NADH (C21H29N7O14P2): structure, properties and hazards

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-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
Synonyms: reduced NAD, dihydronicotinamide adenine dinucleotide, NADH2
+ 35 more
DPNH, beta-NADH, 1,4-Dihydronicotinamide adenine dinucleotide, Reduced nicotinamide adenine diphosphate, Reduced nicotinamide-adenine dinucleotide, Reduced Nicotinamide Adenine Dinucleotide, [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate, 4J24DQ0916, Nicotinamide-adenine dinucleotide, reduced, nicotinamide adenine dinucleotide (reduced), CHEBI:16908, DTXSID30889320, [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid, Adenosine 5'-(trihydrogen diphosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide, NAD reduced, (((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)((((2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy))phosphinic acid, (((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl hydrogen phosphate, ((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl (((2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) hydrogen phosphate, [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate, RefChem:552993, DTXCID301028583, 200-393-0, beta-DPNH, Dihydrocozymase, Coenzyme I, reduced, Cozymase I, reduced, Dihydrocodehydrogenase I, Reduced codehydrogenase I, Dihydronicotinamide mononucleotide, Reduced diphosphopyridine nucleotide, Codehydrase I, reduced, Codehydrogenase I, reduced, NAD reduced form, Dihydronicotinamide-adenine dinucleotide, Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide
Molecular formula: C₂₁H₂₉N₇O₁₄P₂
Empirical formula: C₂₁H₂₉N₇O₁₄P₂
Molecular weight: 665.4 g/mol
Exact mass: 665.12477
CAS number: 58-68-4
PubChem CID: 439153
Canonical SMILES: C1C=CN(C=C1C(=O)N)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
Isomeric SMILES: C1C=CN(C=C1C(=O)N)[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
InChI: InChI=1S/C21H29N7O14P2/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/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChIKey: BOPGDPNILDQYTO-NNYOXOHSSA-N
Molfile

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

Calculated

Heavy atoms: 44
Rings: 5
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.52
H-bond donors: 8
H-bond acceptors: 17 computed here · PubChem 19
Rotatable bonds: 11
TPSA (Å²): 317.6 computed here · PubChem 318
Formal charge: 0
XLogP3: -5.7 PubChem
Complexity: 1230 PubChem
Stereocenters: 8 defined, 2 undefinedCIP: C7: R · C9: R · P12: undefined · P16: undefined · C21: R · C23: R · C34: R · C36: S · C38: S · C40: 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

C37.90%
H4.39%
N14.73%
O33.66%
P9.31%

Isotope pattern

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: -2.69 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.7 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 5.27 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 665.45
log P ≤ 5 (Crippen): -2.69
H-bond donors ≤ 5: 8
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

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: AiFChem, an XtalPi Company, RR Scientific, BOC Sciences.

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]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.

Similar structures

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.