CHEBI:76649 - astressin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name astressin
ChEBI ID CHEBI:76649
Definition A 30-membered homodetic cyclic peptide comprising the sequence D-Phe-His-Leu-Leu-Arg-Glu-Val-Leu-Glu-Nle-Ala-Arg-Ala-Glu-Gln-Leu-Ala-Gln-Glu-Ala-His-Lys-Asn-Arg-Lys-Leu-Nle-Glu-Ile-Ile-NH2 cyclised by an amide bridge, formed by condensation of the side-chain carboxy group of the Glu residue at position 19 and the side-chain amino group of the Lys residue at position 22.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C161H269N49O42
Net Charge 0
Average Mass 3563.16170
Monoisotopic Mass 3561.04197
InChI InChI=1S/C161H269N49O42/c1-23-27-41-96(189-145(239)107(52-59-123(217)218)199-152(246)114(71-84(13)14)207-157(251)126(85(15)16)208-147(241)108(53-60-124(219)220)197-140(234)102(47-38-66-179-161(172)173)193-151(245)112(69-82(9)10)204-153(247)113(70-83(11)12)205-155(249)116(74-94-77-175-79-181-94)201-134(228)95(163)72-92-39-30-29-31-40-92)135(229)182-88(19)130(224)186-100(45-36-64-177-159(168)169)136(230)183-89(20)131(225)188-106(51-58-122(215)216)144(238)195-104(49-56-119(165)212)146(240)202-110(67-80(5)6)149(243)185-90(21)132(226)187-103(48-55-118(164)211)143(237)196-105-50-57-121(214)176-63-35-33-44-99(192-154(248)115(73-93-76-174-78-180-93)200-133(227)91(22)184-137(105)231)142(236)206-117(75-120(166)213)156(250)194-101(46-37-65-178-160(170)171)139(233)190-98(43-32-34-62-162)141(235)203-111(68-81(7)8)150(244)191-97(42-28-24-2)138(232)198-109(54-61-125(221)222)148(242)210-128(87(18)26-4)158(252)209-127(129(167)223)86(17)25-3/h29-31,39-40,76-91,95-117,126-128H,23-28,32-38,41-75,162-163H2,1-22H3,(H2,164,211)(H2,165,212)(H2,166,213)(H2,167,223)(H,174,180)(H,175,181)(H,176,214)(H,182,229)(H,183,230)(H,184,231)(H,185,243)(H,186,224)(H,187,226)(H,188,225)(H,189,239)(H,190,233)(H,191,244)(H,192,248)(H,193,245)(H,194,250)(H,195,238)(H,196,237)(H,197,234)(H,198,232)(H,199,246)(H,200,227)(H,201,228)(H,202,240)(H,203,235)(H,204,247)(H,205,249)(H,206,236)(H,207,251)(H,208,241)(H,209,252)(H,210,242)(H,215,216)(H,217,218)(H,219,220)(H,221,222)(H4,168,169,177)(H4,170,171,178)(H4,172,173,179)/t86-,87-,88-,89-,90-,91-,95+,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,126-,127-,128-/m0/s1
InChIKey HPYIIXJJVYSMCV-MGDXKYBTSA-N
SMILES CCCC[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](N)Cc1ccccc1)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H]1CCC(=O)NCCCC[C@H](NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@H](C)NC1=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(N)=O
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): corticotropin-releasing factor receptor antagonist
A hormone antagonist that blocks corticotropin-releasing factor receptors
Application(s): corticotropin-releasing factor receptor antagonist
A hormone antagonist that blocks corticotropin-releasing factor receptors
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing astressin (CHEBI:76649) has role corticotropin-releasing factor receptor antagonist (CHEBI:76977)
astressin (CHEBI:76649) has role neuroprotective agent (CHEBI:63726)
astressin (CHEBI:76649) is a homodetic cyclic peptide (CHEBI:24613)
astressin (CHEBI:76649) is a polypeptide (CHEBI:15841)
Synonyms Sources
[D-Phe12, Nle21,38, Glu30, Lys33]-corticotropin releasing factor fragment 12-41 ChEBI
[D-Phe12, Nle21,38, Glu30, Lys33]-CRF (12-41) ChEBI
AST SUBMITTER
D-Phe-His-Leu-Leu-Arg-Glu-Val-Leu-Glu-Nle-Ala-Arg-Ala-Glu-Gln-Leu-Ala-Gln-cyclo-(Glu-Ala-His-Lys)-Asn-Arg-Lys-Leu-Nle-Glu-Ile-Ile-NH2 ChEBI
D-phenylalanyl-L-histidyl-L-leucyl-L-leucyl-L-arginyl-L-α-glutamyl-L-valyl-L-leucyl-L-α-glutamyl-L-norleucyl-L-alanyl-L-arginyl-L-alanyl-L-α-glutamyl-L-glutaminyl-L-leucyl-L-alanyl-L-glutaminyl-cyclo-(L-α-glutamyl-L-alanyl-L-histidyl-L-lysyl)-L-asparaginyl-L-arginyl-L-lysyl-L-leucyl-L-norleucyl-L-α-glutamyl-L-isoleucyl-L-isoleucinamide ChEBI
fHLLREVLE-Nle-ARAEQLAQ-cyclo-(EAHK)NRKL-Nle-EII-NH2 ChEBI
Manual Xref Database
US2002035083 Patent
View more database links
Registry Numbers Types Sources
14669775 Reaxys Registry Number Reaxys
170809-51-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
16 November 2015