(1S,2R)-1-(2-amino-4-hydroxypteridin-6-yl)propane-1,2,3-triol

• ChemBase ID: 139020
• Molecular Formular: C9H11N5O4
• Molecular Mass: 253.21474
• Monoisotopic Mass: 253.08110386
• SMILES: c1c(nc2c(n1)nc(nc2O)N)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H](c1cnc2c(n1)c(O)nc(n2)N)O)O
• InChI: 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
• InChIKey: BMQYVXCPAOLZOK-XINAWCOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-1-(2-amino-4-hydroxypteridin-6-yl)propane-1,2,3-triol
• IUPAC Traditional name: (1S,2R)-1-(2-amino-4-hydroxypteridin-6-yl)propane-1,2,3-triol
• Synonyms: D-erythro-Neopterin; D-(+)-Neopterin; D-赤型新蝶呤; D-(+)-新蝶呤

Database IDs

• CAS Number: 2009-64-5
• EC Number: 217-924-7
• MDL Number: MFCD00042801
• Beilstein Number: 89070
• PubChem SID: 162233271; 24897641
• PubChem CID: 448839

CALCULATED PROPERTIES

• Acid pKa: 10.362922
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.9563227
• LogD (pH = 7.4): -1.953541
• Log P: -1.9530337
• Molar Refractivity: 60.9221 cm^3
• Polarizability: 22.918821 Å^3
• Polar Surface Area: 158.5 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +52±2°, c = 0.3% in 0.1 M HCl

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.5% (sum of enantiomers, HPLC); 99%
• Empirical Formula (Hill Notation): C9H11N5O4

DETAILS

Sigma Aldrich - N3386

Biochem/physiol Actions
Pterin cofactor; precursor of BH4 (tetrahydrobiopterin).
Packaging
10, 25, 100 mg in poly bottle

Sigma Aldrich - 72147

Other Notes
Biochemistry and clinical use as a marker for cellular immune reactions, review1