7,8-dihydroneopterin 3'-phosphate (YMDB00668)

Identification

YMDB ID

YMDB00668

Name

7,8-dihydroneopterin 3'-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Dihydroneopterin phosphate 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. Dihydroneopterin phosphate exists in all living species, ranging from bacteria to plants to humans. In yeast, dihydroneopterin phosphate is involved in the metabolic pathway called the tetrahydrofolate biosynthesis pathway. Based on a literature review a significant number of articles have been published on Dihydroneopterin phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate
Dihydroneopterin phosphate
7,8-Dihydroneopterin 3'-phosphate
2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphoric acid
7,8-Dihydroneopterin 3'-phosphoric acid
Dihydroneopterin phosphoric acid
2-Amino-6-[(1S,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-7,8-dihydro-4(3H)-pteridinone
7,8-Dihydroneopterin 3’-phosphate

CAS number

Not Available

Weight

Average: 335.2105
Monoisotopic: 335.063084339

InChI Key

PLSQMGZYOGSOCE-XINAWCOVSA-N

InChI

InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1

IUPAC Name

[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy]phosphonic acid

Traditional IUPAC Name

(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxyphosphonic acid

Chemical Formula

C₉H₁₄N₅O₇P

SMILES

NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(O)=O)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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
1,2-diol
Ketimine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Imine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterin phosphate (CHEBI:48954 )
dihydropterin (CHEBI:48954 )
neopterins (CHEBI:48954 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	5.26 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	0.18	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.53 m³·mol⁻¹	ChemAxon
Polarizability	28.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

tetrahydrofolate biosynthesis

PW002417

KEGG Pathways

Folate biosynthesis

ec00790

SMPDB Reactions

Not Available

KEGG Reactions

water + 7,8-dihydroneopterin 3'-phosphate → phosphate + 7,8-Dihydroneopterin

7,8-dihydroneopterin 3'-triphosphate + water → Pyrophosphate + 7,8-dihydroneopterin 3'-phosphate + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-8911000000-53dc19c24dbe99c4297c	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03dj-9412400000-711e5bff9c050e651d6f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1149000000-5fbd207fae24db394e97	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-3984000000-b1316677bed07bd7f55d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ka-1910000000-4900a3a0b1a8c45967d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003u-6519000000-d97b00fd24549be11a57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-17032e05ed4e9517e10d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-767fc48b2593a3849c9a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0049000000-34ddec995961538a2b69	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0093000000-9db5d730be4336945735	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1910000000-fbf02f9608828a708ae3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-9008000000-046b0ad106139a51dfcc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a3ddbffe59a79724cf9e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-3e79dacf1a5decbc02d9	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

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:

Resource	Link
CHEBI ID	48954
HMDB ID	HMDB0006824
Pubchem Compound ID	25245170
Kegg ID	C05925
ChemSpider ID	21865614
FOODB ID	FDB024104
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. ATPase GET3

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

7,8-dihydroneopterin 3'-phosphate (YMDB00668)

Structure for #<Compound:0xaa196c20>

Enzymes

Reactions