[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid

• ChemBase ID: 133324
• Molecular Formular: C11H17N5O9P2
• Molecular Mass: 425.228302
• Monoisotopic Mass: 425.05015041
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(CP(=O)(O)O)O)O)O)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(CP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1
• InChIKey: OLCWZBFDIYXLAA-IOSLPCCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid
• IUPAC Traditional name: α,β-methylene adp
• Synonyms: α,β-Methyleneadenosine 5′-diphosphate; ADP[α,β-CH2]; AMP-CP; Adenosine 5′-(α,β-methylene)diphosphate

Database IDs

• CAS Number: 3768-14-7
• EC Number: 223-194-0
• MDL Number: MFCD00042991
• Beilstein Number: 633678
• PubChem SID: 162227601; 24896872
• PubChem CID: 92199

CALCULATED PROPERTIES

• Acid pKa: 0.98112744
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -8.182416
• LogD (pH = 7.4): -8.16192
• Log P: -5.8846297
• Molar Refractivity: 87.2951 cm^3
• Polarizability: 34.85279 Å^3
• Polar Surface Area: 223.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C11H17N5O9P2

DETAILS

Sigma Aldrich - M3763

Application
Adenosine 5′-(α,β-methylene)diphosphate (AMP-CP) is a CD73 inhibitor and is used to study adenosinergic signaling regulation via CD73/ecto-5′-nucleotidase.
Reconstitution
soluble in water up to Approx. 50 mg/ml with heating

Sigma Aldrich - 01920

Other Notes
Powerful inhibitor of 5′-nucleotidase from rat heart membranes1; Useful tool in kinetic studies with 5′-nucleotidase2