disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

• ChemBase ID: 102867
• Molecular Formular: C10H12N5Na2O7P
• Molecular Mass: 391.184881
• Monoisotopic Mass: 391.02697294
• SMILES: [Na+].[Na+].[O-]P(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(ncnc23)N)[C@H](O)[C@@H]1O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2N)COP(=O)([O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C10H14N5O7P.2Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20;;/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1
• InChIKey: QGXLVXZRPRRCRP-IDIVVRGQSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• IUPAC Traditional name: disodium adenosine-5-monophosphate(2-)
• Synonyms: Adenosine-5'-Monophosphoric Acid Disodium Salt; ADENOSINE-5'-MONOPHOSPHATE DISODIUM SALT; A-5′-P; Adenosine 5′-monophosphate sodium salt; AMP; 5'-Adenylic acid; ADENOSINE-5'-MONOPHOSPHATE DISODIUM SALT HYDRATE; 5'-Adenylic Acid Sodium Salt; 5'-Adenylic Acid Disodium Salt; 5'-AMP Disodium Salt; AMP Disodium Salt; Adenosine 5'-phosphate Disodium Salt; Adenylic Acid Disodium Salt; Disodium 5'-AMP; Disodium 9-(β-D-Ribofuranosyl)adenine 5'-Monophosphate; Disodium AMP; Disodium Adenosine 5'-Phosphate; Disodium Adenylate; Adenosine 5'-Monophosphate Disodium Salt; 5'-Adenylic acid disodium salt; 5′-腺苷酸; 腺苷-5'-单磷酸 钠盐

Database IDs

• CAS Number: 149022-20-8; 4578-31-8
• EC Number: 224-961-2
• MDL Number: MFCD00065023
• PubChem SID: 24890583; 24890891; 162089081
• PubChem CID: 20712

CALCULATED PROPERTIES

• Acid pKa: 1.2246295
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -4.7514725
• LogD (pH = 7.4): -5.7464666
• Log P: -5.1917415
• Molar Refractivity: 71.8251 cm^3
• Polarizability: 28.853146 Å^3
• Polar Surface Area: 191.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble; Methanol; Water
• Apperance: crystalline; White Solid
• Melting Point: > 300°C; 232-235°C

Safety Information

• Storage Condition: 0°C; Refrigerator
• RTECS: AU7481600; AU7490000
• 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: ≥99%; 95+%; 99-100%
• Suitability: cell culture tested
• Biological Source: from equine muscle; from yeast
• Quality Level: PREMIUM

DETAILS

MP Biomedicals - 02104826

Disodium Salt
Crystalline
Purity: 99-100%

MP Biomedicals - 02150264

From Yeast
Disodium Salt
Crystalline
Purity: 99-100%

Sigma Aldrich - A1752

Application
Adenosine 5′-monophosphate (5′-AMP) has many uses in nature. 5′-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase (AMPK).

Toronto Research Chemicals - A281790

Adenosine monophosphate is useful for skin rejuvenation in dermatology and aesthetic dermatology.

REFERENCES

• Watanabe, M., et al.: Arch. Dermatol., 127, 1689 (1991)
• Engelke, M., et al.: Br. J. Dermatol., 137, 219 (1991)