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Identification
YMDB IDYMDB00579
Name7,8-Dihydroneopterin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description7,8-Dihydroneopterin 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. 7,8-Dihydroneopterin is a strong basic compound (based on its pKa). 7,8-Dihydroneopterin exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine
  • 2-Amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridine
  • 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(1H)-one
  • 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(3H)-one
  • 2-Amino-7,8-dihydro-6-(1,2,3-trihydroxypropyl)-4(1H)-pteridinone
  • 7,8-Dihydro-D-erythro-neopterin
  • 7,8-Dihydro-D-neopterin
  • 7,8-Dihydroneopterin
  • D-erythro-7,8-Dihydroneopterin
  • Dihydroneopterin
  • NPR
  • 7,8-Dihydro-neopterin
  • 2-Amino-4-hydroxy-6-(D-erythro-1’,2’,3’-trihydroxypropyl)-7,8-dihydropteridine
  • 2-Amino-7,8-dihydro-6-[(1S,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone
CAS number1218-98-0
WeightAverage: 255.2306
Monoisotopic: 255.096753929
InChI KeyYQIFAMYNGGOTFB-XINAWCOVSA-N
InChIInChI=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)/t4-,6+/m1/s1
IUPAC Name2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one
Traditional IUPAC Name2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydro-1H-pteridin-4-one
Chemical FormulaC9H13N5O4
SMILESNC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)CO)C(=O)N1
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.86 g/LALOGPS
logP-2.1ALOGPS
logP-3.3ChemAxon
logS-2.1ALOGPS
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
Polarizability24 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
SMPDB Reactions
7,8-DihydroneopterinGlycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
KEGG Reactions
7,8-dihydroneopterin 3'-triphosphate + waterphosphate + 7,8-Dihydroneopterin + hydron
7,8-DihydroneopterinGlycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
water + 7,8-dihydroneopterin 3'-phosphatephosphate + 7,8-Dihydroneopterin
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-00l5-1910400000-bd112529d925635514cdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00di-2932500000-19e8700372faabe73f7aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9640000000-11b256f7a4e39d238a0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1390000000-7a17dedde70317d006b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-3950000000-1106781b3c6d170aa292JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-0904e10b066f91e855dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0090000000-f50197d1f13af4158233JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1790000000-ad8f0148941de4b772efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-4900000000-9c19a9151f80a11b997bJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17001
HMDB IDHMDB02275
Pubchem Compound ID659
Kegg IDC04874
ChemSpider ID24816137
FOODB IDFDB030616
Wikipedia IDNot Available
BioCyc IDDIHYDRONEOPTERIN-P3

Enzymes

General function:
Involved in catalytic activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO8
Uniprot ID:
P11491
Molecular weight:
63003.60156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
(2E,6E)-farnesyl diphosphate + H(2)O → (2E,6E)-farnesol + diphosphate.
beta-D-fructose 2,6-bisphosphate + H2O → beta-D-fructofuranose 2-phosphate + phosphate
General function:
Inorganic ion transport and metabolism
Specific function:
ATPase required for the post-translational delivery of tail-anchored (TA) proteins to the endoplasmic reticulum. Recognizes and selectively binds the transmembrane domain of TA proteins in the cytosol. This complex then targets to the endoplasmic reticulum by membrane-bound receptors GET1 and GET2, where the tail-anchored protein is released for insertion. This process is regulated by ATP binding and hydrolysis. ATP binding drives the homodimer towards the closed dimer state, facilitating recognition of newly synthesized TA membrane proteins. ATP hydolysis is required for insertion. Subsequently, the homodimer reverts towards the open dimer state, lowering its affinity for the GET1-GET2 receptor, and returning it to the cytosol to initiate a new round of targeting. Cooperates with the HDEL receptor ERD2 to mediate the ATP-dependent retrieval of resident ER proteins that contain a C-terminal H-D-E-L retention signal from the Golgi to the ER. Involved in low-level resistance to the oxyanions arsenite and arsenate, and in heat tolerance
Gene Name:
GET3
Uniprot ID:
Q12154
Molecular weight:
39353.39844
Reactions
General function:
Involved in dihydropteroate synthase activity
Specific function:
Catalyzes three sequential steps of tetrahydrofolate biosynthesis
Gene Name:
FOL1
Uniprot ID:
P53848
Molecular weight:
93119.10156
Reactions
2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine → 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine → AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate → diphosphate + dihydropteroate.