4-amino-5-hydroxymethyl-2-methylpyrimidine (CHEBI:16892)

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CHEBI:16892 - 4-amino-5-hydroxymethyl-2-methylpyrimidine

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ChEBI Name	4-amino-5-hydroxymethyl-2-methylpyrimidine

ChEBI ID	CHEBI:16892

Definition	An aminopyrimidine that is pyrimidine in which the hydrogens at positions 2, 4, and 5 are replaced by methyl, amino, and hydroxymethyl substituents, respectively.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:1781, CHEBI:43206, CHEBI:11957, CHEBI:20312

Supplier Information	ChemicalBook:CB21075560, eMolecules:1976115, ZINC000000895559

Download	Molfile XML SDF

more structures >>

Molfile

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Mrv0541 08131413343D

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Mrv0541 08131413343D

19 19 0 0 0 0 999 V2000

0.4850 0.0000 3.3310 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3850 0.0000 1.0660 N 0 0 0 0 0 0 0 0 0 0 0 0

0.3140 0.0000 1.8330 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9020 -0.0040 1.3280 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.0910 0.0010 0.0120 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3720 0.0010 -0.5150 N 0 0 0 0 0 0 0 0 0 0 0 0

0.0220 0.0000 -0.8290 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2780 0.0000 -0.2550 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1410 0.0000 -2.3270 C 0 0 1 0 0 0 0 0 0 0 0 0

1.1460 0.0000 -2.9470 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9960 -0.0010 -3.9030 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6920 -0.8890 -2.6320 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6910 0.8900 -2.6330 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1630 0.0000 -0.8740 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1400 0.0010 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5000 0.0000 -1.4760 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5270 1.0280 3.6920 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3570 -0.5120 3.7930 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4110 -0.5130 3.5900 H 0 0 0 0 0 0 0 0 0 0 0 0

1 3 1 0 0 0 0

1 17 1 0 0 0 0

1 18 1 0 0 0 0

1 19 1 0 0 0 0

2 3 4 0 0 0 0

2 8 4 0 0 0 0

3 4 4 0 0 0 0

4 5 4 0 0 0 0

5 6 1 0 0 0 0

5 7 4 0 0 0 0

6 15 1 0 0 0 0

6 16 1 0 0 0 0

7 8 4 0 0 0 0

7 9 1 0 0 0 0

8 14 1 0 0 0 0

9 10 1 0 0 0 0

9 12 1 0 0 0 0

9 13 1 0 0 0 0

10 11 1 0 0 0 0

M END): 21 ms

reading 19 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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19 atoms created

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Formula

C6H9N3O

Net Charge

Average Mass

139.15520

Monoisotopic Mass

139.07456

InChI

InChI=1S/C6H9N3O/c1-4-8-2-5(3-10)6(7)9-4/h2,10H,3H2,1H3,(H2,7,8,9)

InChIKey

VUTBELPREDJDDH-UHFFFAOYSA-N

SMILES

Cc1ncc(CO)c(N)n1

Metabolite of Species	Details
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	4-amino-5-hydroxymethyl-2-methylpyrimidine (CHEBI:16892) has role Escherichia coli metabolite (CHEBI:76971) 4-amino-5-hydroxymethyl-2-methylpyrimidine (CHEBI:16892) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) 4-amino-5-hydroxymethyl-2-methylpyrimidine (CHEBI:16892) is a aminopyrimidine (CHEBI:38338) 4-amino-5-hydroxymethyl-2-methylpyrimidine (CHEBI:16892) is a aromatic primary alcohol (CHEBI:33857)

IUPAC Name

(4-amino-2-methylpyrimidin-5-yl)methanol

Synonyms	Sources
2-methyl-4-amino-5-hydroxymethylpyrimidine	ChemIDplus
4-amino-2-methyl-5-hydroxymethylpyrimidine	ChEBI
4-amino-2-methyl-5-pyrimidinemethanol	ChEBI
4-Amino-2-methyl-5-pyrimidinemethanol	KEGG COMPOUND
4-Amino-5-hydroxymethyl-2-methylpyrimidine	KEGG COMPOUND
4-amino-5-hydroxymethyl-2-methylpyrimidine	UniProt
Atoxopyrimidine	ChemIDplus
Pyramin	ChemIDplus
Pyramine	ChemIDplus
Toxopyrimidine	KEGG COMPOUND

Manual Xrefs	Databases
C00007494	KNApSAcK
C01279	KEGG COMPOUND
DB02022	DrugBank
HMH	PDBeChem
HMP	MetaCyc
View more database links

Registry Numbers	Types	Sources
126858	Reaxys Registry Number	Reaxys
73-67-6	CAS Registry Number	KEGG COMPOUND
73-67-6	CAS Registry Number	ChemIDplus

Citation

Wrenger C, Eschbach ML, Müller IB, Laun NP, Begley TP, Walter RD (2006)
Vitamin B1 de novo synthesis in the human malaria parasite Plasmodium falciparum depends on external provision of 4-amino-5-hydroxymethyl-2-methylpyrimidine.
Biological chemistry 387, 41-51 [PubMed:16497163]
[show Abstract]

Last Modified

25 January 2016

CHEBI:16892 - 4-amino-5-hydroxymethyl-2-methylpyrimidine

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