NADH

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H29N7O14P2
Molecular Weight	665.441
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=CN(C=CC1)[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N4C=NC5=C4N=CN=C5N)[C@@H](O)[C@H]2O

InChI

InChIKey=BOPGDPNILDQYTO-NNYOXOHSSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H29N7O14P2
Molecular Weight	665.441
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/books/NBK26882/ | https://www.webmd.com/vitamins/ai/ingredientmono-1016/nadh | https://www.ncbi.nlm.nih.gov/pubmed/24559077 | https://www.ncbi.nlm.nih.gov/pubmed/28111818 |

Nicotinamide adenine nucleotide (NAD) is a cofactor found in all living cells. It exists in oxidized form (NAD+) and reduced form (NADH). NADH is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). NADH supplements are used for improving mental clarity, alertness, concentration, and memory; as well as for treating Alzheimer’s disease and dementia. Because of its role in energy production, NADH is also used for improving athletic performance and treating chronic fatigue syndrome (CFS). Some people use NADH for treating high blood pressure, high cholesterol, jet lag, depression, and Parkinson’s disease; opposing alcohol’s effects on the liver; reducing signs of aging; protecting against the side effects of an AIDS drug called zidovudine (AZT).

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NAD-dependent deacetylase sirtuin 1 16 Target ID: CHEMBL4506 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21528845	Substrate 661
L-lactate dehydrogenase A chain 4 Target ID: CHEMBL4835 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8308865	Substrate 661
Alcohol dehydrogenase alpha chain 2 Target ID: CHEMBL1970 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8308865	Substrate 661
cell redox homeostasis 5 Target ID: GO:0045454 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28648096 \| https://www.leebio.com/product/1094/beta-nicotinamide-adenine-dinucleotide-nadh-reduced-form-disodium-salt-943-20	Modulator 828

PubMed

Title	Date	PubMed
Structure of lactate dehydrogenase inhibitor generated from coenzyme.	1979 Apr 3	218616
Solubilization, purification, and characterization of a truncated form of rat hepatic squalene synthetase.	1992 Apr 25	1569107
RNA-stimulated NTPase activity associated with yellow fever virus NS3 protein expressed in bacteria.	1993 Feb	8380474
Adp-ribosyl cyclase and cyclic ADP-ribose hydrolase act as a redox sensor. a primary role for cyclic ADP-ribose in hypoxic pulmonary vasoconstriction.	2001 Apr 6	11116136
Bcl-xL promotes the open configuration of the voltage-dependent anion channel and metabolite passage through the outer mitochondrial membrane.	2001 Jun 1	11259441
Voltammetric biosensors for the determination of formate and glucose-6-phosphate based on the measurement of dehydrogenase-generated NADH and NADPH.	2001 May	11340000
Role of redox potential of hemoglobin-based oxygen carriers on methemoglobin reduction by plasma components.	2002 Jan	12000225
Dynamics of nucleotides in VDAC channels: structure-specific noise generation.	2002 Jan	11751308
Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease.	2003 Apr	12648681
Cytoprotection of pyruvic acid and reduced beta-nicotinamide adenine dinucleotide against hydrogen peroxide toxicity in neuroblastoma cells.	2003 May	12716024
Reversible, electrochemical interconversion of NADH and NAD+ by the catalytic (Ilambda) subcomplex of mitochondrial NADH:ubiquinone oxidoreductase (complex I).	2003 May 21	12785808
Mitochondrial NADH redox state, monitoring discovery and deployment in tissue.	2004	15130749
Trichomonas hydrogenosomes contain the NADH dehydrogenase module of mitochondrial complex I.	2004 Dec 2	15577909
New photoproducts from irradiation of NADH with near-UV light.	2004 Oct	17191792
Role of inhibitor aliphatic chain in the thermodynamics of inhibitor binding to Escherichia coli enoyl-ACP reductase and the Phe203Leu mutant: a proposed mechanism for drug resistance.	2004 Oct 26	15491144
Catalase-peroxidases (KatG) exhibit NADH oxidase activity.	2004 Oct 8	15280362
Biomimetics with a self-assembled monolayer of catalytically active tethered isoalloxazine on Au.	2005 Aug 16	16089399
Canal wall reconstruction and mastoid obliteration with composite multi-fractured osteoperiosteal flap.	2006 Dec	17006636
NADPH- diaphorase positive cardiac neurons in the atria of mice. A morphoquantitative study.	2006 Feb 2	16451738
High-resolution intravital NADH fluorescence microscopy allows measurements of tissue bioenergetics in rat ileal mucosa.	2006 Jan	16393945
Superoxide anion is elevated in sympathetic neurons in DOCA-salt hypertension via activation of NADPH oxidase.	2006 Mar	16214837
Temperature dependence for fluorescence of beta-NADH in glycerol/water solution and in trehalose/sucrose glass.	2007 Jan	17171438
NAD+ metabolism in health and disease.	2007 Jan	17161604
The power to reduce: pyridine nucleotides--small molecules with a multitude of functions.	2007 Mar 1	17295611
Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery.	2007 May	17465726
Modulation of vascular reactivity in normal, hypertensive and diabetic rat aortae by a non-antioxidant flavonoid.	2007 May	17317209
Effect of water activity on inactivation of Listeria monocytogenes and lactate dehydrogenase during high pressure processing.	2008 May 10	18403036
Pharmacologic inhibition of squalene synthase and other downstream enzymes of the cholesterol synthesis pathway: a new therapeutic approach to treatment of hypercholesterolemia.	2009 Mar-Apr	19367148
Structural and mechanistic roles of three consecutive Pro residues of porcine NADH-cytochrome b(5) reductase for the binding of beta-NADH.	2009 Oct	19716516
Structural and redox behavior of OxyVita, a zero-linked polymeric hemoglobin: comparison with natural acellular polymeric hemoglobins.	2010 Apr	20196683

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:56:42 UTC 2023` Edited by `admin` on `Sat Dec 16 01:56:42 UTC 2023`
Record UNII	4J24DQ0916
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NADH	Locators: WHO-DD Sources:

Common Name

English

NAD REDUCED FORM

Common Name

English

NICOTINAMIDE-ADENINE DINUCLEOTIDE, REDUCED

Common Name

English

NAD REDUCED FORM [MI]

Common Name

English

REDUCED NICOTINAMIDE-ADENINE DINUCLEOTIDE

Common Name

English

ADENOSINE 5'-(TRIHYDROGEN DIPHOSPHATE), P'->5'-ESTER WITH 1,4-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-3-PYRIDINECARBOXAMIDE

Common Name

English

REDUCED NICOTINAMIDE ADENINE DIPHOSPHATE

Common Name

English

NADH [WHO-DD]

Common Name

English

Classification Tree Code System Code

DSLD

2235 (Number of products:5)