Human Metabolome Database Version 3.5

Showing metabocard for Angiotensin III (HMDB01036)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-24 11:51:27 -0600
HMDB ID HMDB01036
Secondary Accession Numbers None
Metabolite Identification
Common Name Angiotensin III
Description Angiotensin III (AngIII) is one of the N-terminal angiotensin degradation products of angiotensin II. AngIII shares some of its properties with Ang II, including chemotaxis and production of growth factors and chemokines. AngIII generated within the brain acts within neural circuits of the central nervous system to regulate body fluid balance. The stimulation of vasopressin release by AngIII is thought to be one of the mechanisms by which AngIII controls volume homeostasis under conditions of hypovolemia, by reducing renal water loss and increasing blood pressure. Brain aminopeptidase A, the enzyme forming central AngIII, could constitute a putative central therapeutic target for the treatment of hypertension. (PMID: 17210474 Link_out, 11751722 Link_out, 11295571 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. Des-Asp-1-Angiotensin II
Chemical Formula C46H66N12O9
Average Molecular Weight 931.0912
Monoisotopic Molecular Weight 930.50757177
IUPAC Name (2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
Traditional IUPAC Name (2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(3H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic
CAS Registry Number 12687-51-3
SMILES CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCN=C(N)N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier InChI=1S/C46H66N12O9/c1-5-27(4)38(57-40(61)33(21-29-15-17-31(59)18-16-29)53-42(63)37(26(2)3)56-39(60)32(47)13-9-19-51-46(48)49)43(64)54-34(23-30-24-50-25-52-30)44(65)58-20-10-14-36(58)41(62)55-35(45(66)67)22-28-11-7-6-8-12-28/h6-8,11-12,15-18,24-27,32-38,59H,5,9-10,13-14,19-23,47H2,1-4H3,(H,50,52)(H,53,63)(H,54,64)(H,55,62)(H,56,60)(H,57,61)(H,66,67)(H4,48,49,51)/t27-,32-,33-,34-,35-,36-,37-,38-/m0/s1
InChI Key QMMRCKSBBNJCMR-KMZPNFOHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Alpha Amino Acid Or Derivative
  • Aminoimidazole
  • Amphetamine Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Guanidine
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Phenol
  • Phenol Derivative
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrolidine
  • Secondary Carboxylic Acid Amide
  • Tertiary Carboxylic Acid Amide
Direct Parent Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.014 g/L ALOGPS
LogP -0.79 ALOGPS
LogP -1.8 ChemAxon
LogS -4.82 ALOGPS
pKa (strongest acidic) 3.51 ChemAxon
pKa (strongest basic) 11.18 ChemAxon
Hydrogen Acceptor Count 14 ChemAxon
Hydrogen Donor Count 11 ChemAxon
Polar Surface Area 342.44 A2 ChemAxon
Rotatable Bond Count 25 ChemAxon
Refractivity 246.48 ChemAxon
Polarizability 98.53 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0000215 +/- 0.0000022 uM Adult (>18 years old) Both Hypertension
Associated Disorders and Diseases
Disease References
Hypertension
  • Sim MK, Qui XS: Angiotensins in plasma of hypertensive rats and human. Regul Pept. 2003 Mar 28;111(1-3):179-82. Pubmed: 12609766 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022384
      KNApSAcK ID Not Available
      Chemspider ID 2339529 Link_out
      KEGG Compound ID C15848 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Angiotensin III Link_out
      NuGOwiki Link HMDB01036 Link_out
      Metagene Link HMDB01036 Link_out
      METLIN ID Not Available
      PubChem Compound 3082042 Link_out
      PDB ID Not Available
      ChEBI ID 1183270 Link_out
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Arita M, Wanaka Y: [Angiotensin I, angiotensin II, angiotensin III] Nippon Rinsho. 1999 Dec;57 Suppl:382-5. Pubmed: 10778144 Link_out
      2. Ruiz-Ortega M, Lorenzo O, Ruperez M, Esteban V, Suzuki Y, Mezzano S, Plaza JJ, Egido J: Role of the renin-angiotensin system in vascular diseases: expanding the field. Hypertension. 2001 Dec 1;38(6):1382-7. Pubmed: 11751722 Link_out
      3. Llorens-Cortes C, Mendelsohn FA: Organisation and functional role of the brain angiotensin system. J Renin Angiotensin Aldosterone Syst. 2002 Sep;3 Suppl 1:S39-48. Pubmed: 12428219 Link_out
      4. Vauquelin G, Michotte Y, Smolders I, Sarre S, Ebinger G, Dupont A, Vanderheyden P: Cellular targets for angiotensin II fragments: pharmacological and molecular evidence. J Renin Angiotensin Aldosterone Syst. 2002 Dec;3(4):195-204. Pubmed: 12584663 Link_out
      5. Haulica I, Petrescu G, Slatineanu SM, Bild W, Mihaila CN, Ionita T: New bioactive angiotensins formation pathways and functional involvements. Rom J Intern Med. 2004;42(1):27-40. Pubmed: 15529593 Link_out
