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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:02 UTC
HMDB IDHMDB0001038
Secondary Accession Numbers
  • HMDB01038
Metabolite Identification
Common NameAngiotensin IV
DescriptionAngiotensin IV is one of the N-terminal angiotensin degradation products of angiotensin II. Angiotensin IV (AngIV) mediates important physiologic functions in the central nervous system, including blood flow regulation, processes underlying to learning and memory, and presents anticonvulsant activity. The presence of AngIV-specific binding sites has been identified in various mammalian tissues, including blood vessels, heart, kidney, and brain. Besides the presence of AngIV binding sites in the cardiovascular system, the major AngIV synthesizing enzymes aminopeptidase N (APN) and aminopeptidase B (APB) are also expressed in different cell types of this system. AngIV activates several protein kinases, including phosphatidylinositol 3 kinase, PI-dependent kinase-1, extracellular signal-related kinases (ERK), protein kinase B-α/Akt, and p70 ribosomal S6 kinase. AngIV could contribute to vascular damage, increasing the production of monocyte chemoattractant protein-1, the main chemokine involved in monocyte recruitment, and up-regulates the expression of the adhesion molecule intercellular adhesion molecule-1 that is involved in the attachment and transmigration of circulating cells into the damaged tissue. (PMID: 17210474 ).
Structure
Data?1582752172
Synonyms
ValueSource
(3-8)-5-Isoleucine-angiotensin IIHMDB
(Des(asp1,arg2)-ile5)angiotensin IIHMDB
(Ile5)-angiotensin II (3-8)HMDB
(Isoleucine5)-angiotensin II hexapeptideHMDB
1-De-asp-2-de-arg-5-ile-angiotensin IIHMDB, MeSH
3-L-Isoleucine-angiotensin IVHMDB
5-Isoleucine-angiotensin II 3-8-hexapeptideHMDB
Huamn angiotensin (3-8)HMDB
Human angiotensin hexapeptide (3-8)HMDB
Human angiotensin IVHMDB
Ile3-angiotensin IVHMDB
Nle-angivHMDB, MeSH
Val-tyr-ile-his-pro-pheHMDB
Angiotensin II (3-8)MeSH, HMDB
(a)II(3-8)MeSH, HMDB
(2S)-2-({[(2S)-1-[(2S)-2-{[(2S,3S)-2-{[(2S)-2-{[(2S)-2-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 IVMeSH
Chemical FormulaC40H54N8O8
Average Molecular Weight774.9056
Monoisotopic Molecular Weight774.406460744
IUPAC Name(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-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-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(3H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
CAS Registry Number12676-15-2
SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](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/C40H54N8O8/c1-5-24(4)34(47-35(50)29(44-37(52)33(41)23(2)3)18-26-13-15-28(49)16-14-26)38(53)45-30(20-27-21-42-22-43-27)39(54)48-17-9-12-32(48)36(51)46-31(40(55)56)19-25-10-7-6-8-11-25/h6-8,10-11,13-16,21-24,29-34,49H,5,9,12,17-20,41H2,1-4H3,(H,42,43)(H,44,52)(H,45,53)(H,46,51)(H,47,50)(H,55,56)/t24-,29-,30-,31-,32-,33-,34-/m0/s1
InChI KeyQSBGWDDCOJYQGY-KOQODJNWSA-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 or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • Proline or derivatives
  • Valine or derivatives
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • N-acylpyrrolidine
  • Imidazolyl carboxylic acid derivative
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty amide
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP-0.02ALOGPS
logP-0.69ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)8.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area248.94 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity206.05 m³·mol⁻¹ChemAxon
Polarizability81.13 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available31661259
DarkChem[M-H]-PredictedNot Available31661259
AllCCS[M+H]+PredictedNot Available273.58632859911
AllCCS[M-H]-PredictedNot Available241.95232859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9110011100-a3258af2b2d9226eb5b12017-11-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05i0-9333111700-14438c0cf0988f0ffc122017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9421100000-d33bc783ea8124621eb12017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-9110000000-3cb009e3846d24c0ca2a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0111014900-8196ca65b68e830aa1392017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3755249700-66e6b1d97af4f404f9742017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xs-5942121100-d5301aa9e94760ddecc62017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0010000900-025a8f8f62cc328993142021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-3319776200-b6c046ee2046c4304b772021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0j4l-1931012100-16c8654e08576a2f4fcb2021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022385
KNApSAcK IDNot Available
Chemspider ID110363
KEGG Compound IDC15849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngiotensin
METLIN IDNot Available
PubChem Compound123814
PDB IDNot Available
ChEBI ID528953
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Enzymes

General function:
Involved in proteolysis
Specific function:
Release of an N-terminal amino acid, cleaves before cysteine, leucine as well as other amino acids. Degrades peptide hormones such as oxytocin, vasopressin and angiotensin III, and plays a role in maintaining homeostasis during pregnancy. May be involved in the inactivation of neuronal peptides in the brain. Cleaves Met-enkephalin and dynorphin. Binds angiotensin IV and may be the angiotensin IV receptor in the brain
Gene Name:
LNPEP
Uniprot ID:
Q9UIQ6
Molecular weight:
117348.1