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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:44 UTC
HMDB IDHMDB01036
Secondary Accession NumbersNone
Metabolite Identification
Common NameAngiotensin III
DescriptionAngiotensin 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 , 11751722 , 11295571 ).
Structure
Thumb
Synonyms
ValueSource
Des-asp-1-angiotensin IIHMDB
Chemical FormulaC46H66N12O9
Average Molecular Weight931.0912
Monoisotopic Molecular Weight930.50757177
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 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 acid
CAS Registry Number12687-51-3
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 KeyInChIKey=QMMRCKSBBNJCMR-KMZPNFOHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • N-acyl-l-alpha-amino acid
  • Phenylpropylamine
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Imidazolyl carboxylic acid derivative
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Imidazole
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 mg/mLALOGPS
logP-0.79ALOGPS
logP-1.8ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)11.18ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area342.44 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity246.48 m3·mol-1ChemAxon
Polarizability98.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000215 +/- 0.0000022 uMAdult (>18 years old)BothHypertension details
Associated Disorders and Diseases
Disease References
Hypertension
  1. Sim MK, Qui XS: Angiotensins in plasma of hypertensive rats and human. Regul Pept. 2003 Mar 28;111(1-3):179-82. [12609766 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022384
KNApSAcK IDNot Available
Chemspider ID2339529
KEGG Compound IDC15848
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngiotensin III
NuGOwiki LinkHMDB01036
Metagene LinkHMDB01036
METLIN IDNot Available
PubChem Compound3082042
PDB IDNot Available
ChEBI ID1183270
References
Synthesis ReferenceNot 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. [10778144 ]
  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. [11751722 ]
  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. [12428219 ]
  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. [12584663 ]
  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. [15529593 ]
  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. [15748538 ]
  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. [15894523 ]
  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. [16842210 ]
  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. [17094048 ]
  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. [190880 ]
  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. [2197067 ]
  12. Symonds EM: Renin and reproduction. Am J Obstet Gynecol. 1988 Apr;158(4):754-61. [3284361 ]
  13. Levens NR: Control of intestinal absorption by the renin-angiotensin system. Am J Physiol. 1985 Jul;249(1 Pt 1):G3-15. [3893156 ]
  14. Dimitrov T: [Renin-angiotensin system blockers] Eksp Med Morfol. 1982;21(2):49-54. [6183092 ]
  15. Stokes GS: The renin angiotensin system--its physiology and role in disease states. Anaesth Intensive Care. 1983 Nov;11(4):369-76. [6316802 ]
  16. Ganong WF: The brain renin-angiotensin system. Annu Rev Physiol. 1984;46:17-31. [6324655 ]
  17. Smith RD, Timmermans PB: Human angiotensin receptor subtypes. Curr Opin Nephrol Hypertens. 1994 Jan;3(1):112-22. [7850406 ]
  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. [8170622 ]
  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. [8574286 ]
  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. [8923799 ]
  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. [9370053 ]
  22. Dimitrov Y, Muller S, Hannedouche T: [Renal effects of AT1 angiotensin receptor antagonists (AT1ra)] Presse Med. 1997 Dec 20;26(40):1981-6. [9537002 ]
  23. Moeller I, Allen AM, Chai SY, Zhuo J, Mendelsohn FA: Bioactive angiotensin peptides. J Hum Hypertens. 1998 May;12(5):289-93. [9655649 ]
  24. Chansel D, Ardaillou R: [Active metabolites derived from angiotensin II] Nephrologie. 1998;19(7):427-32. [9857379 ]
  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. [14996614 ]
  26. Arita M: [Angiotensin I, angiotensin II, angiotensin III] Nippon Rinsho. 2005 Aug;63 Suppl 8:564-7. [16149578 ]
  27. Kono T: [Diagnostic tests for endocrine hypertension] Rinsho Byori. 1984 Jan;Spec No 58:144-55. [6088844 ]
  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. [17210474 ]
  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. [11295571 ]

Enzymes

General function:
Involved in binding
Specific function:
Aminopeptidases catalyze the hydrolysis of amino acid residues from the N-terminus of peptide or protein substrates. Able to cleave angiotensin III to generate angiotensin IV, a bioactive peptide of the renin-angiotensin pathway. Not able to cleave angiotensin I and angiotensin II. May play a role in the proteolytic processing of bioactive peptides in tissues such as testis and heart
Gene Name:
AOPEP
Uniprot ID:
Q8N6M6
Molecular weight:
93571.6