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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:02 UTC
HMDB IDHMDB0001036
Secondary Accession Numbers
  • HMDB01036
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
Data?1582752172
Synonyms
ValueSource
Des-asp-1-angiotensin IIHMDB
Angiotensin II, des-aspMeSH, HMDB
Des asp angiotensin IIMeSH, HMDB
Des aspartyl angiotensin IIMeSH, HMDB
Des-asp angiotensin IIMeSH, HMDB
Des-aspartyl-angiotensin IIMeSH, HMDB
(2S)-2-({[(2S)-1-[(2S)-2-{[(2S,3S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoateGenerator, HMDB
Angiotensin IIIMeSH
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 KeyQMMRCKSBBNJCMR-KMZPNFOHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Isoleucine or derivatives
  • N-acyl-alpha-amino acid
  • Valine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Imidazolyl carboxylic acid derivative
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty amide
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Imidazole
  • Azole
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Guanidine
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboximidamide
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Amine
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity246.48 m³·mol⁻¹ChemAxon
Polarizability98.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+299.57632859911
AllCCS[M-H]-270.68732859911
DeepCCS[M+H]+296.38130932474
DeepCCS[M-H]-294.65730932474
DeepCCS[M-2H]-328.95730932474
DeepCCS[M+Na]+302.7130932474
AllCCS[M+H]+299.632859911
AllCCS[M+H-H2O]+300.132859911
AllCCS[M+NH4]+299.132859911
AllCCS[M+Na]+298.932859911
AllCCS[M-H]-270.732859911
AllCCS[M+Na-2H]-276.232859911
AllCCS[M+HCOO]-282.332859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 10V, Positive-QTOFsplash10-06vi-5961232228-ea4adf55f419bbf3e0a82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 20V, Positive-QTOFsplash10-0200-6921010000-78b0faf8ce8050666bf02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 40V, Positive-QTOFsplash10-0209-9410000000-bbebe48db6281a8863392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 10V, Negative-QTOFsplash10-000i-1000000092-4a7a50dd8f3ff61c013e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 20V, Negative-QTOFsplash10-08fr-7312022291-47ca9d35823f8d1251132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 40V, Negative-QTOFsplash10-08fu-9232011110-c5464e972b484b1210fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 10V, Negative-QTOFsplash10-004i-0000100009-cb682999fd045f9fc4d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 20V, Negative-QTOFsplash10-03kc-5295211253-96684706f7b52c76d77e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 40V, Negative-QTOFsplash10-03kd-6648180390-5726793f99bc63ef56112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 10V, Positive-QTOFsplash10-001i-0223330329-7bdcba8cf45b54090ccb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 20V, Positive-QTOFsplash10-06tr-3922011002-e608edceb9299f7d9e642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angiotensin III 40V, Positive-QTOFsplash10-00dr-9500012201-3a78900784d621a6a3892021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. [PubMed:12609766 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022384
KNApSAcK IDNot Available
Chemspider ID2339529
KEGG Compound IDC15848
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngiotensin
METLIN IDNot Available
PubChem Compound3082042
PDB IDNot Available
ChEBI ID1183270
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Arita M, Wanaka Y: [Angiotensin I, angiotensin II, angiotensin III]. Nihon Rinsho. 1999 Dec;57 Suppl:382-5. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:2197067 ]
  12. Symonds EM: Renin and reproduction. Am J Obstet Gynecol. 1988 Apr;158(4):754-61. [PubMed:3284361 ]
  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 ]
  14. Dimitrov T: [Renin-angiotensin system blockers]. Eksp Med Morfol. 1982;21(2):49-54. [PubMed:6183092 ]
  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 ]
  16. Ganong WF: The brain renin-angiotensin system. Annu Rev Physiol. 1984;46:17-31. [PubMed:6324655 ]
  17. Smith RD, Timmermans PB: Human angiotensin receptor subtypes. Curr Opin Nephrol Hypertens. 1994 Jan;3(1):112-22. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9537002 ]
  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 ]
  24. Chansel D, Ardaillou R: [Active metabolites derived from angiotensin II]. Nephrologie. 1998;19(7):427-32. [PubMed: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. [PubMed:14996614 ]
  26. Arita M: [Angiotensin I, angiotensin II, angiotensin III]. Nihon Rinsho. 2005 Aug;63 Suppl 8:564-7. [PubMed:16149578 ]
  27. Kono T: [Diagnostic tests for endocrine hypertension]. Rinsho Byori. 1984 Jan;Spec No 58:144-55. [PubMed: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. [PubMed: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. [PubMed: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