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beta-Nicotinamide adenine dinucleotide

HCID 925
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
53-84-9
Standard SMILES
NC(=O)c1ccc[n+](C2OC(COP(=O)([O-])OP(=O)(O)OCC3OC(n4cnc5c(N)ncnc54)C(O)C3O)C(O)C2O)c1
InChIKey
BAWFJGJZGIEFAR-UHFFFAOYSA-N
Molecular formula
C21H27N7O14P2
Average molar mass
663.4 g/mol
Monoisotopic mass
663.10912256

Overview

See also: Nadide (annotation moved to).

Names & identifiers

Preferred name
beta-Nicotinamide adenine dinucleotide
IUPAC
[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
English name
β-Nicotinamide adenine dinucleotide
Molecular formula
C21H27N7O14P2
Molecular weight
663.43

Names & synonyms

beta-nicotinamide adenine dinucleotideBeta-diphosphopyridineEndopridebeta-DPN;beta-NAD;beta-Nicotinamide Adenine DinucleotideNSC20272NAD+ (?-DPN)SCHEMBL4363695SCHEMBL32682194b-Nicotinamide adenine dinucleotideEC-Nicotinamide adenine dinucleotide|?-Nicotinamide adenine dinucleotides2518
Show more names
NADβ-NADDPNB-NADbeta-Diphosphopyridine nucleotideβ-nicotinamide adenine dinucleotide hydratecozymaseibeta-NAD
AKOS026750156DA-35035DB-055710NAD (beta-Nicotinamide adenine dinucleotide) FGAdenosine 5'-(trihydrogen diphosphate), hydroxide, inner saltNAD (beta-Nicotinamide adenine dinucleotide) (C21H27N7O14P2)3-Carbamoyl-1.beta.-D-ribofuranosylpyridinium hydroxide, inner salta-Nicotinamide adenine dinucleotide from Saccharomyces cerevisiae

Database identifiers

CAS

Properties

Computed structural properties

XLogP
-6
Topological polar surface area
321 Ų
Hydrogen bond donors
7
Hydrogen bond acceptors
18
Rotatable bonds
11
Heavy atoms
44
Formal charge
0
Complexity
1,120

Physicochemical properties

Melting point
140 · 140-142 °C (decomp)
alpha
20 · D20 -31.5° (c = 1.2 in water)
bulk density
200 · 200-300kg/m3
storage temp.
-20 °C · -20°C
solubility
2 O: · H2O: 50 mg/mL
form
Powder
pka
5.25 · 5.25
color
White
PH
3 · ~3.0 (50mg/mL in water)
Odor
Odorless
biological source
yeast
Water Solubility
50 mg/ml · Soluble in water at 50mg/ml
λmax
260 nm · 260 nm
Merck
14 · 14,6344
BRN
3584133 · 3584133
Stability
Stable. Hygroscopic. Incompatible with strong oxidizing agents.
Major Application
metabolomics

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
tsca
TSCA listed
rtecs
UU3450000
hs_code
29349990
risk_code
36-68/20/21/22-20/21/22-40-22
Signal word
Warning
Symbol(GHS)
GHS08
hazard_code
Xn,F,Xi
safety_code
36-26-36/37-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H371
REACH Registrations
Active
Precautionary statements
P260-P264-P270-P308+P311-P405-P501

Chemistry & industry

Applications · 4 items

Descriptionβ-Nicotinamide adenine dinucleotide (NAD+) plays a major role in metabolism as a cofactor and mobile electron acceptor. NAD+ is a required oxidizing cosubstrate for many enzymes. It is reduced to NADH (Cat# N-035) which carries electrons to the electron transport chain for subsequent oxidative phorphorylation and ATP production. NAD+ is capable of donating ADP-ribose moieties to a protein, producing nicotinamide in the process. Sirtuin enzymes use NAD+ as a substrate to deacetylate proteins and direct activity between the nucleus and mitochondria. NAD+ is regenerated by fermentation and by oxidative phosphorylation.

