Showing metabocard for 7,8-Dihydroneopterin (BMDB0002275)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:53:28 UTC
Update Date2020-05-21 16:29:04 UTC
BMDB IDBMDB0002275
Secondary Accession Numbers
  • BMDB02275
Metabolite Identification
Common Name7,8-Dihydroneopterin
Description2-Amino-6-[(1R,2S)-1,2,3-trihydroxypropyl]-7,8-dihydro-3H-pteridin-4-one, also known as 2-amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridine or 7,8-dihydro-D-neopterin, 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. 2-Amino-6-[(1R,2S)-1,2,3-trihydroxypropyl]-7,8-dihydro-3H-pteridin-4-one exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on 2-Amino-6-[(1R,2S)-1,2,3-trihydroxypropyl]-7,8-dihydro-3H-pteridin-4-one.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridineHMDB
2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridineHMDB
2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(1H)-oneHMDB
2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(3H)-oneHMDB
2-Amino-7,8-dihydro-6-(1,2,3-trihydroxypropyl)-4(1H)-pteridinoneHMDB
7,8-Dihydro-D-erythro-neopterinHMDB
7,8-Dihydro-D-neopterinHMDB
D-Erythro-7,8-dihydroneopterinHMDB
DihydroneopterinHMDB
NPRHMDB
7,8-Dihydro-neopterinHMDB
Chemical FormulaC9H13N5O4
Average Molecular Weight255.2306
Monoisotopic Molecular Weight255.096753929
IUPAC Name2-amino-6-(1,2,3-trihydroxypropyl)-1,4,7,8-tetrahydropteridin-4-one
Traditional Name2-amino-6-(1,2,3-trihydroxypropyl)-7,8-dihydro-1H-pteridin-4-one
CAS Registry Number1218-98-0
SMILES
NC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)CO)N1
InChI Identifier
InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)
InChI KeyYQIFAMYNGGOTFB-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
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Ketimine
  • Secondary alcohol
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Polyol
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-3.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.37ChemAxon
pKa (Strongest Basic)0.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area152.56 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity69.66 m³·mol⁻¹ChemAxon
Polarizability23.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9220000000-602126fb02cae16969f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0aw9-3292200000-e6b52358cd355e939ab0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_31) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_34) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a4i-0090000000-c40ef232ef8c10af6b4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0090000000-40779978322477cf298aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-0090000000-e49838b4e8d652d72bdfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0a4r-0390000000-b43231e2e78443a996d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-014i-0920000000-5f6d06fef1bff433cb74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-014i-0900000000-1f59c6362ecd3bf94b79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-014i-0900000000-5299b47c47609ee94a30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-014i-1900000000-f31d91ebf5d2ad43354cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-01ba-3900000000-4d3e2458159bb9f65ce6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-00xs-6900000000-86a6eac4069432a18ae5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-00r7-9600000000-971378f9c783f6d800ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-014l-9200000000-687b58605bb70fc727dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-014i-9000000000-b01418dfcc77acb66b6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-014i-0900000000-5da76eb2e54c7dcf9422View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-014i-0900000000-df54ce2cbff970a469f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-004i-0900000000-d6756ef30d881fb25685View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-001l-0900000000-e8baecab87622e9340c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-0w29-0900000000-4952089b8c8b79285deaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-0ab9-0690000000-1f127d1244a709e9919fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-e5dad4abb411efa4feb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1790000000-449cabdd2508eefabcccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-3900000000-b2abed21008ce5fb01bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1390000000-1e1c831e7f68ac77caedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4950000000-948e3120b1a4f548982bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-581b6b2fd47ffbefaa0cView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0244465
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022940
KNApSAcK IDNot Available
Chemspider ID639
KEGG Compound IDC04874
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6588
PubChem Compound659
PDB IDNot Available
ChEBI ID17001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sepiapterin reductase
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
Q17QK8
Molecular weight:
28939.0
Reactions
Sepiapterin + NADPH → 7,8-Dihydroneopterin + NADPdetails
Enzyme Details
2. Carbonyl reductase [NADPH] 1
General function:
Lipid transport and metabolism
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione (By similarity).
Gene Name:
CBR1
Uniprot ID:
Q3SZD7
Molecular weight:
30533.0
Reactions
Sepiapterin + NADP → 7,8-Dihydroneopterin + NADPHdetails
Enzyme Details
3. Dihydrofolate reductase
General function:
Coenzyme transport and metabolism
Specific function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFR2 (By similarity).
Gene Name:
DHFR
Uniprot ID:
P00376
Molecular weight:
21604.0
Reactions
7,8-Dihydroneopterin + NADPH → NADP + Tetrahydrobiopterin + Waterdetails