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Human Metabolome Database Version 2.5

 

Showing metabocard for Neopterin (HMDB00845)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2010-04-22 11:48:48
Accession Number HMDB00845
Secondary Accession Numbers HMDB00838
Common Name Neopterin
Description 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.
Synonyms
  1. 6-(D-erythro-1,2,3-Trihydroxypropyl)pterin
  2. 6-D-erythro-Neopterin
  3. D-Neopterin
  4. D-erythro-Neopterin
  5. [S-(R*,S*)]-2-Amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-on
  6. [S-(R*,S*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-one
  7. [S-(R*,S*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridine-4-one
  8. neopterin
  9. neopterine
Chemical IUPAC Name 1-(2-amino-4-hydroxy-pteridin-6-yl)propane-1,2,3-triol
Chemical Formula C9H11N5O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Pterins
Sub Class
  • Miscellaneous pterins
Family
  • Mammalian Metabolite
Species
  • primary alcohol
  • secondary alcohol
  • 1,2-diol
  • primary amine
  • primary aromatic amine
  • oxo(het)arene
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 253.215
Monoisotopic Molecular Weight 253.081100
Isomeric SMILES NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1
Canonical SMILES NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1
KEGG Compound ID C05926 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Neopterin Link Image
NuGOwiki Link HMDB00845 Link Image
Metagene Link HMDB00845 Link Image
METLIN ID 248 Link Image
PubChem Compound 440842 Link Image
PubChem Substance 8214 Link Image
ChEBI ID Not Available
CAS Registry Number 2009-64-5
InChI Identifier InChI=1/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)
Synthesis Reference Not Available
Melting Point (Experimental) N/A
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.26 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.75 [Predicted by ALOGPS]; -2.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1BR5 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
  • Urine
Tissue Location
Tissue References
Activated T-Lymphocytes —
Bone Marrow —
Brain —
Central Nervous System —
Erythrocyte —
Fibroblasts —
Kidney —
Liver —
Lymphocyte —
Pancreas —
Skin —
Spleen —
T-Lymphocyte —
Concentrations (Normal)
Biofluid Blood
Value 0.0150 +/- 0.0041 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 132. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Biofluid Blood
Value 0.0038 +/- 0.0022 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Blood
Value 0.0060 +/- 0.0016 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.018 +/- 0.002 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.01 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Gisslen M, Chiodi F, Fuchs D, Norkrans G, Svennerholm B, Wachter H, Hagberg L: Markers of immune stimulation in the cerebrospinal fluid during HIV infection: a longitudinal study. Scand J Infect Dis. 1994;26(5):523-33. [PubMed Link Image]
Biofluid CSF
Value 0.002-0.014 uM
Age Children:1-13 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • 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. Epub 2008 May 27. [PubMed Link Image]
Biofluid CSF
Value 0.0252 +/- 0.002 uM
Age N/A
Sex N/A
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.21 +/- 0.08 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Biofluid Urine
Value 0.23 +/- 0.08 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Biofluid Urine
Value 0.36 +/- 0.07 umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Biofluid Urine
Value 1.4 +/- 0.71 umol/mmol creatinine
Age Newborn:0-30 days old
Sex Both
Patient information Normal
Comments Not Available
References
  • Takahashi T, Kodama S, Nishio H, Takumi T, Matsuo T, Hase Y, Sawada Y: Transient hyperphenylalaninaemia with a high neopterin to biopterin ratio in urine. J Inherit Metab Dis. 1985;8(3):105-8. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.0050 +/- 0.0028 uM
Age Adult:>18 yrs old
Sex Both
Condition Multiple sclerosis
Comments Not Available
References
  • 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 Link Image]
Biofluid Blood
Value 0.0347 +/- 0.0250 uM
Age Children:1-13 yrs old
Sex Both
Condition AIDS
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.0091 +/- 0.0074 uM
Age Adult:>18 yrs old
Sex N/A
Condition Multiple sclerosis
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.01 +/- 0.001 uM
Age Adult:>18 yrs old
Sex N/A
Condition Hydrocephalus
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.023 +/- 0.01 uM
Age Adult:>18 yrs old
Sex N/A
Condition CNS tumors
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.12 +/- 0.083 uM
Age Adult:>18 yrs old
Sex N/A
Condition CNS infections
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.01175 (0.008-0.0155) uM
Age Children:1-13 yrs old
Sex Male
Comments Not Available
References
  • 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. Epub 2008 May 27. [PubMed Link Image]
Biofluid CSF
Value 0.0226 +/- 0.001 uM
Age N/A
Sex N/A
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.0252 +/- 0.0022 uM
Age N/A
