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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:48 UTC
Update Date2021-09-14 15:18:55 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
Data?1582753164
Synonyms
ValueSource
OctrotideHMDB
Compound 201 995HMDB
SandostatineHMDB
Sandoz 201 995HMDB
SandostatinHMDB
Sandoz 201995HMDB
Sandoz 201-995HMDB
Compound 201-995HMDB
Compound 201995HMDB
Octreotide acetateHMDB
Octreotide acetate saltHMDB
(4R,7S,10S,13R,16S,19R)-19-{[(2R)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-6,9,12,15,18-pentahydroxy-7-(1-hydroxyethyl)-13-[(1H-indol-3-yl)methyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carboximidateGenerator
OctreotideMeSH
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
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.
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

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP10(0.42) g/LALOGPS
logP10(-1.4) g/LChemAxon
logS10(-4.9) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 10V, Positive-QTOFsplash10-001i-3321012903-7c8eab8f1beb4afaffb52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 20V, Positive-QTOFsplash10-0ue9-5900000175-f303ffbfb6827990c5b82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 40V, Positive-QTOFsplash10-0fl0-0913331100-93a936b3ce1f0b40d4082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 10V, Negative-QTOFsplash10-014i-1170000139-4c05920f8d843ed533e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 20V, Negative-QTOFsplash10-0fa5-2010120439-d6441e37ecfed8c37adb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 40V, Negative-QTOFsplash10-0ukc-6913223210-decadc5fa24af7d5ade62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 10V, Negative-QTOFsplash10-014i-9000000008-5ccc89453cdae21c20812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 20V, Negative-QTOFsplash10-06dj-2000000009-63367ff1a2d404b26b932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 40V, Negative-QTOFsplash10-006x-7900000072-b3946d99fea68e0bdcee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 10V, Positive-QTOFsplash10-014i-9200000001-43dd0d1cb54b9e4cc2842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 20V, Positive-QTOFsplash10-0ul3-8400000079-d17587b780e7668727f22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octreotide 40V, Positive-QTOFsplash10-0006-9700000000-589b2999c30497bce6dc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00104 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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

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 ]
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 ]