P. aeruginosa Metabolome Database: 7-Aminomethyl-7-carbaguanine (PAMDB001851)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001851

Identification

Name:

7-Aminomethyl-7-carbaguanine

Description:

7-Aminomethyl-7-carbaguanine is one of the precursors of nucleoside Q (queuosine) biosynthesis. It is a substrate for preQ1 synthase (EC 1.7.1.13) which catalyzes the NADPH-dependent reduction of 7-cyano-7-carbaguanine (preQ0) to 7-aminomethyl-7-carbaguanine (preQ1). More specifically, this enzyme catalyzes the chemical reaction

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

7-Aminomethyl-7-carbaguanine
7-Aminomethyl-7-deazaguanine
PreQ1

Chemical Formula:

C₇H₉N₅O

Average Molecular Weight:

179.1793

Monoisotopic Molecular Weight:

179.080709935

InChI Key:

MEYMBLGOKYDGLZ-UHFFFAOYSA-N

InChI:

InChI=1S/C7H9N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,1,8H2,(H4,9,10,11,12,13)

CAS number:

Not Available

IUPAC Name:

2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one

Traditional IUPAC Name:

7-aminomethyl-7-deazaguanine

SMILES:

NCC1=CNC2=C1C(=O)NC(N)=N2

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrimidines

Sub Class

Not Available

Direct Parent

Pyrrolopyrimidines

Alternative Parents

Substituents

Pyrrolopyrimidine
Aralkylamine
Pyrimidone
Substituted pyrrole
Pyrimidine
Primary aromatic amine
Heteroaromatic compound
Vinylogous amide
Pyrrole
Lactam
Azacycle
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrrolopyrimidine (CHEBI:45126 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.93 mg/mL	ALOGPS
logP	-1.4	ALOGPS
logP	-1.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.04	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	109.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.67 m³·mol^-1	ChemAxon
Polarizability	17.44 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:

7-Aminomethyl-7-carbaguanine + 2 NADP > 7-Cyano-7-carbaguanine +2 NADPH
Guanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + Guanine
Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine
7-Aminomethyl-7-carbaguanine + NADP <> 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguanine
7-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + Guanine

Pathways:

Folate biosynthesis pae00790
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0900000000-186cf56f77e8ac46162e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-e42a8c4daace1afde7ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-1900000000-d9d17cbc8d643eb3bb92	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-7c00db685d48eeeaa166	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-2900000000-8a8ba88dc9cf497add5e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-8d2f3dc2af852732e95b	View in MoNA

References

References:

Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	45126
HMDB ID	HMDB11690
Pubchem Compound ID	171
Kegg ID	C16675
ChemSpider ID	166
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	PRF

7-Aminomethyl-7-carbaguanine (PAMDB001851)

Structure for 7-Aminomethyl-7-carbaguanine (PAMDB001851)