Record Information
Version1.0
Creation date2011-09-21 00:10:04 UTC
Update date2015-07-21 06:57:03 UTC
Primary IDFDB022205
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Threoneopterin
DescriptionNeopterin is a catabolic product of GTP. It is synthesised by macrophages upon stimulation with interferon-gamma. It is used as a marker of HIV infection. It belongs to the chemical group known as pterins.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. [HMDB]
CAS Number2277-42-1
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.2 g/LALOGPS
logP-1.9ALOGPS
logP-3.2ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)8.18ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area152.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.35 m³·mol⁻¹ChemAxon
Polarizability23.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H11N5O4
IUPAC name2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one
InChI IdentifierInChI=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
Isomeric SMILESNC1=NC(=O)C2=C(N1)N=CC(=N2)[C@H](O)[C@@H](O)CO
Average Molecular Weight253.2147
Monoisotopic Molecular Weight253.081103865
Classification
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
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Threoneopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9720000000-dbaea74f5b1bab982cccSpectrum
Predicted GC-MSL-Threoneopterin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-023c-7224900000-d9995da3f870ce197e4eSpectrum
Predicted GC-MSL-Threoneopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Threoneopterin, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-36bea1b2a272e033358b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1190000000-2bd951c4e15d2dcd56402017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-9610000000-b9aa11f2bcd3fa5ffed72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-0390000000-ec5b9be8d84139270a9b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4950000000-b7d29b7f135e6846ba242017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-b1bd3092dbe5138a59152017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-65261128bc6509430eff2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-11or-0290000000-f3cc40a6df216d1989c92021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0910000000-65afaceb562a208674c52021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-d96c57d3adb198d365112021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0900000000-8381e93b0c0976ae85a32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-8900000000-cd88a729ae84c9be60122021-09-25View Spectrum
NMRNot Available
ChemSpider ID389684
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID440842
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00727
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDMPU
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
AnatidaeExpected but not quantifiedNot AvailableHMDB
BeefaloExpected but not quantifiedNot AvailableHMDB
BisonExpected but not quantifiedNot AvailableHMDB
BuffaloExpected but not quantifiedNot AvailableHMDB
Cattle (Beef, Veal)Expected but not quantifiedNot AvailableHMDB
ChickenExpected but not quantifiedNot AvailableHMDB
Columbidae (Dove, Pigeon)Expected but not quantifiedNot AvailableHMDB
DeerExpected but not quantifiedNot AvailableHMDB
Domestic goatExpected but not quantifiedNot AvailableHMDB
Domestic pigExpected but not quantifiedNot AvailableHMDB
Showing 1 to 10 of 29 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference