Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Angiotensin II (HMDB01035)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:46 -0700
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 | 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 Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
6.418e-06 +/- 2.535e-06 uM Not Specified Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
6.418e-06 +/- 2.535e-06 uM Adult (>18 years old) Female normal Not Available
Urine Detected and Quantified
Article_icon
0.0000012 +/- 0.0000002 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0000574 +/- 0.0000030 uM Adult (>18 years old) Both Hypertension Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.922e-06 +/- 1.741e-06 uM Adult (>18 years old) Not Specified neuromyelitis optica spectrum disorders with anti-Anti-aquaporin-4(AQP4) antibody Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
3.625e-06 +/- 1.473e-06 uM Adult (>18 years old) Not Specified multiple sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
4.907e-06 +/- 2.171e-06 uM Adult (>18 years old) Not Specified inflammatory neuropathies Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.922e-06 +/- 1.741e-06 uM Adult (>18 years old) Female Neuromyelitis optica Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
5.174e-06 +/- 2.238e-06 uM Adult (>18 years old) Both Other neurological diseases Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
3.0000e-06 +/- 1.597e-06 uM Adult (>18 years old) Both multiple sclerosis Not Available
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
    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 Not Available
    Enzymes
    Name: 6-phosphogluconate dehydrogenase, decarboxylating
    Reactions:
    • 6-phospho-D-gluconate + NADP+ = D-ribulose 5-phosphate + CO2 + NADPH [RN:R01528]
    Gene Name: PGD
    Uniprot ID: P52209 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ribose-5-phosphate isomerase
    Reactions:
    • D-ribose 5-phosphate = D-ribulose 5-phosphate [RN:R01056]
    Gene Name: RPIA
    Uniprot ID: P49247 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Angiotensin-converting enzyme
    Reactions:
    • Release of a C-terminal dipeptide, oligopeptide!Xaa-Yaa, when Xaa is not Pro, and Yaa is neither Asp nor Glu. Thus, conversion of angiotensin I to angiotensin II, with increase in vasoconstrictor activity, but no action on angiotensin II COFACTOR Zinc [CPD:C00038] INHIBITOR (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(mercaptomethyl)-1-oxoprolyl]g lycine [CPD:C01313]
    • (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(mercaptomethyl)-1-oxoprolyl]- (S)-alanine [CPD:C01314]
    • (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(acetylthio)methyl-1-oxoprolyl ]glycine benzyl ester [CPD:C01315]
    • (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(acetylthio)methyl-1-oxoprolyl ]-(S)-alanine benzyl ester [CPD:C01316]
    Gene Name: ACE
    Uniprot ID: P12821 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Type-1 angiotensin II receptor
    Reactions:
      Gene Name: AGTR1
      Uniprot ID: P30556 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ribulose-phosphate 3-epimerase
      Reactions:
      • D-ribulose 5-phosphate = D-xylulose 5-phosphate [RN:R01529]
      Gene Name: RPE
      Uniprot ID: Q96AT9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative uncharacterized protein PGD
      Reactions:
        Gene Name: PGD
        Uniprot ID: A9Z1X1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Angiotensin-converting enzyme 2
        Reactions:
        • angiotensin II + H2O = angiotensin-(1--7) + L-phenylalanine
        Gene Name: ACE2
        Uniprot ID: Q9BYF1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Type-2 angiotensin II receptor
        Reactions:
          Gene Name: AGTR2
          Uniprot ID: P50052 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Type-1 angiotensin II receptor-associated protein
          Reactions:
            Gene Name: AGTRAP
            Uniprot ID: Q6RW13 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA