Human Metabolome Database Version 3.5

Showing metabocard for Angiotensin II (HMDB01035)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-24 11:51:27 -0600
HMDB ID HMDB01035
Secondary Accession Numbers None
Metabolite Identification
Common Name Angiotensin II
Description Angiotensin 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 Link_out, 16672146 Link_out, 16601568 Link_out, 16481883 Link_out, 16075377 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-8-Angiotensin I
  2. 1-L-Aspasaginyl-5-L-valyl angiotensin octapeptide
  3. Ang II
  4. Angiotensin 2
  5. Angiotensin II (human)
  6. Angiotensin II (mouse)
  7. Angiotonin
  8. Asp-arg-val-TYR-ile-his-pro-phe
  9. Human angiotensin II
  10. Hypertensin
  11. Ile(5)-angiotensin II
Chemical Formula C50H71N13O12
Average Molecular Weight 1046.1786
Monoisotopic Molecular Weight 1045.534514801
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 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-(3H-imidazol-4-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]c
CAS Registry Number 11128-99-7
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 Key CZGUSIXMZVURDU-JZXHSEFVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Angiotensin [KO:K09821](KEGG)
  • Aromatic Heteropolycyclic Compounds
  • amino acid zwitterion(ChEBI)
Substituents
  • 1,3 Aminoalcohol
  • Alpha Amino Acid Or Derivative
  • Aminoimidazole
  • Amphetamine Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Guanidine
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Phenol
  • Phenol Derivative
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrolidine
  • Secondary Carboxylic Acid Amide
  • Tertiary Carboxylic Acid Amide
Direct Parent Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.016 g/L ALOGPS
LogP -0.87 ALOGPS
LogP -5.3 ChemAxon
LogS -4.83 ALOGPS
pKa (strongest acidic) 3.15 ChemAxon
pKa (strongest basic) 10.83 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 13 ChemAxon
Polar Surface Area 408.84 A2 ChemAxon
Rotatable Bond Count 29 ChemAxon
Refractivity 269.81 ChemAxon
Polarizability 107.02 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Cerebrospinal Fluid (CSF) Detected and Quantified
6.418e-06 +/- 2.535e-06 uM Not Specified Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
6.418e-06 +/- 2.535e-06 uM Adult (>18 years old) Female normal
Urine Detected and Quantified
0.0000012 +/- 0.0000002 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0000574 +/- 0.0000030 uM Adult (>18 years old) Both Hypertension
Cerebrospinal Fluid (CSF) Detected and Quantified 1.922e-06 +/- 1.741e-06 uM Adult (>18 years old) Not Specified neuromyelitis optica spectrum disorders with anti-Anti-aquaporin-4(AQP4) antibody
Cerebrospinal Fluid (CSF) Detected and Quantified 3.625e-06 +/- 1.473e-06 uM Adult (>18 years old) Not Specified multiple sclerosis
Cerebrospinal Fluid (CSF) Detected and Quantified 4.907e-06 +/- 2.171e-06 uM Adult (>18 years old) Not Specified inflammatory neuropathies
Cerebrospinal Fluid (CSF) Detected and Quantified 1.922e-06 +/- 1.741e-06 uM Adult (>18 years old) Female Neuromyelitis optica
Cerebrospinal Fluid (CSF) Detected and Quantified 5.174e-06 +/- 2.238e-06 uM Adult (>18 years old) Both Other neurological diseases
Cerebrospinal Fluid (CSF) Detected and Quantified 3.0000e-06 +/- 1.597e-06 uM Adult (>18 years old) Both multiple sclerosis
Associated Disorders and Diseases
Disease References
Hypertension
  • Sim MK, Qui XS: Angiotensins in plasma of hypertensive rats and human. Regul Pept. 2003 Mar 28;111(1-3):179-82. Pubmed: 12609766 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022383
      KNApSAcK ID Not Available
      Chemspider ID 150504 Link_out
      KEGG Compound ID C02135 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Angiotensin II Link_out
      NuGOwiki Link HMDB01035 Link_out
      Metagene Link HMDB01035 Link_out
      METLIN ID Not Available
      PubChem Compound 172198 Link_out
      PDB ID Not Available
      ChEBI ID 2719 Link_out
      References
      Synthesis Reference Not 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: 6-phosphogluconate dehydrogenase, decarboxylating
      Reactions: Not Available
      Gene Name: PGD
      Uniprot ID: P52209 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ribose-5-phosphate isomerase
      Reactions: Not Available
      Gene Name: RPIA
      Uniprot ID: P49247 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Angiotensin-converting enzyme
      Reactions: Not Available
      Gene Name: ACE
      Uniprot ID: P12821 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Type-1 angiotensin II receptor
      Reactions: Not Available
      Gene Name: AGTR1
      Uniprot ID: P30556 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ribulose-phosphate 3-epimerase
      Reactions: Not Available
      Gene Name: RPE
      Uniprot ID: Q96AT9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative uncharacterized protein PGD
      Reactions: Not Available
      Gene Name: PGD
      Uniprot ID: A9Z1X1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Angiotensin-converting enzyme 2
      Reactions:
      Angiotensin II + Water unknown angiotensin-(1-7) + L-Phenylalanine details
      Gene Name: ACE2
      Uniprot ID: Q9BYF1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Type-2 angiotensin II receptor
      Reactions: Not Available
      Gene Name: AGTR2
      Uniprot ID: P50052 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Type-1 angiotensin II receptor-associated protein
      Reactions: Not Available
      Gene Name: AGTRAP
      Uniprot ID: Q6RW13 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA