(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

• ChemBase ID: 129790
• Molecular Formular: C9H15N5O3
• Molecular Mass: 241.2471
• Monoisotopic Mass: 241.11748937
• SMILES: O=c1nc([nH]c2NC[C@@H](Nc12)[C@@H](O)[C@@H](O)C)N
• Canonical SMILES: C[C@@H]([C@@H]([C@H]1CNc2c(N1)c(=O)nc([nH]2)N)O)O
• InChI: InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
• InChIKey: FNKQXYHWGSIFBK-RPDRRWSUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one
• IUPAC Traditional name: tetrahydrobiopterin
• Synonyms: Tetrahydrobiopterin

Database IDs

• CAS Number: 17528-72-2
• PubChem SID: 162224078
• PubChem CID: 44257
• CHEBI ID: 59560
• ATC CODE: A16AX07
• CHEMBL: 1201774
• Chemspider ID: 40270
• DrugBank ID: DB00360
• Wikipedia Title: Tetrahydrobiopterin

CALCULATED PROPERTIES

• Acid pKa: 10.009284
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.6650207
• LogD (pH = 7.4): -2.6631784
• Log P: -2.6621299
• Molar Refractivity: 68.4334 cm^3
• Polarizability: 22.361328 Å^3
• Polar Surface Area: 132.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 4 hours (healthy adults); 6–7 hours (PKU patients)
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)
• US Licence: Kuvan