      6. Reaux-Le Goazigo A, Iturrioz X, Fassot C, Claperon C, Roques BP, Llorens-Cortes C: Role of angiotensin III in hypertension. Curr Hypertens Rep. 2005 Apr;7(2):128-34. Pubmed: 15748538 Link_out
      7. Nomura S, Ito T, Yamamoto E, Sumigama S, Iwase A, Okada M, Shibata K, Ando H, Ino K, Kikkawa F, Mizutani S: Gene regulation and physiological function of placental leucine aminopeptidase/oxytocinase during pregnancy. Biochim Biophys Acta. 2005 Aug 1;1751(1):19-25. Pubmed: 15894523 Link_out
      8. Martinez-Martos JM, Ramirez-Exposito MJ: Dietary fat and hypertension: a novel approach through the proteolytic regulatory enzymes of the renin-angiotensin-system. Cardiovasc Hematol Agents Med Chem. 2006 Jul;4(3):263-76. Pubmed: 16842210 Link_out
      9. Banegas I, Prieto I, Vives F, Alba F, de Gasparo M, Segarra AB, Hermoso F, Duran R, Ramirez M: Brain aminopeptidases and hypertension. J Renin Angiotensin Aldosterone Syst. 2006 Sep;7(3):129-34. Pubmed: 17094048 Link_out
      10. Skeggs LT, Dorer FE, Kahn JR, Lentz KE, Levine M: The biochemistry of the renin-angiotensin system and its role in hypertension. Am J Med. 1976 May 31;60(6):737-48. Pubmed: 190880 Link_out
      11. Hanley MR, Cheung WT, Hawkins P, Poyner D, Benton HP, Blair L, Jackson TR, Goedert M: The mas oncogene as a neural peptide receptor: expression, regulation and mechanism of action. Ciba Found Symp. 1990;150:23-38; discussion 38-46. Pubmed: 2197067 Link_out
      12. Symonds EM: Renin and reproduction. Am J Obstet Gynecol. 1988 Apr;158(4):754-61. Pubmed: 3284361 Link_out
      13. Levens NR: Control of intestinal absorption by the renin-angiotensin system. Am J Physiol. 1985 Jul;249(1 Pt 1):G3-15. Pubmed: 3893156 Link_out
      14. Dimitrov T: [Renin-angiotensin system blockers] Eksp Med Morfol. 1982;21(2):49-54. Pubmed: 6183092 Link_out
      15. Stokes GS: The renin angiotensin system--its physiology and role in disease states. Anaesth Intensive Care. 1983 Nov;11(4):369-76. Pubmed: 6316802 Link_out
      16. Ganong WF: The brain renin-angiotensin system. Annu Rev Physiol. 1984;46:17-31. Pubmed: 6324655 Link_out
      17. Smith RD, Timmermans PB: Human angiotensin receptor subtypes. Curr Opin Nephrol Hypertens. 1994 Jan;3(1):112-22. Pubmed: 7850406 Link_out
      18. Wright JW, Harding JW: Brain angiotensin receptor subtypes in the control of physiological and behavioral responses. Neurosci Biobehav Rev. 1994 Spring;18(1):21-53. Pubmed: 8170622 Link_out
      19. Wada N, Kubo M, Kijima H, Yamane Y, Nishikawa T, Sasano H, Koike T: A case of deoxycorticosterone-producing adrenal adenoma. Endocr J. 1995 Oct;42(5):637-42. Pubmed: 8574286 Link_out
      20. Mosimann R, Imboden H, Felix D: The neuronal role of angiotensin II in thirst, sodium appetite, cognition and memory. Biol Rev Camb Philos Soc. 1996 Nov;71(4):545-59. Pubmed: 8923799 Link_out
      21. Wright JW, Harding JW: Important role for angiotensin III and IV in the brain renin-angiotensin system. Brain Res Brain Res Rev. 1997 Sep 30;25(1):96-124. Pubmed: 9370053 Link_out
      22. Dimitrov Y, Muller S, Hannedouche T: [Renal effects of AT1 angiotensin receptor antagonists (AT1ra)] Presse Med. 1997 Dec 20;26(40):1981-6. Pubmed: 9537002 Link_out
      23. Moeller I, Allen AM, Chai SY, Zhuo J, Mendelsohn FA: Bioactive angiotensin peptides. J Hum Hypertens. 1998 May;12(5):289-93. Pubmed: 9655649 Link_out
      24. Chansel D, Ardaillou R: [Active metabolites derived from angiotensin II] Nephrologie. 1998;19(7):427-32. Pubmed: 9857379 Link_out
      25. Gard PR: Angiotensin as a target for the treatment of Alzheimer's disease, anxiety and depression. Expert Opin Ther Targets. 2004 Feb;8(1):7-14. Pubmed: 14996614 Link_out
      26. Arita M: [Angiotensin I, angiotensin II, angiotensin III] Nippon Rinsho. 2005 Aug;63 Suppl 8:564-7. Pubmed: 16149578 Link_out
      27. Kono T: [Diagnostic tests for endocrine hypertension] Rinsho Byori. 1984 Jan;Spec No 58:144-55. Pubmed: 6088844 Link_out
      28. Ruiz-Ortega M, Esteban V, Egido J: The regulation of the inflammatory response through nuclear factor-kappab pathway by angiotensin IV extends the role of the renin angiotensin system in cardiovascular diseases. Trends Cardiovasc Med. 2007 Jan;17(1):19-25. Pubmed: 17210474 Link_out
      29. Reaux A, Fournie-Zaluski MC, Llorens-Cortes C: Angiotensin III: a central regulator of vasopressin release and blood pressure. Trends Endocrinol Metab. 2001 May-Jun;12(4):157-62. Pubmed: 11295571 Link_out

      Enzymes
      Name: Aminopeptidase O
      Reactions: Not Available
      Gene Name: AOPEP
      Uniprot ID: Q8N6M6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA