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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:00:20 UTC
HMDB IDHMDB0001035
Secondary Accession Numbers
  • HMDB01035
Metabolite Identification
Common NameAngiotensin II
DescriptionAngiotensin II is a hormone that may act on the central nervous system to regulate renal sympathetic nerve activity, renal function, and, therefore, blood pressure. Angiotensin II is produced locally within the kidney and mediates tissue injury through a series of nonhemodynamic effects. angiotensin II is not only involved in the regulation of blood pressure, water and sodium homeostasis, and control of other neurohumoral systems, but also leads to excessive production of reactive oxygen species and to hypertrophy, proliferation, migration, and apoptosis of vascular cells. Angiotensin II is one of the main factors involved in hypertension-induced tissue damage. This peptide regulates the inflammatory process. Angiotensin II activates circulating cells, and participates in their adhesion to the activated endothelium and subsequent transmigration through the synthesis of adhesion molecules, chemokines and cytokines. Among the intracellular signals involved in angiotensin II-induced inflammation, the production of reactive oxygen species and the activation of nuclear factor-kappaB are the best known. Classical, well-defined actions of Angiotensin II in the brain include the regulation of hormone formation and release, the control of the central and peripheral sympathoadrenal systems, and the regulation of water and sodium intake. As a consequence of changes in the hormone, sympathetic and electrolyte systems, feedback mechanisms in turn modulate the activity of the brain Angiotensin II systems. There are two Angiotensin II systems in the brain. The discovery of brain Angiotensin II receptors located in neurons inside the blood brain barrier confirmed the existence of an endogenous brain Angiotensin II system, responding to Angiotensin II generated in and/or transported into the brain. In addition, Angiotensin II receptors in circumventricular organs and in cerebrovascular endothelial cells respond to circulating Angiotensin II of peripheral origin. Thus, the brain responds to both circulating and tissue Angiotensin II, and the two systems are integrated. (PMID: 17147923 , 16672146 , 16601568 , 16481883 , 16075377 ).
Structure
Thumb
Synonyms
ValueSource
5-Isoleucine-angiotensin IIChEBI
5-L-Isoleucineangiotensin IIChEBI
AngiotensinChEBI
Angiotensin II (human)ChEBI
Angiotensin II (mouse)ChEBI
AngiotoninChEBI
Asp-arg-val-tyr-ile-his-pro-pheChEBI
Human angiotensin IIChEBI
HypertensinChEBI
Isoleucine(5)-angiotensin IIChEBI
N-(1-(N-(N-(N-(N-(N(2)-L-alpha-Aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanineChEBI
N-(1-(N-(N-(N-(N-(N(2)-L-a-Aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanineGenerator
N-(1-(N-(N-(N-(N-(N(2)-L-α-aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanineGenerator
1-8-Angiotensin IHMDB
1-L-Aspasaginyl-5-L-valyl angiotensin octapeptideHMDB
Ang IIHMDB
Angiotensin 2HMDB
Ile(5)-angiotensin IIHMDB
II, 5-L-isoleucine angiotensinMeSH
Isoleucyl(5)-angiotensin IIMeSH
Angiotensin II, 5-L-isoleucineMeSH
Valyl(5)-angiotensin IIMeSH
ANG-(1-8)octapeptideMeSH
Isoleucine(5)-angiotensinMeSH
5 L Isoleucine angiotensin IIMeSH
5-L-Isoleucine angiotensin IIMeSH
Angiotensin-(1-8) octapeptideMeSH
Chemical FormulaC50H71N13O12
Average Molecular Weight1046.1786
Monoisotopic Molecular Weight1045.534514801
IUPAC Name(3S)-3-amino-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl]carbamoyl}propanoic acid
Traditional Name(3S)-3-amino-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-(3H-imidazol-4-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl]carbamoyl}propanoic acid
CAS Registry Number11128-99-7
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](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)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/C50H71N13O12/c1-5-28(4)41(47(72)59-36(23-31-25-54-26-56-31)48(73)63-20-10-14-38(63)45(70)60-37(49(74)75)22-29-11-7-6-8-12-29)62-44(69)35(21-30-15-17-32(64)18-16-30)58-46(71)40(27(2)3)61-43(68)34(13-9-19-55-50(52)53)57-42(67)33(51)24-39(65)66/h6-8,11-12,15-18,25-28,33-38,40-41,64H,5,9-10,13-14,19-24,51H2,1-4H3,(H,54,56)(H,57,67)(H,58,71)(H,59,72)(H,60,70)(H,61,68)(H,62,69)(H,65,66)(H,74,75)(H4,52,53,55)/t28-,33-,34-,35-,36-,37-,38-,40-,41-/m0/s1
InChI KeyCZGUSIXMZVURDU-JZXHSEFVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Aspartic acid or derivatives
  • Isoleucine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Valine or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Amphetamine or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine-2-carboxamide
  • Imidazolyl carboxylic acid derivative
  • Pyrrolidine carboxylic acid or derivatives
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty amide
  • Benzenoid
  • N-acyl-amine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Carboximidamide
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Vascular disorders:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

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 Solubility0.016 g/LALOGPS
logP-0.87ALOGPS
logP-5.3ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)10.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area408.84 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity269.81 m³·mol⁻¹ChemAxon
