(Z)-N,N'-dicyclohexylmorpholine-4-carboximidamide; {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(morpholin-4-yl)phosphinic acid

• ChemBase ID: 134072
• Molecular Formular: C31H52N9O9P
• Molecular Mass: 725.773241
• Monoisotopic Mass: 725.36256092
• SMILES: c1nc2c(n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(N1CCOCC1)O)O)O)[nH]c(nc2=O)N.C1CCC(CC1)N/C(=N/C1CCCCC1)/N1CCOCC1
• Canonical SMILES: C1CCC(CC1)N/C(=N/C1CCCCC1)/N1CCOCC1.Nc1nc(=O)c2c([nH]1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(N1CCOCC1)O
• InChI: InChI=1S/C17H31N3O.C14H21N6O8P/c1-3-7-15(8-4-1)18-17(20-11-13-21-14-12-20)19-16-9-5-2-6-10-16;15-14-17-11-8(12(23)18-14)16-6-20(11)13-10(22)9(21)7(28-13)5-27-29(24,25)19-1-3-26-4-2-19/h15-16H,1-14H2,(H,18,19);6-7,9-10,13,21-22H,1-5H2,(H,24,25)(H3,15,17,18,23)/t;7-,9-,10-,13-/m.1/s1
• InChIKey: CFNWUGDJWKRMBL-VAMAKUSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (Z)-N,N'-dicyclohexylmorpholine-4-carboximidamide; {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(morpholin-4-yl)phosphinic acid
• IUPAC Traditional name: (Z)-N,N'-dicyclohexylmorpholine-4-carboximidamide; [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(morpholin-4-yl)phosphinic acid
• Synonyms: MDCC; Guanosine 5′-monophosphomorpholidate 4-morpholine-N,N′-dicyclohexylcarboxamidine salt

Database IDs

• CAS Number: 7361-07-1
• MDL Number: MFCD00079328
• PubChem SID: 162228349
• PubChem CID: 10974612

CALCULATED PROPERTIES

• Acid pKa: 2.1302304
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -4.9730783
• LogD (pH = 7.4): -5.1292815
• Log P: -3.3830032
• Molar Refractivity: 95.4639 cm^3
• Polarizability: 36.996597 Å^3
• Polar Surface Area: 193.99 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ~95%

DETAILS

Sigma Aldrich - G7627

Application
Guanosine 5′-monophosphomorpholidate may be used to synthesize guanosine diphosphate sugars such as GDP-fucose, GDP-mannose, UDP-galactose, and other more complex sugars nucleotides.