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Record Information
Version3.6
Creation Date2009-07-25 00:12:44 UTC
Update Date2014-06-12 22:14:33 UTC
HMDB IDHMDB13072
Secondary Accession NumbersNone
Metabolite Identification
Common NameSomatostatin
DescriptionSomatostatin is a peptide hormone that regulates the endocrine system and affects neurotransmission and cell proliferation via interaction with G protein-coupled somatostatin receptors and inhibition of the release of numerous secondary hormones. Somatostatin has two active forms produced by alternative cleavage of a single preproprotein: one of 14 amino acids, the other of 28 amino acids. In all vertebrates, there exists six different somatostatin genes that have been named SS1, SS2, SS3, SS4, SS5, and SS6 (PMID: 20472043 ). The six different genes along with the five different somatostatin receptors allows somatostatin to possess a large range of functions. Humans have only one somatostatin gene, SST (PMID: 6126875 , 6142531 ).
Structure
Thumb
Synonyms
  1. growth hormone-inhibiting hormone (GHIH)
  2. somatotropin release-inhibiting factor (SRIF)
  3. somatotropin release-inhibiting hormone
Chemical FormulaC77H106N18O19S2
Average Molecular Weight1651.905
Monoisotopic Molecular Weight1650.73230468
IUPAC Name(5S,8R,14R,17R,20R,23R,26R,29R,32R,35R)-20,35-bis(4-aminobutyl)-38-{2-[(2R)-2-aminopropanamido]acetamido}-14,26,29-tribenzyl-32-(carbamoylmethyl)-11-(1-hydroxyethyl)-17-[(1S)-1-hydroxyethyl]-8-(hydroxymethyl)-23-(1H-indol-3-ylmethyl)-7,10,13,16,19,22,25,28,31,34,37-undecaoxo-1,2-dithia-6,9,12,15,18,21,24,27,30,33,36-undecaazacyclononatriacontane-5-carboxylic acid
Traditional Name(5S,8R,14R,17R,20R,23R,26R,29R,32R,35R)-20,35-bis(4-aminobutyl)-38-{2-[(2R)-2-aminopropanamido]acetamido}-14,26,29-tribenzyl-32-(carbamoylmethyl)-11-(1-hydroxyethyl)-17-[(1S)-1-hydroxyethyl]-8-(hydroxymethyl)-23-(1H-indol-3-ylmethyl)-7,10,13,16,19,22,25,2
CAS Registry NumberNot Available
SMILES
C[C@H](O)[C@H]1NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@@H](CCCCN)NC(=O)C(CSSCC[C@H](NC(=O)[C@@H](CO)NC(=O)C(NC(=O)[C@@H](CC2=CC=CC=C2)NC1=O)C(C)O)C(O)=O)NC(=O)CNC(=O)[C@@H](C)N
InChI Identifier
InChI=1S/C77H106N18O19S2/c1-42(80)65(101)83-39-62(100)84-60-41-116-115-32-29-53(77(113)114)87-73(109)59(40-96)93-76(112)64(44(3)98)95-72(108)56(35-47-23-11-6-12-24-47)92-75(111)63(43(2)97)94-67(103)52(28-16-18-31-79)85-70(106)57(36-48-38-82-50-26-14-13-25-49(48)50)90-69(105)55(34-46-21-9-5-10-22-46)88-68(104)54(33-45-19-7-4-8-20-45)89-71(107)58(37-61(81)99)91-66(102)51(86-74(60)110)27-15-17-30-78/h4-14,19-26,38,42-44,51-60,63-64,82,96-98H,15-18,27-37,39-41,78-80H2,1-3H3,(H2,81,99)(H,83,101)(H,84,100)(H,85,106)(H,86,110)(H,87,109)(H,88,104)(H,89,107)(H,90,105)(H,91,102)(H,92,111)(H,93,112)(H,94,103)(H,95,108)(H,113,114)/t42-,43+,44?,51-,52-,53+,54-,55-,56-,57-,58-,59-,60?,63-,64?/m1/s1
InChI KeyKTEPWBJBSMMZIC-LJTSQLRWSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassPeptides
Sub ClassCyclic Peptides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Carboxamide Group
  • Carboxylic Acid Salt
  • Indole
  • Lactam
  • N Acyl Alpha Amino Acid
  • Organic Disulfide
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
  • Primary Carboxylic Acid Amide
  • Pyrrole
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentCyclic Peptides
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021ALOGPS
logP-1.8ALOGPS
logP-7.9ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)10.47ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count22ChemAxon
Polar Surface Area613.23 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity425.02 m3·mol-1ChemAxon
Polarizability170.09 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified8.289e-06 +/- 4.840e-06 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4.447e-05 +/- 5.0000e-06 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.25e-05 +/- 9.9e-06 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.28e-05 +/- 5.4e-06 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified5.0000e-05 +/- 6.777e-06 uMChildren (1-13 years old)Not SpecifiedFebrile seizure details
Cerebrospinal Fluid (CSF)Detected and Quantified2.136e-05 +/- 2.602e-06 uMChildren (1-13 years old)Not Specifiedepilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified1.204e-05 +/- 3.267e-06 uMAdult (>18 years old)Not Specifiedpost-traumatic stress disorder  details
Cerebrospinal Fluid (CSF)Detected and Quantified6.529e-05 +/- 5.869e-06 uMAdult (>18 years old)Not SpecifiedParkinsonian syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified2.04e-05 +/- 8.1e-06 uMAdult (>18 years old)Not SpecifiedParkinson's Disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029283
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linksomatostatin
NuGOwiki LinkHMDB13072
Metagene LinkHMDB13072
METLIN IDNot Available
PubChem Compound53481605
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shen LP, Pictet RL, Rutter WJ: Human somatostatin I: sequence of the cDNA. Proc Natl Acad Sci U S A. 1982 Aug;79(15):4575-9. Pubmed: 6126875
  2. Shen LP, Rutter WJ: Sequence of the human somatostatin I gene. Science. 1984 Apr 13;224(4645):168-71. Pubmed: 6142531
  3. Liu Y, Lu D, Zhang Y, Li S, Liu X, Lin H: The evolution of somatostatin in vertebrates. Gene. 2010 Sep 1;463(1-2):21-8. doi: 10.1016/j.gene.2010.04.016. Epub 2010 May 21. Pubmed: 20472043