(6S)-2-amino-6-[(1R,2S)-1,2-dihydroxy(3,3,3-2H3)propyl]-3,4,5,6,7,8-hexahydropteridin-4-one

• ChemBase ID: 178288
• Molecular Formular: C9H15N5O3
• Molecular Mass: 241.2471
• Monoisotopic Mass: 241.11748937
• SMILES: [nH]1c(nc2c(c1=O)N[C@@H](CN2)[C@H]([C@@H](O)C)O)N
• Canonical SMILES: C[C@@H]([C@@H]([C@@H]1CNc2c(N1)c(=O)[nH]c(n2)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-FKZODXBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-2-amino-6-[(1R,2S)-1,2-dihydroxy(3,3,3-^2H₃)propyl]-3,4,5,6,7,8-hexahydropteridin-4-one
• IUPAC Traditional name: (6S)-2-amino-6-[(1R,2S)-1,2-dihydroxy(3,3,3-^2H₃)propyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one
• Synonyms: (6S)-2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone-d3 Disulfate; [6S-[6R*(1S*,2R*)]]-5,6,7,8-Tetrahydro-biopterin-d3 Disulfate; (6S)-Tetrahydro-L-biopterin-d3 Disulfate(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164234198
• PubChem CID: 71752418

CALCULATED PROPERTIES

• Acid pKa: 11.118297
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.373985
• LogD (pH = 7.4): -2.3219085
• Log P: -2.3211265
• Molar Refractivity: 68.6334 cm^3
• Polarizability: 22.361328 Å^3
• Polar Surface Area: 132.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T293182

The labelled S-enantiomer of Tetrahydro-L-biopterin. A natural cofactor for phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase, and nitric oxide synthase. An essential cofactor for the production of neurotransmitters such as catechola

REFERENCES

• Kwon, N.S., et al.: J. Biol. Chem., 264, 20498 (1989)
• Werner, E.R., et al.: Proc. Soc. Exp. Biol. Med., 203, 1 (1989)