Hmdb loader
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:58:50 UTC
HMDB IDHMDB0000727
Secondary Accession Numbers
  • HMDB00727
Metabolite Identification
Common NameL-Threoneopterin
DescriptionL-Threoneopterin is a catabolic product of GTP. It is synthesized by macrophages upon stimulation by interferon-gamma. It is used as a marker of HIV infection. It belongs to the chemical group known as pterins. Neopterin is a pteridine derivative present in body fluids; elevated levels result from immune system activation, malignant disease, allograft rejection, and viral infections (From Stedman, 26th ed). Neopterin also serves as a precursor in the biosynthesis of biopterin.
Structure
Thumb
Synonyms
ValueSource
2-Amino-6-(L-threo-trihydroxypropyl)-4(3H)-pteridinoneHMDB
L-(+)-MonapterinHMDB
L-6-(Threo-1',2',3'-trihydroxypropyl)pterinHMDB
L-MonapterinHMDB
L-Threo-monapterinHMDB
L-Threo-neopterinHMDB
2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinoneHMDB
Neopterin, (erythro-L)-isomerHMDB
MonapterinHMDB
NeopterinHMDB
Neopterin, (threo-L)-isomerHMDB
2-Amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-4(3H)-pteridinoneHMDB
L-6-(Threo-1’,2’,3’-trihydroxypropyl)pterinHMDB
Chemical FormulaC9H11N5O4
Average Molecular Weight253.2147
Monoisotopic Molecular Weight253.081103865
IUPAC Name2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one
Traditional Name2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-8H-pteridin-4-one
CAS Registry Number2277-42-1
SMILES
NC1=NC(=O)C2=NC(=CNC2=N1)[C@H](O)[C@@H](O)CO
InChI Identifier
InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m0/s1
InChI KeyBMQYVXCPAOLZOK-NJGYIYPDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Pyrazine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Polyol
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022205
KNApSAcK IDNot Available
Chemspider ID389684
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5695
PubChem Compound440842
PDB IDNot Available
ChEBI ID49751
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceViscontini, Max; Provenzale, R.; Ohlgart, S.; Mallevialle, J. Pterin chemistry. XXXII. Synthesis of natural D-neopterin and L-monapterin. Helvetica Chimica Acta (1970), 53(5), 1202-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available