Historyβ-Nicotinamide adenine dinucleotide was first discovered by British biochemists Arthur Harden and William John Young in 1906. They observed that the addition of boiled and filtered yeast extract significantly increased the rate of alcoholic fermentation in unboiled yeast extracts. They named the unidentified factor responsible for this effect a coferment. By extensively purifying it from yeast extracts, Hans von Euler-Chelpin identified this heat-stable factor as a nucleotide sugar phosphate. In 1936, German scientist Otto Heinrich Warburg demonstrated the role of this nucleotide coenzyme in hydride transfer and determined the nicotinamide portion as the site of redox reactions. Vitamin precursors of NAD+ were first identified in 1938, when Conrad Elvehjem showed that liver has an "anti-black tongue" activity in the form of nicotinamide. Then, in 1939, he provided the first strong evidence that niacin is used to synthesize NAD+.

Usesβ-Nicotinamide Adenine Dinucleotide is a coeznyme consisting of an adenine base and a nicotinamide base connected by a pair of bridging phosphate group. β-Nicotinamide Adenine Dinucleotide acts as a c oenzyme in redox reactions, as a donor of ADP-ribose moieties in ADP-ribosylation reactions and also as a precursor of the second messenger molecule cyclic ADP-ribose. β-Nicotinamide Adenine Dinucleot ide also acts as a substrate for bacterial DNA ligases and a group of enzymes called sirtuins that use NAD+ to remove acetyl groups from proteins.

General Descriptionβ-Nicotinamide adenine dinucleotide (NAD) is a ubiquitously found electron carrier and a cofactor. NAD+ contains an adenylic acid and a nicotinamide-5′-ribonucleotide group linked together by a pyrophosphate moiety. In NAD+ complexes, the enzyme-cofactor interactions are highly conserved.

Upstream & downstream products

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
53-84-9
PubChem CID
925
Cosmetics Ingredients Functions
SKIN CONDITIONING
InChIKey
BAWFJGJZGIEFAR-WWRWIPRPSA-N
SMILES
NC1=NC=NC2=C1N=CN2.O[C@@H]3[C@@H](COP(O)(OP(OC[C@@H](O4)[C@@H](O)[C@@H](O)[C@H]4[N+]5=CC=CC(C(N)=O)=C5)([O-])=O)=O)OC[C@@H]3O
FDA UNII
0 U46U6E8UK · 0U46U6E8UK
EPA Substance Registry System
5 · Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt (53-84-9)
UNSPSC Code
41106305 · 41106305
NACRES
21 · NB.21
Symbol(GHS)
8 · GHS08
Signal word
Warning
Hazard statements
371 · H371
Precautionary statements
260 · P260-P264-P270-P308+P311-P405-P501
Hazard Codes
Xn,F,Xi
Risk Statements
36 · 36-68/20/21/22-20/21/22-40-22
Safety Statements
36 · 36-26-36/37-24/25
WGK Germany
3 · 3
RTECS
3450000 · UU3450000
TSCA
TSCA listed
HS Code
29349990 · 29349990
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active

Upstream raw materials

Concentrated hydrochloric acidResin columnAnion exchange resin,strong basic quarternary ammoniumⅠAMBERLITE(R) IRC-50Resin 201BrownIon exchange resin columnSpectrophotometerCation exchange resin,weak acidic acrylic acidCation exchange resin,strong acidic styrene 001×7×7Potassium chlorideYeast extractAmmonia

Downstream products

Cadp-riboseNADPH

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
苏州华赛生物工程技术有限公司0512-89581819; 18915732708 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
苏州顺奕祥生物科技有限公司15973717224
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
张家港市思普生化有限公司512-0512-58992291,58992287 18606280718 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
济南健丰化工有限公司0531-88110457; 18954159893 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海克琴科技有限公司+86-21-67299971;+86-21-67290723 18117322963 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
尚科生物医药(上海)有限公司021-68187180 13681683526 · [email protected]
Advent Bio, Inc.(630) 889-9003 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
湖南复瑞生物医药技术有限责任公司15901640172,19275032510 15901640172 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
陕西帕尼尔生物科技有限公司13720616393;029-84385017-8003 13720616393 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海卫希医药科技有限公司021-56789108 18550363168 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
Additional notes · 1 item

DefinitionChEBI: β-Nicotinamide adenine dinucleotide (NAD) is the oxidized form of β-Nicotinamide Adenine Dinucleotide. It exists as an anion under normal physio-logic conditions. It is functionally related to a deamido-NAD zwitterion. It is a conjugate base of a NAD(+). 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). (Dorland, 27th ed)