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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:25 UTC
HMDB IDHMDB00845
Secondary Accession Numbers
  • HMDB00838
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
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
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 KeyInChIKey=BMQYVXCPAOLZOK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Pyrimidone
  • Pyrimidine
  • Pyrazine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.11 m3·mol-1ChemAxon
Polarizability23.34 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-3a09212908092a492f4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-054y-0920000000-6241d1b694e32019a927View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mp-4900000000-877883fea7e0d415c840View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-bd6cd1a1bfbd14b712cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1190000000-2cfad581ae89edd75d7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-9610000000-935c14541b2551e1a2aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1490000000-873c74c47753e32ed9f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-4950000000-0c17274f2f41e583bbd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-8ae2879ae5357154c5d1View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Activated T-Lymphocytes
  • Bone Marrow
  • Brain
  • Central Nervous System
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Liver
  • Lymphocyte
  • Pancreas
  • Skin
  • Spleen
  • T-Lymphocyte
Pathways
NameSMPDB LinkKEGG Link
Dopa-responsive dystoniaSMP00486Not Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiencySMP00487Not Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)SMP00488Not Available
Hyperphenylalaninemia due to dhpr-deficiencySMP00489Not Available
Pterine BiosynthesisSMP00005map00790
Segawa syndromeSMP00490Not Available
Sepiapterin reductase deficiencySMP00491Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 Quantified0.002-0.014 uMChildren (1-13 years old)MaleNormal 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
BiofluidStatusValueAgeSexConditionReferenceDetails
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 Quantified0.0226 +/- 0.001 uMNot SpecifiedNot Specifiedidiopathic parkinsonisam details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0252 +/- 0.0022 uMNot SpecifiedNot Specifieddopa-nonresponsive dystonia 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. [1565552 ]
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. [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. [8583213 ]
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. [8583213 ]
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. [7707089 ]
Associated OMIM IDs
DrugBank IDDB02385
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005562
KNApSAcK IDNot Available
Chemspider ID4300
KEGG Compound IDC05926
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeopterin
NuGOwiki LinkHMDB00845
Metagene LinkHMDB00845
METLIN ID248
PubChem Compound4455
PDB ID1BR5
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. [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. [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. [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. [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. [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. [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. [12409735 ]
  8. Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [14531816 ]