NAD   Click here for help

GtoPdb Ligand ID: 2451

Synonyms: NAD+
PDB Ligand
Compound class: Metabolite
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key BAWFJGJZGIEFAR-NNYOXOHSSA-N
References
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]