ChemFOnt: Showing chemical card for 1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid (CFc000136310)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 22:09:46 UTC

Chemfont ID

CFc000136310

Molecule Identification

Common Name

1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid

Definition

NADH, also known as DPNH or b-nadh, belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. NADH is a strong basic compound (based on its pKa). NADH exists in all living species, ranging from bacteria to humans. A coenzyme found in all living cells; consists of two nucleotides joined through their 5'-phosphate groups, with one nucleotide containing an adenine base and the other containing nicotinamide. In humans, NADH is involved in doxorubicin metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-DIHYDRONICOTINAMIDE adenine dinucleotide	ChEBI
DPNH	ChEBI
Nicotinamide adenine dinucleotide (reduced)	ChEBI
Reduced nicotinamide adenine dinucleotide	ChEBI
b-DPNH	HMDB
b-NADH	HMDB
beta-DPNH	HMDB
beta-NADH	HMDB
Dihydrocodehydrogenase I	HMDB
Dihydrocozymase	HMDB
Dihydronicotinamide adenine dinucleotide	HMDB
Dihydronicotinamide mononucleotide	HMDB
ENADA	HMDB
NADH2	HMDB
Reduced codehydrogenase I	HMDB
Reduced diphosphopyridine nucleotide	HMDB
Reduced nicotinamide adenine diphosphate	HMDB
Reduced nicotinamide-adenine dinucleotide	HMDB
Nadide	HMDB
Coenzyme I	HMDB
DPN	HMDB
Diphosphopyridine nucleotide	HMDB
Nicotinamide adenine dinucleotide	HMDB
Nicotinamide-adenine dinucleotide	HMDB
NAD	HMDB
Nucleotide, diphosphopyridine	HMDB
Adenine dinucleotide, dihydronicotinamide	HMDB
Dinucleotide, dihydronicotinamide adenine	HMDB
Dinucleotide, nicotinamide-adenine	HMDB

Chemical Formula

C₂₁H₂₉N₇O₁₄P₂

Average Molecular Weight

665.441

Monoisotopic Molecular Weight

665.124771695

IUPAC Name

[({[(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

Traditional Name

NADH

CAS Registry Number

58-68-4

SMILES

NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

InChI Identifier

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

InChI Key

BOPGDPNILDQYTO-NNYOXOHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
N-substituted nicotinamide
Organic pyrophosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Dihydropyridine
Aminopyrimidine
Pyrimidine
Imidolactam
Monosaccharide
N-substituted imidazole
Alkyl phosphate
Phosphoric acid ester
Hydropyridine
Organic phosphoric acid derivative
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Vinylogous amide
Azole
Amino acid or derivatives
Primary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Enamine
Azacycle
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Primary amine
Amine
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

NAD (CHEBI:16908 )
NAD(P)H (CHEBI:16908 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.95 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5.9	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	317.62 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	143 m³·mol⁻¹	ChemAxon
Polarizability	57.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001487

DrugBank ID

DB00157

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Nicotinamide_adenine_dinucleotide

METLIN ID

3687

PubChem Compound

439153

PDB ID

Not Available

ChEBI ID

16908

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid (CFc000136310)

MOL for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

3D MOL for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

3D SDF for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

3D-SDF for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

PDB for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

3D PDB for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

SMILES for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

INCHI for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

Structure for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)

3D Structure for CFc000136310 (1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid)