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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:47 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
Thumb
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
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
Val-tyr-ile-his-pro-pheHMDB
Angiotensin II (3-8)MeSH
(a)II(3-8)MeSH
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
DescriptionThis compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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 Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9110011100-a3258af2b2d9226eb5b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05i0-9333111700-14438c0cf0988f0ffc12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9421100000-d33bc783ea8124621eb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-9110000000-3cb009e3846d24c0ca2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0111014900-8196ca65b68e830aa139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3755249700-66e6b1d97af4f404f974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xs-5942121100-d5301aa9e94760ddecc6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022385
KNApSAcK IDNot Available
Chemspider ID110363
KEGG Compound IDC15849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123814
PDB IDNot Available
ChEBI ID528953
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