D-Neopterin - ≥98%(HPLC), sum of enantiomers , CAS No.2009-64-5

CAS: 2009-64-5 Cat. No.: D137509 Molecular Weight: 253.21 Beilstein Registry Number: 89070 EC Number: 217-924-7

GRADE & PURITY ≥98%(HPLC), sum of enantiomers

Synonyms

4(8H)-pteridinone, 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]- | [S-(R*,S*)]-2-Amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-on | 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-1H-pteridin-4-one | BMQYVXCPAOLZOK-XINAWCOVSA-N | AS-56644 | 6-(D-erythro-1,2,3-T

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

D-Neopterin is a precursor of tetrahydrobiopterin and can be used as a biochemical marker indicative of cell proliferation. Elevated levels of D-Neopterin are correlated to immune system activation, malignant disease, allograft rejection, and viral infections. Additionally, D-Neopterin serves as a cofactor for pterin in biological systems.

Specifications

Synonyms

4(8H)-pteridinone, 2-amino-6-[(1S, 2R)-1, 2, 3-trihydroxypropyl]- | [S-(R*, S*)]-2-Amino-6-(1, 2, 3-trihydroxypropyl)-1H-pteridin-4-on | 2-amino-6-[(1S, 2R)-1, 2, 3-trihydroxypropyl]-1H-pteridin-4-one | BMQYVXCPAOLZOK-XINAWCOVSA-N | AS-56644 | 6-(D-erythro-1, 2, 3-T

Specifications & Purity

≥98%(HPLC), sum of enantiomers

Biochemical and Physiological Mechanisms

Pterin cofactor; precursor of BH4 (tetrahydrobiopterin).Prognostic marker of immunodeficiency. Precursor of biopterin . Synthesized in response to interferon-γ stimulation. Indicates level of activation of T helper cell 1 derived cellular immune activatio

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504773243
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773243
• Canonical Smiles: C1=C(N=C2C(=O)NC(=NC2=N1)N)C(C(CO)O)O
• IUPAC Name: 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-3H-pteridin-4-one
• InChIKey: BMQYVXCPAOLZOK-XINAWCOVSA-N
• 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)/t4-,6+/m1/s1
• Isomeric SMILES: C1=C(N=C2C(=O)NC(=NC2=N1)N)[C@@H]([C@@H](CO)O)O
• WGK Germany: 3
• Molecular Weight: 253.21
• Beilstein: 89070
• Reaxy-Rn: 258082
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=258082&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pteridines and derivatives
      • Subclass Pterins and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pteridines and derivatives
• Subclass: Pterins and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Biopterins and derivatives
• Alternative Parents: Pyrimidones Aminopyrimidines and derivatives Pyrazines Vinylogous amides Heteroaromatic compounds Secondary alcohols Polyols Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This 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.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO (20 mM, with gentle warming), 0.05M NaOH, 1M HCl, aqueous acid, and water (very slightly). Ultrasonication may improve the dissolution.
• Molecular Weight: 253.220 g/mol
• XLogP3: -3.500
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 253.081 Da
• Monoisotopic Mass: 253.081 Da
• Topological Polar Surface Area: 154.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 363.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xueyan Gou, Fenglin Ran, Jinru Yang, Yanrong Ma, Xin’an Wu.  (2022)  Construction and Evaluation of a Novel Organic Anion Transporter 1/3 CRISPR/Cas9 Double-Knockout Rat Model.  Pharmaceutics,  14  (11): (2307).  [PMID:36365126] [10.3390/pharmaceutics14112307]