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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:15 UTC
HMDB IDHMDB0000845
Secondary Accession Numbers
  • HMDB0000838
  • HMDB00838
  • HMDB00845
Metabolite Identification
Common NameNeopterin
DescriptionNeopterin, also known as monapterin, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative and are mainly synthesized in several parts of the body, including the pineal gland. Neopterin is a solid that is soluble in water. Neopterin is a catabolic product of guanosine triphosphate (GTP). In humans, it is involved in pterine biosynthesis and it also serves as a precursor in the biosynthesis of biopterin, which is an essential cofactor in neurotransmitter synthesis. Neopterin has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. Uremic toxins can cause kidney, liver and heart damage. They can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Uremic toxins such as neopterin are actively transported into the kidneys via organic ion transporters (especially OAT3). Elevated levels of neopterin result from immune system activation, including from malignant cancer, allograft rejection, viral infection, and autoimmune disorders (PMID: 19500901 ). Measurement of neopterin concentration allows estimation of the extent of oxidative stress elicited by the immune system. Neopterin concentrations usually correlate with the extent and activity of a given disease, and are also used to monitor the course of the disease. Elevated neopterin concentrations are among the best predictors of adverse outcome in patients with HIV infection, in cardiovascular disease, and in various types of cancer.
Structure
Thumb
Synonyms
ValueSource
6-(D-erythro-1,2,3-Trihydroxypropyl)pterinHMDB
6-D-erythro-NeopterinHMDB
D-erythro-NeopterinHMDB
D-NeopterinHMDB
NeopterineHMDB
[S-(R*,s*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-ONHMDB
[S-(R*,s*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-oneHMDB
[S-(R*,s*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridine-4-oneHMDB
MonapterinMeSH, HMDB
Neopterin, (r*, r*)-isomerMeSH, HMDB
UmanopterinMeSH, HMDB
Neopterin, (erythro-D)-isomerMeSH, HMDB
2-amino-6-(1,2,3-Trihydroxypropyl)-4(3H)-pteridinoneMeSH, HMDB
Neopterin, (erythro-L)-isomerMeSH, HMDB
Neopterin, (threo-D)-isomerMeSH, HMDB
Neopterin, (threo-L)-isomerMeSH, HMDB
Chemical FormulaC9H11N5O4
Average Molecular Weight253.2147
Monoisotopic Molecular Weight253.081103865
IUPAC Name2-amino-6-(1,2,3-trihydroxypropyl)-3,4-dihydropteridin-4-one
Traditional Name2-amino-6-(1,2,3-trihydroxypropyl)-3H-pteridin-4-one
CAS Registry Number2009-64-5
SMILES
NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1
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)
InChI KeyBMQYVXCPAOLZOK-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available150.307http://allccs.zhulab.cn/database/detail?ID=AllCCS00000332
[M+H]+Not Available157.304http://allccs.zhulab.cn/database/detail?ID=AllCCS00000332
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Bone Marrow
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Leukocyte
  • Liver
  • Pancreas
  • Spleen
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
AIDS
  1. Ellaurie M, Calvelli T, Rubinstein A: Neopterin concentrations in pediatric human immunodeficiency virus infection as predictor of disease activity. Pediatr Infect Dis J. 1992 Apr;11(4):286-9. [PubMed:1565552 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Multiple sclerosis
  1. Shaw CE, Dunbar PR, Macaulay HA, Neale TJ: Measurement of immune markers in the serum and cerebrospinal fluid of multiple sclerosis patients during clinical remission. J Neurol. 1995 Jan;242(2):53-8. [PubMed:7707089 ]
Hydrocephalus
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
CNS tumors
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
CNS infections
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Parkinson's disease
  1. Furukawa Y, Nishi K, Mizuno Y, Narabayashi H: [Significance of CSF biopterin and neopterin in hereditary progressive dystonia with marked diurnal fluctuation (HPD)--a clue to pathogenesis]. No To Shinkei. 1995 Mar;47(3):261-8. [PubMed:7669428 ]
Urocanase deficiency
  1. Espinos C, Pineda M, Martinez-Rubio D, Lupo V, Ormazabal A, Vilaseca MA, Spaapen LJ, Palau F, Artuch R: Mutations in the urocanase gene UROC1 are associated with urocanic aciduria. J Med Genet. 2009 Jun;46(6):407-11. doi: 10.1136/jmg.2008.060632. Epub 2009 Mar 19. [PubMed:19304569 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Pterin-4a carbinolamine dehydratase deficiency
  1. Blaskovics M, Giudici TA: A new variant of biopterin deficiency. N Engl J Med. 1988 Dec 15;319(24):1611-2. doi: 10.1056/NEJM198812153192420. [PubMed:3200274 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112166
KNApSAcK IDC00007312
Chemspider ID4300
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeopterin
METLIN IDNot Available
PubChem Compound135408877
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000264
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References