NAD   Click here for help

GtoPdb Ligand ID: 2451

Synonyms: NAD+
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 19
Hydrogen bond donors 7
Rotatable bonds 11
Topological polar surface area 340.71
Molecular weight 663.11
XLogP -4.2
No. Lipinski's rules broken 3
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Canonical SMILES OC1C(COP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2ncnc3N)O)[O-])OC(C1O)[n+]1cccc(c1)C(=O)N
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2ncnc3N)O)[O-])O[C@H]([C@@H]1O)[n+]1cccc(c1)C(=O)N
InChI InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
1. Hara Y, Wakamori M, Ishii M, Maeno E, Nishida M, Yoshida T, Yamada H, Shimizu S, Mori E, Kudoh J et al.. (2002)
LTRPC2 Ca2+-permeable channel activated by changes in redox status confers susceptibility to cell death.
Mol Cell, 9 (1): 163-73. [PMID:11804595]
2. Heiner I, Eisfeld J, Halaszovich CR, Wehage E, Jüngling E, Zitt C, Lückhoff A. (2003)
Expression profile of the transient receptor potential (TRP) family in neutrophil granulocytes: evidence for currents through long TRP channel 2 induced by ADP-ribose and NAD.
Biochem J, 371 (Pt 3): 1045-53. [PMID:12564954]
3. Moreschi I, Bruzzone S, Nicholas RA, Fruscione F, Sturla L, Benvenuto F, Usai C, Meis S, Kassack MU, Zocchi E et al.. (2006)
Extracellular NAD+ is an agonist of the human P2Y11 purinergic receptor in human granulocytes.
J Biol Chem, 281 (42): 31419-29. [PMID:16926152]
4. Sano Y, Inamura K, Miyake A, Mochizuki S, Yokoi H, Matsushime H, Furuichi K. (2001)
Immunocyte Ca2+ influx system mediated by LTRPC2.
Science, 293 (5533): 1327-30. [PMID:11509734]
5. Togashi K, Hara Y, Tominaga T, Higashi T, Konishi Y, Mori Y, Tominaga M. (2006)
TRPM2 activation by cyclic ADP-ribose at body temperature is involved in insulin secretion.
EMBO J, 25 (9): 1804-15. [PMID:16601673]