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NAD+

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C21H27N7O14P2 · 663.4 g/mol

IUPAC name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

Also called nicotinamide adenine dinucleotide, NAD, DPN, diphosphopyridine nucleotide, coenzyme I

VitaminsNucleic acid parts
Open in Athanor
The structure of NAD+
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Synonyms
nicotinamide adenine dinucleotide, NAD, DPN
+ 38 more

diphosphopyridine nucleotide, coenzyme I, nadide, beta-NAD, Codehydrase I, Codehydrogenase I, Cozymase I, beta-Diphosphopyridine nucleotide, Enzopride, COZYMASE, Nadidum, Nicotinamide-adenine dinucleotide, codehydrogenase, Nadida, Pyridine, nucleotide diphosphate, Adenine-nicotinamide dinucleotide, Nadida [INN-Spanish], Nicotineamide adenine dinucleotide, Nadidum [INN-Latin], .beta.-NAD, Nadide [USAN:INN:BAN:JAN], EINECS 200-184-4, NSC 20272, BRN 3584133, 0U46U6E8UK, NADIDE [USAN], NADIDUM [HPUS], NADIDE [INN], NADIDE [JAN], NADIDE [WHO-DD], NADIDE [MART.], NSC-20272, NAD(SUP +), 3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide, 5'-ester with adenosine 5'-pyrophosphate, inner salt, Nicotinamide Adinine Dinucleotide, EC 200-184-4, 5-26-16-00399 (Beilstein Handbook Reference), Adenosine 5'-(trihydrogen diphosphate), P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium hydroxide, inner salt

Molecular formula
C21H27N7O14P2
Empirical formula
C21H27N7O14P2
Molecular weight
663.4 g/mol
Exact mass
663.10912
CAS number
53-84-9
PubChem CID
5892
Canonical SMILES
C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)C(=O)N
Isomeric SMILES
C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)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
InChIKey
BAWFJGJZGIEFAR-NNYOXOHSSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
44
Rings
5
Aromatic rings
3
Fraction sp³ carbons (Fsp3)
0.48
H-bond donors
7
H-bond acceptors
17 computed here · PubChem 18
Rotatable bonds
11
TPSA (Ų)
321.1 computed here · PubChem 321
Formal charge
0
XLogP3
-6 PubChem
Complexity
1120 PubChem
Stereocenters
8 defined, 2 undefinedCIP: C10: R · C12: R · P15: undefined · P19: undefined · C24: R · C26: R · C37: R · C39: S · C41: S · C43: R
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C38.02%
  • H4.10%
  • N14.78%
  • O33.76%
  • P9.34%

Isotope pattern

100%663.10926%664.1126.2%665.1141.0%666.116667.119

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
-3.65 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-1.18 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
5.34 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 663.43
  • log P ≤ 5 (Crippen): -3.65
  • H-bond donors ≤ 5: 7
  • H-bond acceptors ≤ 10: 17

Breaks 3 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

This chemical does not meet GHS hazard criteria for 99.1% (114 of 115) of all reports.[1]

Safety data sheets on the supplier’s page: Aladdin Scientific, AKos Consulting & Solutions, Biorbyt.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  5. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  6. ·Literature on PubChem

Data last updated 2026-10-14.