Angiotensin II (CHEM021875)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:34 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021875
Identification
Common NameAngiotensin II
ClassSmall Molecule
DescriptionAngiotensin II is under investigation for the treatment of Sepsis, Septic Shock, Diabetes Mellitus, and Acute Renal Failure. Angiotensin II has been investigated for the treatment, basic science, and diagnostic of Hypertension, Renin Angiotensin System, and Idiopathic Membranous Nephropathy. As of December 21, 2017 the FDA approved La Jolla Pharmaceutical's Giapreza (angiotensin II) Injection for Intravenouse Infusion for the indication of acting as a vasoconstrictor to increase blood pressure in adults with septic or other distributive shock. The novelty of the medication lies in the fact that it is the first and only use of synthetic Angiotensin II to help maintain body blood pressure. Shock is the inability to maintain blood flow to vital tissues and the potential resultant organ failure and death within hours, no matter young or o ld. As distributive shock is the most common type of shock in the inpatient setting and affects up to one third of patients in the intensive care unit, the FDA determined that there is a need for treatment options for critically ill hypotensive patients who do not adequately respond to currently available therapies.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
DelivertKegg
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 angiotensinHMDB
Isoleucyl(5)-angiotensin IIHMDB
Angiotensin II, 5-L-isoleucineHMDB
Valyl(5)-angiotensin IIHMDB
ANG-(1-8)octapeptideHMDB
Isoleucine(5)-angiotensinHMDB
5 L Isoleucine angiotensin IIHMDB
5-L-Isoleucine angiotensin IIHMDB
Angiotensin-(1-8) octapeptideHMDB
Chemical FormulaC50H71N13O12
Average Molecular Mass1046.179 g/mol
Monoisotopic Mass1045.535 g/mol
CAS Registry Number11128-99-7
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
SMILESCC[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 IdentifierInChI=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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03mj-9313022101-6ac3b05e269115b1f5adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9724022100-1dce7a6f99b2d561c0b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p6-9111000000-18aeed5d9ab235b9a89bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zi3-9000000005-bb2ec7da92fff6a158acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9110001228-620241ce085107b44de3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9510024340-d26443900117133d12caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022d-6194112202-719c98c76d553cec3659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5974214021-eb3b74dcc95ba9b408e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bi-3900000320-04aedfa1b8f8c426ec9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-9010000101-5b3797a066dced181aa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ai-9214100305-4619422d9477b060e609Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-7252290207-1417dac20cfbdae1d2d1Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11842
HMDB IDHMDB0001035
FooDB IDFDB022383
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAngiotensin
Chemspider ID150504
ChEBI ID2719
PubChem Compound ID172198
Kegg Compound IDC02135
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.
5. Saavedra JM: Brain angiotensin II: new developments, unanswered questions and therapeutic opportunities. Cell Mol Neurobiol. 2005 Jun;25(3-4):485-512.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16672146