CHEBI:80249 - somatostatin-28

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ChEBI Name somatostatin-28
ChEBI ID CHEBI:80249
Definition A heterodetic cyclic peptide consisting of somatostatin in which the amino terminus has been acylated by the fourteen membered peptide Ser-Ala-Asn-Ser-Asn-Pro-Ala-Met-Ala-Pro-Arg-Glu-Arg-Lys.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C137H207N41O39S3
Net Charge 0
Average Mass 3148.564
Monoisotopic Mass 3146.46370
InChI InChI=1S/C137H207N41O39S3/c1-69(154-113(194)82(37-19-22-47-138)159-115(196)85(40-25-50-149-136(145)146)160-118(199)87(44-45-106(188)189)163-116(197)86(41-26-51-150-137(147)148)164-130(211)101-43-27-52-177(101)133(214)72(4)156-114(195)88(46-54-218-7)158-110(191)71(3)155-129(210)100-42-28-53-178(100)134(215)95(61-104(144)186)171-126(207)96(65-180)172-124(205)93(59-102(142)184)165-111(192)70(2)153-112(193)80(141)64-179)109(190)152-63-105(187)157-98-67-219-220-68-99(135(216)217)174-127(208)97(66-181)173-132(213)108(74(6)183)176-125(206)91(57-77-33-15-10-16-34-77)170-131(212)107(73(5)182)175-119(200)84(39-21-24-49-140)161-122(203)92(58-78-62-151-81-36-18-17-35-79(78)81)168-121(202)90(56-76-31-13-9-14-32-76)166-120(201)89(55-75-29-11-8-12-30-75)167-123(204)94(60-103(143)185)169-117(198)83(162-128(98)209)38-20-23-48-139/h8-18,29-36,62,69-74,80,82-101,107-108,151,179-183H,19-28,37-61,63-68,138-141H2,1-7H3,(H2,142,184)(H2,143,185)(H2,144,186)(H,152,190)(H,153,193)(H,154,194)(H,155,210)(H,156,195)(H,157,187)(H,158,191)(H,159,196)(H,160,199)(H,161,203)(H,162,209)(H,163,197)(H,164,211)(H,165,192)(H,166,201)(H,167,204)(H,168,202)(H,169,198)(H,170,212)(H,171,207)(H,172,205)(H,173,213)(H,174,208)(H,175,200)(H,176,206)(H,188,189)(H,216,217)(H4,145,146,149)(H4,147,148,150)/t69-,70-,71-,72-,73+,74+,80-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,107-,108-/m0/s1
InChIKey GGYTXJNZMFRSLX-DFTNLTQTSA-N
SMILES O=C([C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C)CC(=O)N)CO)CC(=O)N)N1[C@@H](CCC1)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H]3C(N[C@H](C(N[C@H](C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N[C@H](C(=O)O)CSSC3)=O)CO)[C@@H](C)O)CC4=CC=CC=C4)[C@@H](C)O)CCCCN)=O)CC=5C6=C(NC5)C=CC=C6)CC7=CC=CC=C7)CC8=CC=CC=C8)=O)CC(N)=O)=O)CCCCN)=O)C)C)CCSC)C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Rattus norvegicus (NCBI:txid10116) See: PubMed
Pichia pastoris (NCBI:txid4922) See: PubMed
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): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
rat metabolite
Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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-28 (CHEBI:80249) has functional parent somatostatin (CHEBI:64628)
somatostatin-28 (CHEBI:80249) has role fungal metabolite (CHEBI:76946)
somatostatin-28 (CHEBI:80249) has role mouse metabolite (CHEBI:75771)
somatostatin-28 (CHEBI:80249) has role rat metabolite (CHEBI:86264)
somatostatin-28 (CHEBI:80249) is a heterodetic cyclic peptide (CHEBI:24533)
somatostatin-28 (CHEBI:80249) is a peptide hormone (CHEBI:25905)
IUPAC Name
L-seryl-L-alanyl-L-asparaginyl-L-seryl-L-asparaginyl-L-prolyl-L-alanyl-L-methionyl-L-alanyl-L-prolyl-L-arginyl-L-α-glutamyl-L-arginyl-L-lysyl-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-yl)methyl]-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
Synonyms Sources
Ser-Ala-Asn-Ser-Asn-Pro-Ala-Met-Ala-Pro-Arg-Glu-Arg-Lys-Ala-Gly-cyclo-[Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys] ChEBI
Somatostatin-2 KEGG COMPOUND
Somatostatin-28 (sheep) 28 ChemIDplus
SRIF-28 ChEBI
SST-28 ChEBI
Manual Xref Database
C16021 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
10148627 Reaxys Registry Number Reaxys
73032-94-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21564422 PubMed citation Europe PMC
23913690 PubMed citation Europe PMC
24752560 PubMed citation Europe PMC
25009216 PubMed citation Europe PMC
25268135 PubMed citation Europe PMC
26250798 PubMed citation Europe PMC
27715017 PubMed citation Europe PMC
28487631 PubMed citation Europe PMC
28513109 PubMed citation Europe PMC
Last Modified
11 August 2017