CHEBI:64628 - somatostatin

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ChEBI Name somatostatin
ChEBI ID CHEBI:64628
Definition A fourteen-membered heterodetic cyclic peptide comprising the sequence Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys cyclised by a disulfide bridge between the two Cys residues at positions 3 and 14.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6417646, eMolecules:30513112
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Formula C76H104N18O19S2
Net Charge 0
Average Mass 1637.87800
Monoisotopic Mass 1636.71666
InChI InChI=1S/C76H104N18O19S2/c1-41(79)64(100)82-37-61(99)83-58-39-114-115-40-59(76(112)113)92-72(108)57(38-95)91-75(111)63(43(3)97)94-71(107)54(33-46-23-11-6-12-24-46)90-74(110)62(42(2)96)93-66(102)51(28-16-18-30-78)84-69(105)55(34-47-36-81-49-26-14-13-25-48(47)49)88-68(104)53(32-45-21-9-5-10-22-45)86-67(103)52(31-44-19-7-4-8-20-44)87-70(106)56(35-60(80)98)89-65(101)50(85-73(58)109)27-15-17-29-77/h4-14,19-26,36,41-43,50-59,62-63,81,95-97H,15-18,27-35,37-40,77-79H2,1-3H3,(H2,80,98)(H,82,100)(H,83,99)(H,84,105)(H,85,109)(H,86,103)(H,87,106)(H,88,104)(H,89,101)(H,90,110)(H,91,111)(H,92,108)(H,93,102)(H,94,107)(H,112,113)/t41-,42+,43+,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,62-,63-/m0/s1
InChIKey NHXLMOGPVYXJNR-ATOGVRKGSA-N
SMILES C[C@@H](O)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC1=O)[C@@H](C)O)C(O)=O)NC(=O)CNC(=O)[C@H](C)N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via peptide hormone )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing somatostatin (CHEBI:64628) is a heterodetic cyclic peptide (CHEBI:24533)
somatostatin (CHEBI:64628) is a peptide hormone (CHEBI:25905)
Incoming somatostatin-28 (CHEBI:80249) has functional parent somatostatin (CHEBI:64628)
IUPAC Name
L-alanyl-N-[(4R,7S,10S,13S,16S,19S,22S,25S,28S,31S,34S,37R)-19,34-bis(4-aminobutyl)-31-(2-amino-2-oxoethyl)-13,25,28-tribenzyl-4-carboxy-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-37-yl]glycinamide
INNs Sources
somatostatin KEGG DRUG
somatostatina ChemIDplus
somatostatine ChemIDplus
somatostatinum ChemIDplus
Synonyms Sources
Ala-Gly-cyclo-[Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys] ChEBI
L-alanylglycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-L-tryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine cyclic (3-14) disulfide ChemIDplus
Somatostatin-1 KEGG COMPOUND
Somatostatin-14 KEGG COMPOUND
Synthetic growth hormone release-inhibiting hormone ChemIDplus
Manual Xrefs Databases
2997 DrugCentral
C16022 KEGG COMPOUND
D07431 KEGG DRUG
HMDB0013072 HMDB
LSM-5326 LINCS
Somatostatin Wikipedia
View more database links
Registry Numbers Types Sources
10148626 Reaxys Registry Number Reaxys
38916-34-6 CAS Registry Number KEGG DRUG
38916-34-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21922516 PubMed citation Europe PMC
22129035 PubMed citation Europe PMC
22147011 PubMed citation Europe PMC
22251942 PubMed citation Europe PMC
22483686 PubMed citation Europe PMC
22509294 PubMed citation Europe PMC
Last Modified
11 August 2017