5'-adenylic acid

5'-adenylic acid

formula | C_10H_14N_5O_7P name | 5'-adenylic acid IUPAC name | [(2R, 3R, 4S, 5S)-5-(6-aminopurin-9-yl)-3, 4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid alternate names | adenosine 5'-(dihydrogen phosphate) | adenosine 5'-monophosphate | adenosine monophosphate mass fractions | C (carbon) 34.6% | H (hydrogen) 4.06% | N (nitrogen) 20.2% | O (oxygen) 32.3% | P (phosphorus) 8.92%

Draw the Lewis structure of 5'-adenylic acid. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), oxygen (n_O, val = 6), and phosphorus (n_P, val = 5) atoms: 10 n_C, val + 14 n_H, val + 5 n_N, val + 7 n_O, val + n_P, val = 126 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), oxygen (n_O, full = 8), and phosphorus (n_P, full = 8): 10 n_C, full + 14 n_H, full + 5 n_N, full + 7 n_O, full + n_P, full = 212 Subtracting these two numbers shows that 212 - 126 = 86 bonding electrons are needed. Each bond has two electrons, so in addition to the 39 bonds already present in the diagram we expect to add 4 bonds. To minimize formal charge oxygen wants 2 bonds, nitrogen wants 3 bonds, and carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Add 4 bonds by pairing electrons between adjacent highlighted atoms. Additionally, atoms with large electronegativities can minimize their formal charge by forcing atoms with smaller electronegativities on period 3 or higher to expand their valence shells. The electronegativities of the atoms are 2.19 (phosphorus), 2.20 (hydrogen), 2.55 (carbon), 3.04 (nitrogen), and 3.44 (oxygen). Because the electronegativity of phosphorus is smaller than the electronegativity of oxygen, expand the valence shell of phosphorus to 5 bonds. Therefore we add a total of 5 bonds to the diagram. Note that the six atom ring is aromatic, so that the single and double bonds may be rearranged: Answer: | |

3D structure

molar mass | 347.22 g/mol phase | solid (at STP) melting point | 199 °C solubility in water | very soluble

experimental LogP hydrophobicity | -3.1 predicted LogP hydrophobicity | -3.12 predicted LogS | -2.02

approval status | approved | nutraceutical | small molecule drug categories | dietary supplement | micronutrient

brand names | adenovite | cardiomone | lycedan | My-B-den | phosaden | phosphaden

CAS number | 61-19-8 Beilstein number | 54612 PubChem CID number | 638042 PubChem SID number | 3322 SMILES identifier | C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)O)O)O InChI identifier | InChI=1/C10H14N5O7P/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)/t4-, 6+, 7+, 10+/m1/s1/f/h18-19H, 11H2 InChI key | UDMBCSSLTHHNCD-WLZLVAIBDR EU number | 200-500-0 RTECS number | AU7480500 NSC number | 20264

NFPA label

NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0

RTECS classes | mutagen | reproductive effector