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2D Structure
Also known as: Arginine vasopressin, 113-79-1, Argipressine, Pitressin, Beta-hypophamine, 8-arginine-vasopressin
Molecular Formula
C46H65N15O12S2
Molecular Weight
1084.2  g/mol
InChI Key
KBZOIRJILGZLEJ-LGYYRGKSSA-N

The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
2.1.2 InChI
InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
2.1.3 InChI Key
KBZOIRJILGZLEJ-LGYYRGKSSA-N
2.1.4 Canonical SMILES
C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N
2.1.5 Isomeric SMILES
C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Arg Vasopressin

2. Arg-vasopressin

3. Arginine Vasopressin

4. Argipressin Tannate

5. Vasopressin, Arginine

2.2.2 Depositor-Supplied Synonyms

1. Arginine Vasopressin

2. 113-79-1

3. Argipressine

4. Pitressin

5. Beta-hypophamine

6. 8-arginine-vasopressin

7. Argipressin Tannate

8. Vasopressin (arginine Form)

9. Arginine-vasopressin

10. Chebi:34543

11. Vasophysin

12. Arg-vasopressin

13. Chembl373742

14. (arg8)-vasopressin

15. [arg8]-vasopressin

16. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

17. 8-l-arginine Vasopressin

18. Argipresina

19. Argipressina

20. Argipressinum

21. Avp

22. Arg8-vasopressin

23. Argipressin [inn]

24. Argipressina [dcit]

25. Ncgc00166306-01

26. Argipressin [inn:ban]

27. 8-l-arginine-vasopressin

28. Argipresina [inn-spanish]

29. Argipressine [inn-french]

30. Argipressinum [inn-latin]

31. Unii-y4907o6mfd

32. Rindervasopressin

33. [3h]vasopressin

34. Einecs 204-035-4

35. 3-(phenylalanine)-8-arginineoxytocin

36. Arg8-vasopressin;avp

37. Arginine-8-vasopressin

38. Argipressin Or Lypressin

39. [8-arginine]vasopressin

40. [3h]argipressin Tannate

41. Antidiuretic Hormone (adh)

42. Arginine Vasopressin (avp)

43. Argipressin Tannate [usan]

44. Arginine Antidiuretic Hormone

45. Dsstox_cid_28324

46. Dsstox_rid_82752

47. Dsstox_gsid_48349

48. Schembl43139

49. Vasopressin, 8-l-arginine-

50. [cyclo S-s]cyfqncprg-nh2

51. Gtpl2168

52. Y4907o6mfd

53. Dtxsid0048349

54. Schembl17874853

55. Bdbm35667

56. Tox21_113037

57. Bdbm50044777

58. Mfcd00076738

59. Ncgc00166306-02

60. Ncgc00188439-01

61. Cas-113-79-1

62. H-cys-tyr-phe-gln-asn-cys-pro-arg-gly-nh2

63. Oxytocin, 3-(l-phenylalanine)-8-l-arginine-

64. Vasopressin, 8-l-arginine- (7ci,8ci,9ci)

65. Roxybenzyl-6,9,12,15,18-pentaoxo- (6ci)

66. 113a791

67. Q183011

68. Cys-tyr-phe-gln-asn-cys-pro-arg-gly-nh2[disulfide Bridge: 1-6]

69. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

70. 1,2-dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide, 19-amino-13-benzyl-7-(carbamoylmethyl)-4-[2-[[1-[(carbamoylmethyl)carbamoyl]-4-guanidinobutyl]carbamoyl]-1-pyrrolidinylcarbonyl]-16-p-hyd

71. 1-{[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-l-prolyl-l-arginylglycinamide

72. Glycinamide, L-cysteinyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-arginyl-, Cyclic (1>6)-disulfide

2.3 Create Date
2005-06-01
3 Chemical and Physical Properties
Molecular Weight 1084.2 g/mol
Molecular Formula C46H65N15O12S2
XLogP3-4.8
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count16
Rotatable Bond Count19
Exact Mass1083.43785492 g/mol
Monoisotopic Mass1083.43785492 g/mol
Topological Polar Surface Area515 Ų
Heavy Atom Count75
Formal Charge0
Complexity2070
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)


Antidiuretic Agents

Agents that reduce the excretion of URINE, most notably the octapeptide VASOPRESSINS. (See all compounds classified as Antidiuretic Agents.)


Hemostatics

Agents acting to arrest the flow of blood. Absorbable hemostatics arrest bleeding either by the formation of an artificial clot or by providing a mechanical matrix that facilitates clotting when applied directly to the bleeding surface. These agents function more at the capillary level and are not effective at stemming arterial or venous bleeding under any significant intravascular pressure. (See all compounds classified as Hemostatics.)