Polarizability107.02 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03mj-9313022101-6ac3b05e269115b1f5adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9724022100-1dce7a6f99b2d561c0b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p6-9111000000-18aeed5d9ab235b9a89bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zi3-9000000005-bb2ec7da92fff6a158acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9110001228-620241ce085107b44de3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9510024340-d26443900117133d12caView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Angiotensin MetabolismPw000563Pw000563 greyscalePw000563 simpleNot Available
Benazepril PathwayPw000223Pw000223 greyscalePw000223 simpleNot Available
Candesartan Action PathwayPw000278Pw000278 greyscalePw000278 simpleNot Available
Captopril PathwayPw000224Pw000224 greyscalePw000224 simpleNot Available
Cilazapril PathwayPw000225Pw000225 greyscalePw000225 simpleNot Available
Displaying entries 1 - 5 of 23 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified6.418e-06 +/- 2.535e-06 uMNot SpecifiedNot SpecifiedNormal details
    Cerebrospinal Fluid (CSF)Detected and Quantified6.418e-06 +/- 2.535e-06 uMAdult (>18 years old)Femalenormal details
    UrineDetected and Quantified0.0000012 +/- 0.0000002 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.0000574 +/- 0.0000030 uMAdult (>18 years old)BothHypertension details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.922e-06 +/- 1.741e-06 uMAdult (>18 years old)Not Specifiedneuromyelitis optica spectrum disorders with anti-Anti-aquaporin-4(AQP4) antibody details
    Cerebrospinal Fluid (CSF)Detected and Quantified3.625e-06 +/- 1.473e-06 uMAdult (>18 years old)Not Specifiedmultiple sclerosis details
    Cerebrospinal Fluid (CSF)Detected and Quantified4.907e-06 +/- 2.171e-06 uMAdult (>18 years old)Not Specifiedinflammatory neuropathies details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.922e-06 +/- 1.741e-06 uMAdult (>18 years old)FemaleNeuromyelitis optica details
    Cerebrospinal Fluid (CSF)Detected and Quantified5.174e-06 +/- 2.238e-06 uMAdult (>18 years old)Both
    Neurological diseases
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified3.0000e-06 +/- 1.597e-06 uMAdult (>18 years old)Bothmultiple sclerosis 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
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022383
    KNApSAcK IDNot Available
    Chemspider ID150504
    KEGG Compound IDC02135
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkAngiotensin II
    METLIN IDNot Available
    PubChem Compound172198
    PDB IDNot Available
    ChEBI ID2719
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Malpas SC, Ramchandra R, Guild SJ, McBryde F, Barrett CJ: Renal sympathetic nerve activity in the development of hypertension. Curr Hypertens Rep. 2006 Jun;8(3):242-8. [PubMed:17147923 ]
    2. Durvasula RV, Shankland SJ: The renin-angiotensin system in glomerular podocytes: mediator of glomerulosclerosis and link to hypertensive nephropathy. Curr Hypertens Rep. 2006 May;8(2):132-8. [PubMed:16672146 ]
    3. Wassmann S, Nickenig G: Pathophysiological regulation of the AT1-receptor and implications for vascular disease. J Hypertens Suppl. 2006 Mar;24(1):S15-21. [PubMed:16601568 ]
    4. Ruiz-Ortega M, Esteban V, Ruperez M, Sanchez-Lopez E, Rodriguez-Vita J, Carvajal G, Egido J: Renal and vascular hypertension-induced inflammation: role of angiotensin II. Curr Opin Nephrol Hypertens. 2006 Mar;15(2):159-66. [PubMed:16481883 ]
    5. Saavedra JM: Brain angiotensin II: new developments, unanswered questions and therapeutic opportunities. Cell Mol Neurobiol. 2005 Jun;25(3-4):485-512. [PubMed:16075377 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
    Gene Name:
    PGD
    Uniprot ID:
    P52209
    Molecular weight:
    53139.56
    General function:
    Involved in ribose-5-phosphate isomerase activity
    Specific function:
    Not Available
    Gene Name:
    RPIA
    Uniprot ID:
    P49247
    Molecular weight:
    33268.72
    General function:
    Involved in metallopeptidase activity
    Specific function:
    Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
    Gene Name:
    ACE
    Uniprot ID:
    P12821
    Molecular weight:
    149713.7
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
    Gene Name:
    AGTR1
    Uniprot ID:
    P30556
    Molecular weight:
    41060.5
    General function:
    Involved in catalytic activity
    Specific function:
    Catalyzes the reversible epimerization of D-ribulose 5-phosphate to D-xylulose 5-phosphate.
    Gene Name:
    RPE
    Uniprot ID:
    Q96AT9
    Molecular weight:
    19537.385
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    PGD
    Uniprot ID:
    A9Z1X1
    Molecular weight:
    32311.5
    General function:
    Involved in metallopeptidase activity
    Specific function:
    Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin-13 with high efficiency. May be an important regulator of heart function. In case of human coronaviruses SARS and HCoV-NL63 infections, serve as functional receptor for the spike glycoprotein of both coronaviruses.
    Gene Name:
    ACE2
    Uniprot ID:
    Q9BYF1
    Molecular weight:
    92462.4
    Reactions
    Angiotensin II + Water → angiotensin-(1-7) + L-Phenylalaninedetails
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for angiotensin II. Cooperates with MTUS1 to inhibit ERK2 activation and cell proliferation
    Gene Name:
    AGTR2
    Uniprot ID:
    P50052
    Molecular weight:
    41183.4
    General function:
    Involved in protein binding
    Specific function:
    Appears to be a negative regulator of type-1 angiotensin II receptor-mediated signaling by regulating receptor internalisation as well as mechanism of receptor desensitization such as phosphorylation. Induces also a decrease in cell proliferation and angiotensin II-stimulated transcriptional activity
    Gene Name:
    AGTRAP
    Uniprot ID:
    Q6RW13
    Molecular weight:
    17419.0