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Chemistry

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Also known as: Lysine vasopressin, Lysipressin, Syntopressin, 50-57-7, Postacton, Diapid

Molecular Formula

C₄₆H₆₅N₁₃O₁₂S₂

Molecular Weight

1056.2 g/mol

InChI Key

BJFIDCADFRDPIO-DZCXQCEKSA-N

The porcine antidiuretic hormone (VASOPRESSINS). It is a cyclic nonapeptide that differs from ARG-VASOPRESSIN by one amino acid, containing a LYSINE at residue 8 instead of an ARGININE. Lys-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.

1 2D Structure

Lypressin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-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]pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C46H65N13O12S2/c47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34/h1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1

2.1.3 InChI Key

BJFIDCADFRDPIO-DZCXQCEKSA-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(CCCCN)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](CCCCN)C(=O)NCC(=O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 8 Lysine Vasopressin

2. 8-lysine Vasopressin

3. Diapid

4. Lys Vasopressin

5. Lys-vasopressin

6. Lysine Vasopressin

7. Lysyl Vasopressin

8. Postacton

9. Vasopressin, 8-lysine

10. Vasopressin, Lysine

11. Vasopressin, Lysyl

2.2.2 Depositor-Supplied Synonyms

1. Lysine Vasopressin

2. Lysipressin

3. Syntopressin

4. 50-57-7

5. Postacton

6. Diapid

7. Lysine Pitressin

8. 8-l-lysinevasopressin

9. L-lysine Vasopressin

10. Vasopressin-8-lysine

11. Vasopressin Pig

12. Vasopressin, 8-l-lysine-

13. (8-lysine)vasopressin

14. Vasopressin, 8-l-lysine

15. Vasopressin (lysine Form)

16. [lys8]-vasopressin

17. 8-l-lysine Vasopressin

18. 50-57-7 (free Base)

19. [8-lysine]vasopressin

20. Lysine-vasopressin

21. Dsstox_cid_28501

22. Dsstox_rid_82773

23. Dsstox_gsid_48575

24. L-cysteinyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-lysylglycinamide Cyclic (1->6)-disulfide

25. Lipressina

26. Lypressine

27. Lypressinum

28. Lysopressin

29. Lipresina

30. Lysylvasopressin

31. (lys8)-vasopressin

32. Cas-50-57-7

33. (s)-n-((s)-6-amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan-2-yl)-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-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide

34. L-8

35. Lipressina [dcit]

36. Lipresina [inn-spanish]

37. Lypressine [inn-french]

38. Lypressinum [inn-latin]

39. Unii-7czf3l922y

40. 3-(phenylalanine)-8-lysine Oxytocin

41. L-lysinamide,

42. Lysine-adh

43. Lypressin [usan:usp:inn:ban]

44. Ncgc00181743-01

45. Ncgc00181743-02

46. Lvp

47. Einecs 200-050-5

48. Brn 4648365

49. [lys8]avp

50. Schembl33287

51. 7czf3l922y

52. Gtpl2172

53. Chembl1200690

54. Dtxsid8048575

55. Chebi:94802

56. Cys-tyr-phe-gln-asn-cys-pro-lys-gly-nh2, Cyclic 1-6 Disulfide

57. Hy-p0004

58. Tox21_112902

59. Tox21_113427

60. [lys8]-vasopressinlysine Vasopressin

61. Mfcd00076754

62. Ccg-270620

63. Cs-5838

64. Db14642

65. (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-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]pyrrolidine-2-carboxamide

66. Oxytocin, 3-(l-phenylalanine)-8-l-lysine-

67. Vasopressin, 8-l-lysine- (7ci,8ci,9ci)

68. C75370

69. L]carbonyl]-l-prolyl-n-(2-amino-2-oxoethyl)-

70. 076l754

71. Brd-k93331255-001-01-2

72. Q27082434

73. 1,2-dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide

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

75. (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-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]pyrrolidine-2-carboxamide

76. (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-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-pentazacycloeicos-4-yl]-oxomethyl]-2-pyrrolidinecarboxamide

77. 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-pentaazacycloeicos-4-y

78. 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-p Rolyl-l-lysylglycinamide

79. 19-amino-4-[2-[[5-amino-1-[(carbamoylmethyl)carbamoyl]pentyl]carbamoyl]-1-pyrrolidinylcarbonyl]-13-benzyl-7-(carbamoylmethyl)-16-p-hydroxybenzyl-6,9,12,15,18-pentaoxo- (6ci)

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

81. L 8

82. L-cysteinyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-lysylglycinamide Cyclic (1-6)-disulfide

2.3 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₄₆H₆₅N₁₃O₁₂S₂
Molecular Weight	1056.2 g/mol
XLogP3	-3.9
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	19
Exact Mass	1055.43170691 g/mol
Monoisotopic Mass	1055.43170691 g/mol
Topological Polar Surface Area	476 Å²
Heavy Atom Count	73
Formal Charge	0
Complexity	1960
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

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.)

Vasoconstrictor Agents

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

4.2 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H01 - Pituitary and hypothalamic hormones and analogues

H01B - Posterior pituitary lobe hormones

H01BA - Vasopressin and analogues

H01BA03 - Lypressin

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