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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.)

Drugs in Development