Human Metabolome Database Version 3.5

Showing metabocard for Somatostatin (HMDB13072)

Record Information
Version 3.5
Creation Date 2009-07-24 18:12:44 -0600
Update Date 2013-07-24 12:10:30 -0600
HMDB ID HMDB13072
Secondary Accession Numbers None
Metabolite Identification
Common Name Somatostatin
Description Somatostatin 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 Link_out). 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 Link_out, 6142531 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. growth hormone-inhibiting hormone (GHIH)
  2. somatotropin release-inhibiting factor (SRIF)
  3. somatotropin release-inhibiting hormone
Chemical Formula C77H106N18O19S2
Average Molecular Weight 1651.905
Monoisotopic Molecular Weight 1650.73230468
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 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)-7,10,13,16,19,22,25,2
CAS Registry Number Not 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 Key KTEPWBJBSMMZIC-LJTSQLRWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class Cyclic 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 Parent Cyclic Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.021 g/L ALOGPS
LogP -1.81 ALOGPS
LogP -7.9 ChemAxon
LogS -4.91 ALOGPS
pKa (strongest acidic) 3.01 ChemAxon
pKa (strongest basic) 10.47 ChemAxon
Hydrogen Acceptor Count 22 ChemAxon
Hydrogen Donor Count 22 ChemAxon
Polar Surface Area 613.23 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 425.02 ChemAxon
Polarizability 170.09 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
8.289e-06 +/- 4.840e-06 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
4.447e-05 +/- 5.0000e-06 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
5.25e-05 +/- 9.9e-06 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.28e-05 +/- 5.4e-06 uM Not Specified Not Specified Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 5.0000e-05 +/- 6.777e-06 uM Children (1-13 year old) Not Specified febrile seizure
Cerebrospinal Fluid (CSF) Detected and Quantified 2.136e-05 +/- 2.602e-06 uM Children (1-13 year old) Not Specified epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 1.204e-05 +/- 3.267e-06 uM Adult (>18 years old) Not Specified post-traumatic stress disorder 
Cerebrospinal Fluid (CSF) Detected and Quantified 6.529e-05 +/- 5.869e-06 uM Adult (>18 years old) Not Specified Parkinsoni an syndrome
Cerebrospinal Fluid (CSF) Detected and Quantified 2.04e-05 +/- 8.1e-06 uM Adult (>18 years old) Not Specified Parkinson disease
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029283
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link somatostatin Link_out
NuGOwiki Link HMDB13072 Link_out
Metagene Link HMDB13072 Link_out
METLIN ID Not Available
PubChem Compound 53481605 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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 Link_out
  2. 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 Link_out
  3. Shen LP, Rutter WJ: Sequence of the human somatostatin I gene. Science. 1984 Apr 13;224(4645):168-71. Pubmed: 6142531 Link_out