NP-MRD: Showing NP-Card for 7-Aminomethyl-7-carbaguanine (NP0091561)

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Record Information

Version

2.0

Created at

2022-05-11 18:41:21 UTC

Updated at

2022-05-11 18:41:21 UTC

NP-MRD ID

NP0091561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Aminomethyl-7-carbaguanine

Description

7-Aminomethyl-7-carbaguanine, also known as 7-deaza-7-aminomethyl-guanine or PREQ1, 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. A pyrrolopyrimidine that is 7-deazaguanine bearing an aminomethyl substituent at the 7 position. 7-Aminomethyl-7-carbaguanine is a very strong basic compound (based on its pKa). 7-Aminomethyl-7-carbaguanine exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201502D          

 13 14  0  0  0  0            999 V2000
   10.8729   -9.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8729   -8.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584   -9.9795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584   -8.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4440   -9.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4440   -8.7420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6575   -9.8218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1423   -9.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6574   -8.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584   -7.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7295   -9.9795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9122   -7.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7191   -7.5308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  2  1  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
  9  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091561

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCC1=CNC2=C1C(=O)NC(N)=N2

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
MEYMBLGOKYDGLZ-UHFFFAOYSA-N

> <FORMULA>
C7H9N5O

> <MOLECULAR_WEIGHT>
179.1793

> <EXACT_MASS>
179.080709935

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.440777443981148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.43

> <JCHEM_LOGP>
-1.207994808333333

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.120217269603746

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.037900308457573

> <JCHEM_PKA_STRONGEST_BASIC>
8.601212537607308

> <JCHEM_POLAR_SURFACE_AREA>
109.28999999999999

> <JCHEM_REFRACTIVITY>
48.6742

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-aminomethyl-7-deazaguanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      20.296 -17.858   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.296 -16.318   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      18.962 -18.628   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      18.962 -15.548   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.629 -17.858   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      17.629 -16.318   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      21.761 -18.334   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      22.666 -17.088   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.760 -15.842   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.962 -14.008   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      16.295 -18.628   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      22.236 -14.378   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      23.742 -14.057   0.000  0.00  0.00           N+0
CONECT    1    3    7    2                                                  
CONECT    2    4    1    9                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6   10                                                  
CONECT    5    3    6   11                                                  
CONECT    6    4    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   12                                                  
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    9   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
7-DEAZA-7-aminomethyl-guanine	ChEBI
7-Aminomethyl-7-deazaguanine	Kegg
PreQ1	HMDB

Chemical Formula

C₇H₉N₅O

Average Mass

179.1793 Da

Monoisotopic Mass

179.08071 Da

IUPAC Name

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

Traditional Name

7-aminomethyl-7-deazaguanine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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)

InChI Key

MEYMBLGOKYDGLZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Aralkylamine
Hydroxypyrimidine
Substituted pyrrole
Pyrimidine
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrrolopyrimidine (CHEBI:45126 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon