2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one

• ChemBase ID: 126161
• Molecular Formular: C9H11N5O3
• Molecular Mass: 237.21534
• Monoisotopic Mass: 237.08618924
• SMILES: O=c1nc([nH]c2ncc(nc12)[C@@H](O)[C@@H](O)C)N
• Canonical SMILES: C[C@@H]([C@@H](c1cnc2c(n1)c(=O)nc([nH]2)N)O)O
• InChI: InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1
• InChIKey: LHQIJBMDNUYRAM-DZSWIPIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one
• IUPAC Traditional name: 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
• Synonyms: (1’R,2’S)-Biopterin; 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine; L-erythro-6-(1,2-Dihydroxypropyl)pterin; 6-Biopterin; Biopterin

Database IDs

• CAS Number: 22150-76-1
• EC Number: 244-807-8
• MDL Number: MFCD00036787
• Beilstein Number: 87860
• PubChem SID: 162220502; 24891654
• PubChem CID: 445040
• Chemspider ID: 392795
• KEGG ID: C06313
• MeSH Name: Biopterin
• Wikipedia Title: Biopterin

CALCULATED PROPERTIES

• Acid pKa: 7.598084
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.1910951
• LogD (pH = 7.4): -1.3875011
• Log P: -1.1878132
• Molar Refractivity: 58.1331 cm^3
• Polarizability: 21.483948 Å^3
• Polar Surface Area: 133.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -65±8°, c = 0.2% in 0.1 M HCl

Safety Information

• RTECS: UO3506000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97%; ≥98.0% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C9H11N5O3

DETAILS

Sigma Aldrich - B2517

Application
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer.

Sigma Aldrich - 14390

Other Notes
Review: Chemical mechanisms in the action of pteridine coenzymes1