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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

ECMDB21181

Identification

Name:

6-Hydroxymethyl dihydropterin

Description

6-hydroxymethyl dihydropterin is a member of the chemical class known as Pterins and Derivatives. These are polycyclic aromatic compounds containing a pterin moeity, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Amino-4-hydroxy-6-hydroxymethyl dihydropteridin
Dihydropterin-CH2OH

Chemical Formula:

C₇H₉N₅O₂

Weight:

Average: 195.1787
Monoisotopic: 195.075624557

InChI Key:

CQQNNQTXUGLUEV-UHFFFAOYSA-N

InChI:

InChI=1S/C7H9N5O2/c8-7-11-5-4(6(14)12-7)10-3(2-13)1-9-5/h13H,1-2H2,(H4,8,9,11,12,14)

CAS number:

Not Available

IUPAC Name:

2-amino-6-(hydroxymethyl)-3,4,7,8-tetrahydropteridin-4-one

Traditional IUPAC Name:

2-amino-6-(hydroxymethyl)-7,8-dihydro-3H-pteridin-4-one

SMILES:

NC1=NC2=C(N=C(CO)CN2)C(=O)N1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Secondary aliphatic/aromatic amine
Hydroxypyrimidine
Pyrimidine
Heteroaromatic compound
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Imine
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydropterin (CHEBI:17083 )
a small molecule (AMINO-OH-HYDROXYMETHYL-DIHYDROPTERIDINE )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.47 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.62	ChemAxon
pKa (Strongest Basic)	0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.86 m³·mol⁻¹	ChemAxon
Polarizability	18.4 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:

SMPDB Pathways:

Folate biosynthesis	PW000908
GTP degradation	PW001888

KEGG Pathways:

Folate biosynthesis ec00790
Metabolic pathways eco01100

EcoCyc Pathways:

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02t9-1900000000-5cfea5c037994f006216	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-9f8713d042cc448282c0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-443afedc044efb6836ef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-2900000000-143274abf0f8afadfb00	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-7d20bbe8055a463789f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01r6-1900000000-56b39cb20c728828c72a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-32e7a15f26d685ec66bc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-e6264bd1af5f7597a2c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-2046c8dbdea1405f54d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-4900000000-8df0786ac08c282820b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-d9a36ecaf7ce4795a113	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1900000000-695ce544726c989be876	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-441d6e22f231bf631645	View in MoNA
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:

Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17083
HMDB ID	HMDB0304227
Pubchem Compound ID	218
Kegg ID	C01300
ChemSpider ID	213
Wikipedia ID	Not Available
BioCyc ID	AMINO-OH-HYDROXYMETHYL-DIHYDROPTERIDINE
EcoCyc ID	AMINO-OH-HYDROXYMETHYL-DIHYDROPTERIDINE
Ligand Expo	PH2

Enzymes

Protein Details

1. Dihydropteroate synthase

General function:: Involved in dihydropteroate synthase activity
Specific function:: DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide
Gene Name:: folP
Uniprot ID:: P0AC13
Molecular weight:: 30615

Reactions

(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate = diphosphate + dihydropteroate.

Protein Details

2. Dihydroneopterin aldolase

General function:: Involved in dihydroneopterin aldolase activity
Specific function:: Catalyzes the conversion of 7,8-dihydroneopterin to 6- hydroxymethyl-7,8-dihydropterin. Can use L-threo-dihydroneopterin and D-erythro-dihydroneopterin as substrates for the formation of 6-hydroxymethyldihydropterin, but it can also catalyze the epimerization of carbon 2' of dihydroneopterin and dihydromonapterin at appreciable velocity
Gene Name:: folB
Uniprot ID:: P0AC16
Molecular weight:: 13619

Reactions

2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.

Protein Details

3. 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase

General function:: Involved in 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine diphosphokinase activity
Specific function:: ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8- dihydropteridine = AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6- yl)methyl diphosphate
Gene Name:: folK
Uniprot ID:: P26281
Molecular weight:: 18079

Reactions

ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine = AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.

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6-Hydroxymethyl dihydropterin (M2MDB001590)

Structure for #<Compound:0xad112d28>

Enzymes

Reactions

Reactions

Reactions