(2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^{2,6}]dodeca-8,11-dien-10-one

• ChemBase ID: 4188
• Molecular Formular: C9H10N2O5
• Molecular Mass: 226.1861
• Monoisotopic Mass: 226.05897143
• SMILES: OC[C@H]1O[C@@H]2[C@@H](Oc3nc(=O)ccn23)[C@@H]1O
• Canonical SMILES: OC[C@H]1O[C@@H]2[C@H]([C@@H]1O)Oc1n2ccc(=O)n1
• InChI: InChI=1S/C9H10N2O5/c12-3-4-6(14)7-8(15-4)11-2-1-5(13)10-9(11)16-7/h1-2,4,6-8,12,14H,3H2/t4-,6-,7+,8-/m1/s1
• InChIKey: UUGITDASWNOAGG-CCXZUQQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^{2,6}]dodeca-8,11-dien-10-one; (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^2,^6]dodeca-8,11-dien-10-one
• IUPAC Traditional name: cyclouridine
• Synonyms: 2,2'-Anhydro-1(B-D-arabinofuranosyl)uracil; 2,2'-O-Cyclouridine; ANU; 2,2'-Anhydrouridine; O2,2'-Cyclouridine; Cyclouridine; O2,2′-Cyclouridine; O2,2′-环尿苷

Database IDs

• CAS Number: 3736-77-4
• EC Number: 223-107-6
• MDL Number: MFCD00004945
• PubChem SID: 160967620; 46505052; 24859440
• PubChem CID: 806138

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.978741
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.2669369
• LogD (pH = 7.4): -1.266938
• Log P: -1.2669369
• Molar Refractivity: 49.7752 cm^3
• Polarizability: 19.688475 Å^3
• Polar Surface Area: 91.59 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.64
• LOG S: -0.6
• Solubility (Water): 5.62e+01 g/l

PROPERTIES

Physical Property

• Melting Point: 248-251 °C(lit.)
• Optical Rotation: [α]19/D -21°, c = 4 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 98%; 99%
• Empirical Formula (Hill Notation): C9H10N2O5

DETAILS

DrugBank - DB04627

Drug information: experimental

Sigma Aldrich - 324442

Packaging
1, 5 g in glass bottle
Application
Research tool for antiviral and anticancer studies.1