CAS 606-68-8|Nadide|nicotinamide adenine dinucleotide reduced|Nicotinamide adenine dinucleotide|Nicotinaminde-Adenine-Dinucleotide|NAD-reduced|[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxola...

General Information

Structure

Molecular Formula

C₂₁H₂₉N₇O₁₄P₂

Molecular Mass

665.440982

Exact Mass

665.1247719

Charge

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

Canonic Smiles

O[C@@H]1[C@H](O)[C@H](O[C@H]1N1C=CCC(=C1)C(=O)N)CO[P@](=O)(O[P@](=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)O)O

Isomeric Smiles

[P@](=O)(OC[C@H]1O[C@@H](n2c3ncnc(N)c3nc2)[C@H](O)[C@@H]1O)(O[P@@](=O)(OC[C@H]1O[C@@H](N2C=C(CC=C2)C(=O)N)[C@H](O)[C@@H]1O)O)O

Calculated Properties

JChem

Acid pKa

-7.028098

H Acceptors

H Donor

LogD (pH = 5.5)

-8.260936

LogD (pH = 7.4)

-8.57728

Log P

-6.471756

Molar Refractivity

142.9997

Polarizability

56.70642

Polar Surface Area

317.62

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

-1.45

LOG S

-2.35

Solubility (Water)

2.95e+00 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

Nadide

Synonyms

nicotinamide adenine dinucleotide reducedNicotinamide adenine dinucleotideNicotinaminde-Adenine-DinucleotideNAD-reduceddiphosphopyridine nucleotide reducedbeta-NADHDPN+NADHCozymase I, reducedCoenzyme I, reduceddihydronicotinamide adenine dinucleotideNADH+H+NAD+DPNNADH2beta-DPNHdihydrodiphosphopyridine nucleotideDPNHDiphosphopyridine nucleotide

IUPAC Traditional name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid

IUPAC name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Names and Identifiers

Registration numbers

PubChem CID

439153

CAS Number

606-68-8

PubChem SID

46504879160963506

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-5.1

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00157

Drug Groups

approved; nutraceutical

Description

NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It 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). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed)

Indication

Some evidence suggests that NADH might be useful in treating Parkinson's disease, chronic fatigue syndrome, Alzheimer's disease and cardiovascular disease.

Pharmacology

A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It 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). The action of supplemental NADH is unclear. Oral NADH supplementation has been used to combat simple fatigue as well as such mysterious and energy-sapping disorders as chronic fatigue syndrome and fibromyalgia. Researchers are also studying the value of NADH supplements for improving mental function in people with Alzheimer's disease, and minimizing physical disability and relieving depression in people with Parkinson's disease. Some healthy individuals also take NADH supplements orally to improve concentration and memory capacity, as well as to increase athletic endurance. However, to date there have been no published studies to indicate that using NADH is in any way effective or safe for these purposes.

Toxicity

No reports of overdose, however, high doses of NADH (10 mg a day or more) may cause jitteriness, anxiety, and insomnia.

Affected Organisms

Humans and other mammals

Absorption

Unclear how much of an administered dose is absorbed.

References

• [Link]

• Belenky P, Bogan KL, Brenner C: NAD+ metabolism in health and disease. Trends Biochem Sci. 2007 Jan;32(1):12-9. Epub 2006 Dec 11. [Pubmed]

• Pollak N, Dolle C, Ziegler M: The power to reduce: pyridine nucleotides--small molecules with a multitude of functions. Biochem J. 2007 Mar 1;402(2):205-18. [Pubmed]

• Khan JA, Forouhar F, Tao X, Tong L: Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery. Expert Opin Ther Targets. 2007 May;11(5):695-705. [Pubmed]

• Lin SJ, Guarente L: Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease. Curr Opin Cell Biol. 2003 Apr;15(2):241-6. [Pubmed]

• Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7. [Pubmed]

External Links

• [Wikipedia]

• [PDRhealth]

Molecule Details

References

PubChem Literature

From Data Sources

• Belenky P, Bogan KL, Brenner C: NAD+ metabolism in health and disease. Trends Biochem Sci. 2007 Jan;32(1):12-9. Epub 2006 Dec 11. Pubmed

• Link

• Lin SJ, Guarente L: Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease. Curr Opin Cell Biol. 2003 Apr;15(2):241-6. Pubmed

• Pollak N, Dolle C, Ziegler M: The power to reduce: pyridine nucleotides--small molecules with a multitude of functions. Biochem J. 2007 Mar 1;402(2):205-18. Pubmed

• Khan JA, Forouhar F, Tao X, Tong L: Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery. Expert Opin Ther Targets. 2007 May;11(5):695-705. Pubmed

• Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Brand Name

• Synonyms

• IUPAC Traditional name

• IUPAC name

Registration numbers

• PubChem CID

• CAS Number

• PubChem SID

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

IUPAC Traditional name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid

IUPAC name

PubChem SID

46504879160963506

Physical Property

Hydrophobicity(logP)

-5.1

DrugBank

DB00157

Drug Groups

approved; nutraceutical

Description

Indication

Some evidence suggests that NADH might be useful in treating Parkinson's disease, chronic fatigue syndrome, Alzheimer's disease and cardiovascular disease.

Pharmacology

Toxicity

No reports of overdose, however, high doses of NADH (10 mg a day or more) may cause jitteriness, anxiety, and insomnia.

Affected Organisms

Humans and other mammals

Absorption

Unclear how much of an administered dose is absorbed.

References

• [Link]

• Belenky P, Bogan KL, Brenner C: NAD+ metabolism in health and disease. Trends Biochem Sci. 2007 Jan;32(1):12-9. Epub 2006 Dec 11. [Pubmed]

• Pollak N, Dolle C, Ziegler M: The power to reduce: pyridine nucleotides--small molecules with a multitude of functions. Biochem J. 2007 Mar 1;402(2):205-18. [Pubmed]

• Khan JA, Forouhar F, Tao X, Tong L: Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery. Expert Opin Ther Targets. 2007 May;11(5):695-705. [Pubmed]

• Lin SJ, Guarente L: Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease. Curr Opin Cell Biol. 2003 Apr;15(2):241-6. [Pubmed]

• Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7. [Pubmed]

External Links

• [Wikipedia]

• [PDRhealth]

From Data Sources

• Belenky P, Bogan KL, Brenner C: NAD+ metabolism in health and disease. Trends Biochem Sci. 2007 Jan;32(1):12-9. Epub 2006 Dec 11. Pubmed

• Link

• Lin SJ, Guarente L: Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease. Curr Opin Cell Biol. 2003 Apr;15(2):241-6. Pubmed

• Pollak N, Dolle C, Ziegler M: The power to reduce: pyridine nucleotides--small molecules with a multitude of functions. Biochem J. 2007 Mar 1;402(2):205-18. Pubmed

• Khan JA, Forouhar F, Tao X, Tong L: Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery. Expert Opin Ther Targets. 2007 May;11(5):695-705. Pubmed

• Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7. Pubmed

Molecule

ID:43