase activity
Specific function:: Catalyzes the ATP-dependent conversion of 7-carboxy-7- deazaguanine (CDG) to 7-cyano-7-deazaguanine (preQ(0))
Gene Name:: queC
Uniprot ID:: P77756
Molecular weight:: 25514

Reactions

7-carboxy-7-carbaguanine + NH(3) + ATP = 7-cyano-7-carbaguanine + ADP + phosphate + H(2)O.

Protein Details

2. 7-carboxy-7-deazaguanine synthase; queosine biosynthesis

General function:: Not Available
Specific function:: Not Available
Gene Name:: queE
Uniprot ID:: P64554
Molecular weight:: Not Available

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7-Deaza-7-carboxyguanine (M2MDB001592)

Structure for #<Compound:0xa78983b4>

Enzymes

Reactions