(2S,3S,4S,5R,6S)-6-{[2-amino-6-imino-4-(piperidin-1-yl)-1,6-dihydropyrimidin-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174642
• Molecular Formular: C15H23N5O7
• Molecular Mass: 385.37242
• Monoisotopic Mass: 385.1597481
• SMILES: C1CCN(CC1)c1cc(=N)n(c(n1)N)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](On2c(N)nc(cc2=N)N2CCCCC2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H23N5O7/c16-7-6-8(19-4-2-1-3-5-19)18-15(17)20(7)27-14-11(23)9(21)10(22)12(26-14)13(24)25/h6,9-12,14,16,21-23H,1-5H2,(H2,17,18)(H,24,25)/t9-,10-,11+,12-,14-/m0/s1
• InChIKey: WLRKVVVPBPEJRI-HNRZYHPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-amino-6-imino-4-(piperidin-1-yl)-1,6-dihydropyrimidin-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-amino-6-imino-4-(piperidin-1-yl)pyrimidin-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6-(1-Piperidinyl)-2,4-pyrimidinediamine-3-oxide Glucuronide; 1-[[4-Amino-2-imino-6-(1-piperidinyl)-1(2H)-pyrimidinyl]oxy]-1-deoxy-β-D-glucopyranuronic Acid; Minoxidil β-D-Glucuronide

Database IDs

• CAS Number: 56828-40-1
• PubChem SID: 164230552
• PubChem CID: 71750747

CALCULATED PROPERTIES

• Acid pKa: 3.1992364
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -2.9740386
• LogD (pH = 7.4): -2.9934747
• Log P: -2.9733052
• Molar Refractivity: 109.5442 cm^3
• Polarizability: 34.88865 Å^3
• Polar Surface Area: 185.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Methanol; Water
• Apperance: Off-White to Yellow Solid
• Melting Point: 132-133°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M345050

Minoxidil β-D-Glucuronide is a metabolite of Minoxidil (M345000), an antihypertensive and antialopecia agent. Minoxidil activates ATP-activated K+ channels.

REFERENCES

• Thomas, R.C., et al.: J. Pharmaceut. Sci., 64, 1366 (1975)