| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2021-09-14 15:44:38 UTC |
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| HMDB ID | HMDB0001035 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Angiotensin II |
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| 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 , 16672146 , 16601568 , 16481883 , 16075377 ). |
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| Structure | 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=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 |
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| Synonyms | | Value | Source |
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| 5-Isoleucine-angiotensin II | ChEBI | | 5-L-Isoleucineangiotensin II | ChEBI | | Angiotensin | ChEBI | | Angiotensin II (human) | ChEBI | | Angiotensin II (mouse) | ChEBI | | Angiotonin | ChEBI | | Asp-arg-val-tyr-ile-his-pro-phe | ChEBI | | Human angiotensin II | ChEBI | | Hypertensin | ChEBI | | Isoleucine(5)-angiotensin II | ChEBI | | N-(1-(N-(N-(N-(N-(N(2)-L-alpha-Aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanine | ChEBI | | Delivert | Kegg | | N-(1-(N-(N-(N-(N-(N(2)-L-a-Aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanine | Generator | | N-(1-(N-(N-(N-(N-(N(2)-L-Α-aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanine | Generator | | 1-8-Angiotensin I | HMDB | | 1-L-Aspasaginyl-5-L-valyl angiotensin octapeptide | HMDB | | Ang II | HMDB | | Angiotensin 2 | HMDB | | Ile(5)-angiotensin II | HMDB | | II, 5-L-isoleucine angiotensin | HMDB | | Isoleucyl(5)-angiotensin II | HMDB | | Angiotensin II, 5-L-isoleucine | HMDB | | Valyl(5)-angiotensin II | HMDB | | ANG-(1-8)octapeptide | HMDB | | Isoleucine(5)-angiotensin | HMDB | | 5 L Isoleucine angiotensin II | HMDB | | 5-L-Isoleucine angiotensin II | HMDB | | Angiotensin-(1-8) octapeptide | HMDB |
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| Chemical Formula | C50H71N13O12 |
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| Average Molecular Weight | 1046.1786 |
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| Monoisotopic Molecular Weight | 1045.534514801 |
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| 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 |
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| 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 |
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| CAS Registry Number | 11128-99-7 |
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| 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 |
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| 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 |
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| InChI Key | CZGUSIXMZVURDU-JZXHSEFVSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Oligopeptides |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | |
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| Disposition | |
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| Process | |
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| Role | |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| Spectra |
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| MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 10V, Positive-QTOF | splash10-03mj-9313022101-6ac3b05e269115b1f5ad | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 20V, Positive-QTOF | splash10-03di-9724022100-1dce7a6f99b2d561c0b3 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 40V, Positive-QTOF | splash10-01p6-9111000000-18aeed5d9ab235b9a89b | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 10V, Negative-QTOF | splash10-0zi3-9000000005-bb2ec7da92fff6a158ac | 2016-08-04 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 20V, Negative-QTOF | splash10-0a4i-9110001228-620241ce085107b44de3 | 2016-08-04 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 40V, Negative-QTOF | splash10-0a4l-9510024340-d26443900117133d12ca | 2016-08-04 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 10V, Positive-QTOF | splash10-022d-6194112202-719c98c76d553cec3659 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 20V, Positive-QTOF | splash10-004i-5974214021-eb3b74dcc95ba9b408e9 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 40V, Positive-QTOF | splash10-00bi-3900000320-04aedfa1b8f8c426ec9d | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 10V, Negative-QTOF | splash10-002f-9010000101-5b3797a066dced181aa2 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 20V, Negative-QTOF | splash10-00ai-9214100305-4619422d9477b060e609 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin II 40V, Negative-QTOF | splash10-03di-7252290207-1417dac20cfbdae1d2d1 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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| Biological Properties |
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| Cellular Locations | Not Available |
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| Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Locations | Not Available |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 0.0000086-0.000045 uM | Adolescent (13-18 years old) | Not Specified | Normal | | details | | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000006418 +/- 0.000002535 uM | Not Specified | Not Specified | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000006418 +/- 0.000002535 uM | Adult (>18 years old) | Female | normal | | details | | Urine | Detected and Quantified | 0.0000012 +/- 0.0000002 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected and Quantified | 0.00169 uM | Adolescent (13-18 years old) | Female | Renal tubular acidosis, proximal, with ocular abnormalities and mental retardation | | details | | Blood | Detected and Quantified | 0.0000574 +/- 0.0000030 uM | Adult (>18 years old) | Both | Hypertension | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000001922 +/- 0.000001741 uM | Adult (>18 years old) | Not Specified | neuromyelitis optica spectrum disorders with anti-Anti-aquaporin-4(AQP4) antibody | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000003625 +/- 0.000001473 uM | Adult (>18 years old) | Not Specified | multiple sclerosis | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000004907 +/- 0.000002171 uM | Adult (>18 years old) | Not Specified | inflammatory neuropathies | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000001922 +/- 0.000001741 uM | Adult (>18 years old) | Female | Neuromyelitis optica | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000005174 +/- 0.000002238 uM | Adult (>18 years old) | Both | Neurological diseases | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0000030000 +/- 0.000001597 uM | Adult (>18 years old) | Both | multiple sclerosis | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Hypertension |
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- Sim MK, Qui XS: Angiotensins in plasma of hypertensive rats and human. Regul Pept. 2003 Mar 28;111(1-3):179-82. [PubMed:12609766 ]
| | Renal tubular acidosis, proximal, with ocular abnormalities and mental retardation |
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- Igarashi T, Ishii T, Watanabe K, Hayakawa H, Horio K, Sone Y, Ohga K: Persistent isolated proximal renal tubular acidosis--a systemic disease with a distinct clinical entity. Pediatr Nephrol. 1994 Feb;8(1):70-1. [PubMed:8142230 ]
| | Multiple sclerosis |
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- Matsushita T, Isobe N, Kawajiri M, Mogi M, Tsukuda K, Horiuchi M, Ohyagi Y, Kira J: CSF angiotensin II and angiotensin-converting enzyme levels in anti-aquaporin-4 autoimmunity. J Neurol Sci. 2010 Aug 15;295(1-2):41-5. doi: 10.1016/j.jns.2010.05.014. Epub 2010 Jun 11. [PubMed:20541774 ]
- Kawajiri M, Mogi M, Osoegawa M, Matsuoka T, Tsukuda K, Kohara K, Horiuchi M, Miki T, Kira JI: Reduction of angiotensin II in the cerebrospinal fluid of patients with multiple sclerosis. Mult Scler. 2008 May;14(4):557-60. doi: 10.1177/1352458507085760. [PubMed:18562510 ]
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| Associated OMIM IDs | - 145500 (Hypertension)
- 604278 (Renal tubular acidosis, proximal, with ocular abnormalities and mental retardation)
- 126200 (Multiple sclerosis)
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| External Links |
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| DrugBank ID | DB11842 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB022383 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 150504 |
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| KEGG Compound ID | C02135 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Angiotensin |
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| METLIN ID | Not Available |
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| PubChem Compound | 172198 |
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| PDB ID | Not Available |
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| ChEBI ID | 2719 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| MarkerDB ID | MDB00000295 |
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| Good Scents ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- Saavedra JM: Brain angiotensin II: new developments, unanswered questions and therapeutic opportunities. Cell Mol Neurobiol. 2005 Jun;25(3-4):485-512. [PubMed:16075377 ]
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