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Prestwick3_000741
Also known as: Nicotinamide adenine dinucleotide, Nad+, Enzopride, Diphosphopyridine nucleotide, 53-84-9, Adenine-nicotinamide dinucleotide
Molecular Formula
C21H28N7O14P2+
Molecular Weight
664.4  g/mol
InChI Key
BAWFJGJZGIEFAR-NNYOXOHSSA-O

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). (Dorland, 27th ed)
1 2D Structure

Prestwick3_000741

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
2.1.2 InChI
InChI=1S/C21H27N7O14P2/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/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
2.1.3 InChI Key
BAWFJGJZGIEFAR-NNYOXOHSSA-O
2.1.4 Canonical SMILES
C1=CC(=C[N+](=C1)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)C(=O)N
2.1.5 Isomeric SMILES
C1=CC(=C[N+](=C1)[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)C(=O)N
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Adenine Dinucleotide, Dihydronicotinamide

2. Coenzyme I

3. Dihydronicotinamide Adenine Dinucleotide

4. Dinucleotide, Dihydronicotinamide Adenine

5. Dinucleotide, Nicotinamide-adenine

6. Diphosphopyridine Nucleotide

7. Dpn

8. Nad

9. Nadh

10. Nadide

11. Nicotinamide Adenine Dinucleotide

12. Nicotinamide-adenine Dinucleotide

13. Nucleotide, Diphosphopyridine

2.2.2 Depositor-Supplied Synonyms

1. Nicotinamide Adenine Dinucleotide

2. Nad+

3. Enzopride

4. Diphosphopyridine Nucleotide

5. 53-84-9

6. Adenine-nicotinamide Dinucleotide

7. Nad

8. Nadidum [inn-latin]

9. Nadida [inn-spanish]

10. Nad(+)

11. Chebi:15846

12. [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2r,3s,4r,5r)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl Hydrogen Phosphate

13. 151411-04-0

14. Nicotinamide-adenine Dinucleotide

15. Brn 3584133

16. Sr-05000001677

17. Nadide [usan:ban:inn:jan]

18. Nad Cation

19. [[(2r,3s,4r,5r)-5-[(3r)-3-aminocarbonyl-3,4-dihydro-2h-pyridin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanidyl-phosphoryl] [(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl Phosphate

20. 121053-11-0

21. Naj

22. Txe

23. Spectrum_000973

24. Nicotinamide Adenine Dinucleotide (nad+)

25. [[(2~{r},3~{s},4~{r},5~{r})-5-(3-aminocarbonylpyridin-1-ium-1-yl)-4-[[5-[4-cyano-2-[(~{e})-hydroxyiminomethyl]phenoxy]-1-oxidanyl-3~{h}-2,1$l^{4}-benzoxaborol-1-yl]oxy]-3-oxidanyl-oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2~{r},3~{s},4~{r},5~{r})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl Hydrogen Phosphate

26. 9jm

27. Adenosine 5'-(trihydrogen Diphosphate), P'-5'-ester With 3-(aminocarbonyl)-1-beta-d-ribofuranosylpyridinium, Inner Salt

28. Prestwick3_000741

29. Pyridinium, 3-carbamoyl-1-beta-d-ribofuranosyl-, Hydroxide, 5'-ester With Adenosine 5'-5'-(trihydrogen Pyrophosphate), Inner Salt

30. Spectrum2_001056

31. Spectrum3_000511

32. Spectrum4_000065

33. Spectrum5_001291

34. Bmse000053

35. Nadide (jan/usan/inn)

36. Bspbio_000722

37. Bspbio_002061

38. Kbiogr_000589

39. Kbioss_001453

40. Divk1c_000189

41. Spbio_001012

42. Bpbio1_000796

43. Chembl3039307

44. Schembl14478781

45. Kbio1_000189

46. Kbio2_001453

47. Kbio2_004021

48. Kbio2_006589

49. Kbio3_001561

50. Ninds_000189

51. Zinc8214766

52. Idi1_000189

53. 65085-09-8

54. C00003

55. D00002

56. 036d253

57. Sr-05000001677-1

58. Sr-05000001677-3

59. Brd-a11132253-001-01-7

60. Q26987253

61. 1-[5-o-[(5'-adenylyloxy)phosphonyl]-beta-d-ribofuranosyl]-3-(aminocarbonyl)pyridinium

62. Coconut Oil, Polymer With Benzoic Acid, Glycerol, Pentaerythritol And Phthalic Anhydride

63. 865-05-4

64. Adenosine 5'-{3-[1-(3-carbamoylpyridinio)-1,4-anhydro-d-ribitol-5-yl] Dihydrogen Diphosphate}

2.3 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 664.4 g/mol
Molecular Formula C21H28N7O14P2+
XLogP3-5.9
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count18
Rotatable Bond Count11
Exact Mass664.11694759 g/mol
Monoisotopic Mass664.11694759 g/mol
Topological Polar Surface Area318 Ų
Heavy Atom Count44
Formal Charge1
Complexity1130
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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