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Showing metabocard for Octreotide (HMDB0014262)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:48 UTC
Update Date2017-12-07 02:44:38 UTC
HMDB IDHMDB0014262
Secondary Accession Numbers
  • HMDB14262
Metabolite Identification
Common NameOctreotide
DescriptionOctreotide is only found in individuals that have used or taken this drug. It is the acetate salt of a cyclic octapeptide. It is a long-acting octapeptide with pharmacologic properties mimicking those of the natural hormone somatostatin.Octreotide binds to somatostatin receptors. These receptors are coupled via pertussis toxin sensitive G proteins which lead to inhibition of adenylyl cyclase. Octreotide binding to these receptors also stimulates phosphotyrosine phosphatase and activation of the Na(+)/H(+) exchanger via pertussis toxin insensitive G proteins.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
OctrotideHMDB
Compound 201 995MeSH
SandostatineMeSH
Sandoz 201 995MeSH
SandostatinMeSH
Sandoz 201995MeSH
Sandoz 201-995MeSH
Compound 201-995MeSH
Compound 201995MeSH
Octreotide acetateMeSH
Octreotide acetate saltMeSH
Chemical FormulaC49H66N10O10S2
Average Molecular Weight1019.239
Monoisotopic Molecular Weight1018.440479762
IUPAC Name(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
Traditional Name(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
CAS Registry Number83150-76-9
SMILES
C[C@@H](O)[C@@H](CO)NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@H](N)CC2=CC=CC=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@H](CC2=CNC3=C2C=CC=C3)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)O)C(=O)N1
InChI Identifier
InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)/t28-,29?,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1
InChI KeyDEQANNDTNATYII-RRCPSWKPSA-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
  • Cyclic alpha peptide
  • Phenylalanine or derivatives
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • Fatty amide
  • Fatty acyl
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Organic disulfide
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Primary aliphatic amine
  • Primary amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP0.42ALOGPS
logP-1.4ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)11.4ChemAxon
pKa (Strongest Basic)10.17ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area332.22 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity269.77 m³·mol⁻¹ChemAxon
Polarizability105.28 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-001i-3321012903-7c8eab8f1beb4afaffb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-5900000175-f303ffbfb6827990c5b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fl0-0913331100-93a936b3ce1f0b40d408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1170000139-4c05920f8d843ed533e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fa5-2010120439-d6441e37ecfed8c37adbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ukc-6913223210-decadc5fa24af7d5ade6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00104 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00104 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482007
KEGG Compound IDC07306
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOctreotide
METLIN IDNot Available
PubChem Compound6400441
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Uhl W, Anghelacopoulos SE, Friess H, Buchler MW: The role of octreotide and somatostatin in acute and chronic pancreatitis. Digestion. 1999;60 Suppl 2:23-31. [PubMed:10207228 ]

Enzymes

Enzyme Details
1. Myeloperoxidase
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Alatas E, Alatas O, Colak O: Octreotide inhibits myeloperoxidase activity in rat uterus. Acta Obstet Gynecol Scand. 2000 Jul;79(7):524-7. [PubMed:10929949 ]
  2. Alatas E, Gunal O, Alatas O, Colak O: Octreotide prevents postoperative adhesion formation by suppressing peritoneal myeloperoxidase activity. Hepatogastroenterology. 2000 Jul-Aug;47(34):1034-6. [PubMed:11020872 ]
Enzyme Details
2. Somatostatin receptor type 2
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for somatostatins-14 and -28. This receptor is coupled via pertussis toxin sensitive G proteins to inhibition of adenylyl cyclase. In addition it stimulates phosphotyrosine phosphatase and PLC via pertussis toxin insensitive as well as sensitive G proteins. In RIN-5F cells, this receptor inhibits calcium entry by suppressing voltage dependent calcium-channels
Gene Name:
SSTR2
Uniprot ID:
P30874
Molecular weight:
41332.4
References
  1. Yim CB, Boerman OC, de Visser M, de Jong M, Dechesne AC, Rijkers DT, Liskamp RM: Versatile conjugation of octreotide to dendrimers by cycloaddition ("click") chemistry to yield high-affinity multivalent cyclic Peptide dendrimers. Bioconjug Chem. 2009 Jul;20(7):1323-31. doi: 10.1021/bc900052n. [PubMed:19537708 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]