NAD   Click here for help

GtoPdb Ligand ID: 2451

Synonyms: NAD+
PDB Ligand
Compound class: Metabolite

NAD is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
aldehyde dehydrogenase 2 family member 1.2.1.3 an aldehyde + H2O + NAD = a carboxylate + 2H+ + NADH
aldehyde dehydrogenase 5 family member A1 1.2.1.24 4-Oxobutanoate + NAD + H2O = succinic acid + NADH + 2H+
4-hydroxy-trans-2-nonenal + NAD + H2O = 4-hydroxy-trans-2-nonenoate + NADH + 2H+
aldehyde dehydrogenase 9 family member A1 1.2.1.19, 1.2.1.3, 1.2.1.47 4-Aminobutanal + NAD + H2O = GABA + NADH + H+

an aldehyde + H2O + NAD = a carboxylate + 2H+ + NADH

4-Trimethylammoniobutanal + NAD + H2O = 4-trimethylammoniobutanoate + NADPH + 2H+
Cofactor in Enzyme Reactions
Enzyme Reference
aldehyde dehydrogenase 5 family member A1
aldehyde dehydrogenase 9 family member A1
delta 4-desaturase, sphingolipid 1
delta 4-desaturase, sphingolipid 2
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
P2Y11 receptor Hs Agonist Full agonist - - - 3
⤷ [3]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPM2 Ligand is endogenous in the given species Hs Activator Agonist - - 3x10-4 - 1x10-3 1-2,4-5
⤷ Conc range: 3x10-4 - 1x10-3 M [1-2,4-5]
Voltage: -60.0 mV