SD-91   Click here for help

GtoPdb Ligand ID: 11599

Compound class: Synthetic organic
Comment: SD-91 is a selective PROTAC (proteolysis targeting chimaera) degrader of signal transducer and activator of transcription 3 (STAT3) [2]. It induces significant and long-lasting tumour regression in vivo. It is one of the chemical structures that are claimed as STAT3 degraders in patent WO2020198435A1 from The Regents Of The University Of Michigan [1]. SD-91 contains an inhibitor molecule that targets the STAT3 SH2 domain that is linked to a cereblon binding moiety that interacts with the cereblon/cullin 4A E3 ligase to promote proteosomal degradation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 21
Hydrogen bond donors 8
Rotatable bonds 23
Topological polar surface area 337.69
Molecular weight 1135.42
XLogP 3.03
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES NC(=O)CC[C@@H](C(=O)NC(c1ccccc1)c1ccccc1)NC(=O)[C@@H]1CC[C@H]2N1C(=O)[C@H](CN(CC2)C(=O)CCCCCC#Cc1cccc2c1CN(C2=O)C1CCC(=O)NC1=O)NC(=O)c1cc2c([nH]1)ccc(c2)C(=O)P(=O)(O)O
Isomeric SMILES NC(=O)CC[C@@H](C(=O)NC(c1ccccc1)c1ccccc1)NC(=O)[C@@H]1CC[C@H]2N1C(=O)[C@H](CN(CC2)C(=O)CCCCCC#Cc1cccc2c1CN(C2=O)C1CCC(=O)NC1=O)NC(=O)c1cc2c([nH]1)ccc(c2)C(=O)P(=O)(O)O
InChI InChI=1S/C59H62N9O13P/c60-49(69)27-24-44(53(72)65-52(36-14-7-4-8-15-36)37-16-9-5-10-17-37)62-56(75)48-25-22-40-29-30-66(34-46(58(77)68(40)48)63-54(73)45-32-39-31-38(21-23-43(39)61-45)59(78)82(79,80)81)51(71)20-11-3-1-2-6-13-35-18-12-19-41-42(35)33-67(57(41)76)47-26-28-50(70)64-55(47)74/h4-5,7-10,12,14-19,21,23,31-32,40,44,46-48,52,61H,1-3,11,20,22,24-30,33-34H2,(H2,60,69)(H,62,75)(H,63,73)(H,65,72)(H,64,70,74)(H2,79,80,81)/t40-,44+,46+,47?,48+/m1/s1
InChI Key OHDMEJTVYXXZNQ-OPKPGBGESA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
[2-[[(5S,8S,10aR)-8-[[(2S)-5-amino-1-(benzhydrylamino)-1,5-dioxopentan-2-yl]carbamoyl]-3-[8-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-4-yl]oct-7-ynoyl]-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocin-5-yl]carbamoyl]-1H-indole-5-carbonyl]phosphonic acid
Database Links Click here for help
GtoPdb PubChem SID 442878633
PubChem CID 155145010
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