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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:11 UTC
HMDB IDHMDB0000845
Secondary Accession Numbers
  • HMDB0000838
  • HMDB00838
  • HMDB00845
Metabolite Identification
Common NameNeopterin
DescriptionNeopterin 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
Data?1547234111
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
MonapterinHMDB
Neopterin, (r*, r*)-isomerHMDB
UmanopterinHMDB
Neopterin, (erythro-D)-isomerHMDB
2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinoneHMDB
Neopterin, (erythro-L)-isomerHMDB
Neopterin, (threo-D)-isomerHMDB
Neopterin, (threo-L)-isomerHMDB
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 effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.26 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.99ChemAxon
pKa (Strongest Basic)0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.95 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.11 m³·mol⁻¹ChemAxon
Polarizability23.34 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-9720000000-287de905bc263a1d3fefJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0pb9-3393300000-91821528c6f566d17174JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-3a09212908092a492f4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-054y-0920000000-6241d1b694e32019a927JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mp-4900000000-877883fea7e0d415c840JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-bd6cd1a1bfbd14b712cfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1190000000-2cfad581ae89edd75d7aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-9610000000-935c14541b2551e1a2aeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1490000000-873c74c47753e32ed9f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-4950000000-0c17274f2f41e583bbd6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-8ae2879ae5357154c5d1JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Activated T-Lymphocytes
  • Bone Marrow
  • Brain
  • Central Nervous System
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Liver
  • Lymphocyte
  • Pancreas
  • Skin
  • Spleen
  • T-Lymphocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0060 +/- 0.0016 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0150 +/- 0.0041 uMAdult (>18 years old)Not SpecifiedNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.005 +/- 0.002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0038 +/- 0.0022 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.018 +/- 0.002 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0252 +/- 0.002 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0110-0.0240 uMAdolescent (13-18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002-0.014 uMChildren (1-13 years old)MaleNormal details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.0+/-0.8 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.21 +/- 0.08 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.23 +/- 0.08 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.36 +/- 0.07 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.4 +/- 0.71 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0347 +/- 0.0250 uMChildren (1-13 years old)BothAIDS details
BloodDetected and Quantified0.33 +/- 0.04 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified0.0050 +/- 0.0028 uMAdult (>18 years old)BothMultiple sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01175 (0.008-0.0155) uMChildren (1-13 years old)Malesepiapterin reductase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0091 +/- 0.0074 uMAdult (>18 years old)Not SpecifiedMultiple Sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.001 uMAdult (>18 years old)Not SpecifiedHydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.023 +/- 0.01 uMAdult (>18 years old)Not SpecifiedCNS Tumors details
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 +/- 0.083 uMAdult (>18 years old)Not SpecifiedCNS Infections details
Cerebrospinal Fluid (CSF)Detected and Quantified0.009 uMAdolescent (13-18 years old)Not AvailableUrocanase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0226 +/- 0.001 uMNot SpecifiedNot Specifiedidiopathic parkinsonisam details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0252 +/- 0.0022 uMNot SpecifiedNot Specifieddopa-nonresponsive dystonia details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
UrineDetected and Quantified22.6 umol/mmol creatinineNewborn (0-30 days old)FemaleHyperphenylalaninemia due to pterin-4a-carbinolamine dehydratase details
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
FoodDB IDFDB005562
KNApSAcK IDNot Available
Chemspider ID4300
KEGG Compound IDC05926
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeopterin
METLIN ID248
PubChem Compound4455
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  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 ]
  2. 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:12689700 ]
  3. 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 ]
  4. 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:7855550 ]
  5. 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:3940654 ]
  6. 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:6602425 ]
  7. 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:12409735 ]
  8. Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. [PubMed:3326735 ]
  9. 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:12498998 ]
  10. 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:14621776 ]
  11. 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:2117813 ]
  12. 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:16099770 ]
  13. 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:1282321 ]
  14. 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:16012455 ]
  15. 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:9550574 ]
  16. 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:9163857 ]
  17. 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:1430106 ]
  18. 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:3698305 ]
  19. 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:8228365 ]
  20. 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:14531816 ]