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CHEBI:145536 - motixafortide

ChEBI IDCHEBI:145536
ChEBI Namemotixafortide
Stars
DefinitionA heterodetic cyclic peptide that has antineoplastic activity. It is a CXC chemokine receptor 4 (CXCR4) antagonist with an IC50 value of 0.8 nM and is currently under clinical investigation for the treatment of hematological malignancies, solid tumors, and stem cell mobilization. It was granted orphan drug designation by the FDA for the treatment of pancreatic cancer in 2019.
Last Modified16 April 2024
SubmitterAdnan
DownloadsMolfile
FormulaC97H144FN33O19S2
Net Charge0
Average Mass2159.563
Monoisotopic Mass2158.07417
SMILES[H][C@@]12CCCN1C(=O)[C@@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc3ccccc3c1)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)c1ccc(F)cc1)CSSC[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(N)=O)NC(=O)[C@H](CCCNC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccc(O)cc1)NC2=O
InChIInChI=1S/C97H144FN33O19S2/c98-60-33-31-58(32-34-60)78(135)119-65(19-8-42-113-93(104)105)79(136)121-68(21-10-44-115-95(108)109)83(140)126-73(51-56-25-30-57-14-1-2-15-59(57)48-56)87(144)130-75-53-152-151-52-74(88(145)118-63(77(101)134)18-7-41-112-92(102)103)129-84(141)69(23-12-46-117-97(111)150)122-81(138)66(20-9-43-114-94(106)107)124-86(143)72(50-55-28-37-62(133)38-29-55)128-90(147)76-24-13-47-131(76)91(148)70(17-4-6-40-100)125-82(139)64(16-3-5-39-99)120-80(137)67(22-11-45-116-96(110)149)123-85(142)71(127-89(75)146)49-54-26-35-61(132)36-27-54/h1-2,14-15,25-38,48,63-76,132-133H,3-13,16-24,39-47,49-53,99-100H2,(H2,101,134)(H,118,145)(H,119,135)(H,120,137)(H,121,136)(H,122,138)(H,123,142)(H,124,143)(H,125,139)(H,126,140)(H,127,146)(H,128,147)(H,129,141)(H,130,144)(H4,102,103,112)(H4,104,105,113)(H4,106,107,114)(H4,108,109,115)(H3,110,116,149)(H3,111,117,150)/t63-,64-,65-,66-,67-,68-,69-,70+,71-,72-,73-,74-,75-,76-/m0/s1
InChIKeyJJVZSYKFCOBILL-KZGZZEQFSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
C-X-C chemokine receptor type 4 antagonist  An antogonist that blocks C-X-C chemokine receptor type 4 (CXCR-4).
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
motixafortide (CHEBI:145536) has role antineoplastic agent (CHEBI:35610)
motixafortide (CHEBI:145536) has role apoptosis inducer (CHEBI:68495)
motixafortide (CHEBI:145536) has role C-X-C chemokine receptor type 4 antagonist (CHEBI:145438)
motixafortide (CHEBI:145536) is a heterodetic cyclic peptide (CHEBI:24533)
Incoming Relation(s)
motixafortide acetate (CHEBI:229224) has part motixafortide (CHEBI:145536)
IUPAC Name 
(3S,6S,9S,12R,17R,20S,23S,26S,29R,34aS)-26,29-bis(4-aminobutyl)-N-[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]-17-{[(2S)-2-{[(2S)-5-carbamimidamido-2-{[(2S)-5-carbamimidamido-2-(4-fluorobenzamido)pentanoyl]amino}pentanoyl]amino}-3-(naphthalen-2-yl)propanoyl]amino}-6-(3-carbamimidamidopropyl)-9,23-bis[3-(carbamoylamino)propyl]-3,20-bis(4-hydroxybenzyl)-1,4,7,10,18,21,24,27,30-nonaoxotriacontahydro-1H,16H-pyrrolo[2,1-p][1,2,5,8,11,14,17,20,23,26,29]dithianonaazacyclodotriacontine-12-carboxamide (non-preferred name)
INNs  Source
motixafortidumWHO MedNet
motixafortideWHO MedNet
motixafortidaWHO MedNet
motixafortideWHO MedNet
Synonyms  Source
BL-8040ChemIDplus
4F-benzoyl-TN14003ChemIDplus
TF 14016ChemIDplus
BKT 140ChemIDplus
BKT140ChEBI
BKT-140ChEBI
Manual XrefsDatabases
DB14939DrugBank
MotixafortideWikipedia
D12281KEGG DRUG
Registry NumbersSources
CAS:664334-36-5ChemIDplus
Citations