Sex N/A
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition References
AIDS
  • 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 Link Image]
CNS infections
  • 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 Link Image]
CNS tumors
  • 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 Link Image]
Hydrocephalus
  • 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 Link Image]
Multiple sclerosis
  • 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 Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Pterine Biosynthesis SMP00005 Link Image map00790 Link Image
General References
  1. Azumagawa K, Suzuki S, Tanabe T, Wakamiya E, Kawamura N, Tamai H: Neopterin, biopterin, and nitric oxide concentrations in the cerebrospinal fluid of children with central nervous system infections. Brain Dev. 2003 Apr;25(3):200-2. [PubMed Link Image]
  2. 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 Link Image]
  3. Gisslen M, Chiodi F, Fuchs D, Norkrans G, Svennerholm B, Wachter H, Hagberg L: Markers of immune stimulation in the cerebrospinal fluid during HIV infection: a longitudinal study. Scand J Infect Dis. 1994;26(5):523-33. [PubMed Link Image]
  4. Reibnegger GJ, Bichler AH, Dapunt O, Fuchs DN, Fuith LC, Hausen A, Hetzel HM, Lutz H, Werner ER, Wachter H: Neopterin as a prognostic indicator in patients with carcinoma of the uterine cervix. Cancer Res. 1986 Feb;46(2):950-5. [PubMed Link Image]
  5. Niederwieser D, Huber C, Wachter H: [Neopterin, a new biochemical marker for the detection of activated T lymphocytes] Wien Klin Wochenschr. 1983 Mar 4;95(5):161-4. [PubMed Link Image]
  6. Abdulle S, Hagberg L, Svennerholm B, Fuchs D, Gisslen M: Continuing intrathecal immunoactivation despite two years of effective antiretroviral therapy against HIV-1 infection. AIDS. 2002 Nov 8;16(16):2145-9. [PubMed Link Image]
  7. Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. [PubMed Link Image]
  8. Kokcam I, Naziroglu M: Effects of vitamin E supplementation on blood antioxidants levels in patients with Behcet's disease. Clin Biochem. 2002 Nov;35(8):633-9. [PubMed Link Image]
  9. Margreiter R, Aichberger C, Konigsrainer A, Reibnegger G, Weiss G, Wachter H: Biliary neopterin for differentiation between liver allograft rejection and viral graft infection. Transpl Int. 1992;5 Suppl 1:S199-200. [PubMed Link Image]
  10. Steiner G, Zlabinger G, Karamehic J, Pohanka E, Kovarik J, Woloszczuk W: Interferon-gamma, neopterin, and interleukin-2 receptor levels in the serum of kidney transplant recipients. Transplant Proc. 1990 Aug;22(4):1857-8. [PubMed Link Image]
  11. Inci Fisenk B, Us D, Ozcebe OI, Hascelik G: The value of increased neopterin levels in reducing transfusion-transmitted virus infections: detection of a donation from a HBsAg positive chronic carrier by screening of neopterin in Turkish blood donors. Scand J Infect Dis. 2005;37(8):599-604. [PubMed Link Image]
  12. Antoniello S, Auletta M, Magri P, Russo N: Serum neopterin levels in patients with hepatocellular carcinoma. Biol Chem Hoppe Seyler. 1992 Nov;373(11):1165-8. [PubMed Link Image]
  13. Barani J, Nilsson JA, Mattiasson I, Lindblad B, Gottsater A: Inflammatory mediators are associated with 1-year mortality in critical limb ischemia. J Vasc Surg. 2005 Jul;42(1):75-80. [PubMed Link Image]
  14. Millner MM, Franthal W, Thalhammer GH, Berghold A, Aigner RM, Fuger GF, Reibnegger G: Neopterin concentrations in cerebrospinal fluid and serum as an aid in differentiating central nervous system and peripheral infections in children. Clin Chem. 1998 Jan;44(1):161-7. [PubMed Link Image]
  15. Muller TF, Trosch F, Ebel H, Grussner RW, Feiber H, Goke B, Greger B, Lange H: Pancreas-specific protein (PASP), serum amyloid A (SAA), and neopterin (NEOP) in the diagnosis of rejection after simultaneous pancreas and kidney transplantation. Transpl Int. 1997;10(3):185-91. [PubMed Link Image]
  16. Beckham JC, Caldwell DS, Peterson BL, Pippen AM, Currie MS, Keefe FJ, Weinberg JB: Disease severity in rheumatoid arthritis: relationships of plasma tumor necrosis factor-alpha, soluble interleukin 2-receptor, soluble CD4/CD8 ratio, neopterin, and fibrin D-dimer to traditional severity and functional measures. J Clin Immunol. 1992 Sep;12(5):353-61. [PubMed Link Image]
  17. Prior C, Bollbach R, Fuchs D, Hausen A, Judmaier G, Niederwieser D, Reibnegger G, Rotthauwe HW, Werner ER, Wachter H: Urinary neopterin, a marker of clinical activity in patients with Crohn's disease. Clin Chim Acta. 1986 Feb 28;155(1):11-21. [PubMed Link Image]
  18. Hagberg L, Dotevall L, Norkrans G, Larsson M, Wachter H, Fuchs D: Cerebrospinal fluid neopterin concentrations in central nervous system infection. J Infect Dis. 1993 Nov;168(5):1285-8. [PubMed Link Image]
  19. Toncheva D, Galabov AS, Laich A, Atanassova S, Kamarinchev B, Dimitrov T, Fuchs D: Urinary neopterin concentrations in patients with Balkan endemic nephropathy (BEN). Kidney Int. 2003 Nov;64(5):1817-21. [PubMed Link Image]
  20. 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 Link Image]
  21. Wikipedia Link Image