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Showing metabocard for Octreotide (HMDB14262)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version3.6
Creation Date2012-09-06 15:16:48 UTC
Update Date2016-02-11 01:28:02 UTC
HMDB IDHMDB14262
Secondary Accession NumbersNone
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
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 KeyInChIKey=DEQANNDTNATYII-RRCPSWKPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • Fatty acyl
  • Benzenoid
  • Substituted pyrrole
  • Fatty amide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organic disulfide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anabolic Agents
  • Antineoplastic Agents, Hormonal
  • Gastrointestinal Agents
  • Hormone Replacement Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.22e-02 g/LNot Available
LogP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity269.77 m3·mol-1ChemAxon
Polarizability105.28 Å3ChemAxon
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00104
  • Not Applicable
 details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00104
  • Not Applicable
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00104
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482007
KEGG Compound IDC07306
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOctreotide
NuGOwiki LinkHMDB14262
Metagene LinkHMDB14262
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. [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. [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. [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. [19537708 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]