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Angiotensin (1-7)

Angiotensin (1-7)

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Also known as: 51833-78-4, Angiotensin 1-7, Asp-arg-val-tyr-ile-his-pro, Txa127, Angiotensin i (1-7), Angiotensin-(1-7)

Molecular Formula

C₄₁H₆₂N₁₂O₁₁

Molecular Weight

899.0 g/mol

InChI Key

PVHLMTREZMEJCG-GDTLVBQBSA-N

Therapeutic Angiotensin-(1-7) is a synthetic heptapeptide identical to endogenous angiotensin-(1-7) with vasodilator and antiproliferative activities. Therapeutic angiotensin 1-7 may inhibit cyclooxygenase 2 (COX-2) and the production of proinflammatory prostaglandins and may activate the angiotensin-(1-7) receptor Mas, resulting in diminished tumor cell proliferation. Activation of the angiotensin-(1-7) receptor Mas, a G-protein coupled, seven transmembrane protein, may down-regulate the phosphorylation and activation of Erk1 and Erk2 in the Erk1/Erk2 MAPK signaling pathway. In the renin-angiotensin system, the vasodilating activity of angiotensin- (1-7), hydrolysed from angiotensin II by the type I transmembrane metallopeptidase and carboxypeptidase angiotensin converting enzyme 2 (ACE2) in vivo, counteracts the vasoconstricting activity of angiotensin II.

1 2D Structure

Angiotensin (1-7)

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carboxylic acid

2.1.2 InChI

InChI=1S/C41H62N12O11/c1-5-22(4)33(38(61)50-29(17-24-19-45-20-47-24)39(62)53-15-7-9-30(53)40(63)64)52-36(59)28(16-23-10-12-25(54)13-11-23)49-37(60)32(21(2)3)51-35(58)27(8-6-14-46-41(43)44)48-34(57)26(42)18-31(55)56/h10-13,19-22,26-30,32-33,54H,5-9,14-18,42H2,1-4H3,(H,45,47)(H,48,57)(H,49,60)(H,50,61)(H,51,58)(H,52,59)(H,55,56)(H,63,64)(H4,43,44,46)/t22-,26-,27-,28-,29-,30-,32-,33-/m0/s1

2.1.3 InChI Key

PVHLMTREZMEJCG-GDTLVBQBSA-N

2.1.4 Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CN=CN1)C(=O)N2CCCC2C(=O)O)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C(C(C)C)NC(=O)C(CCCN=C(N)N)NC(=O)C(CC(=O)O)N

2.1.5 Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N2CCC[C@H]2C(=O)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(=O)O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ang I (1-7)

2. Angiotensin 1-7

3. Angiotensin I (1-7)

4. Angiotensin Ii (1-7)

5. Angiotensin Ii (1-7) Heptapeptide

6. Angiotensin Ii-(1-7)

7. Angiotensin-(1-7)

8. Angiotensin-i (1-7)

9. Txa-127

10. Txa127

2.2.2 Depositor-Supplied Synonyms

1. 51833-78-4

2. Angiotensin 1-7

3. Asp-arg-val-tyr-ile-his-pro

4. Txa127

5. Angiotensin I (1-7)

6. Angiotensin-(1-7)

7. Angiotensin Ii (1-7) Heptapeptide

8. Angiotensin Ii (1-7)

9. 8-des-phe-angiotensin Ii

10. Ang-(1-7)

11. Txa-127

12. 39386-80-6

13. Angiotensin I/ii (1-7)

14. Chebi:55438

15. Ile(5)-angiotensin Ii (1-7)

16. L-alpha-aspartyl-l-arginyl-l-valyl-l-tyrosyl-l-isoleucyl-l-histidyl-l-proline

17. L-aspartyl-l-arginyl-l-valyl-l-tyrosyl-l-isoleucyl-l-histidyl-l-proline

18. (2s)-1-[(2s)-2-[[(2s,3s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-carboxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]pyrrolidine-2-carboxylic Acid

19. Unii-ij3fuk8mof

20. Angiotensin, Canine, Rat

21. Human Angiotensin-(1-7)

22. 1-7-human Angiotensin Ii

23. Angiotensin Ii, Des-phe(8)-

24. Txa 127

25. Ang-1-7 Acetate

26. Angiotensin(1-7)

27. Mfcd00153513

28. Sh-heptapeptide-13

29. Angiotensini(1-7)

30. Bf-angiotensin 1-7

31. Angiotensin Ii, Des-phenylalanine(8)-

32. Ij3fuk8mof

33. Angiotensin, Canine, Ra

34. Angiotensin I/ii(1-7)

35. Ang 1-7

36. Angiotensin Fragment 1-7

37. 5-ile-angiotensin-(1-7)

38. Angiotensin Peptide (1-7)

39. Gtpl582

40. Ang(1-7)

41. Human Angiotensin Ii (1-7)

42. Angiotensin Ii, 5-l-isoleucine-8-de-l-phenylalanine-

43. Gtpl5578

44. [ile5]angiotensin I (1-7)

45. Angiotensin 1-7 Acetate

46. Chembl3545347

47. Schembl15926158

48. Bdbm85556

49. [125i]ang-(1-7)

50. Txa127; Ang-(1-7)

51. Zinc96077632

52. Akos024456667

53. Cs-3413

54. Db11720

55. Angiotensin Ii, 8-de-l-phenylalanine-

56. Ncgc00167219-01

57. As-76407

58. Hy-12403

59. [125i]angiotensin-(1-7) (human, Mouse, Rat)

60. 833a784

61. A901408

62. Angiotensin I/ii Fragment 1-7 Trifluoroacetate Salt

63. Q27074464

64. Aspartyl-argininyl-valinyl-tyrosinyl-isoleucinyl-histidinyl-proline;angiotensin 1-7

65. (2s)-1-[(2s)-2-[[(2s,3s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-4-hydroxy-4-oxobutanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(3h-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic Acid

66. (s)-1-((6s,9s,12s,15s,18s)-18-((1h-imidazol-4-yl)methyl)-1-amino-6-((s)-2-amino-3-carboxypropanamido)-15-sec-butyl-12-(4-hydroxybenzyl)-1-imino-9-isopropyl-7,10,13,16-tetraoxo-2,8,11,14,17-pentaazanonadecane)pyrrolidine-2-carboxylic Acid

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₆₂N₁₂O₁₁
Molecular Weight	899.0 g/mol
XLogP3	-3
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	25
Exact Mass	898.46610084 g/mol
Monoisotopic Mass	898.46610084 g/mol
Topological Polar Surface Area	380 Å²
Heavy Atom Count	64
Formal Charge	0
Complexity	1660
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

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Vasodilator Agents

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