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4-{(S)-2-Acetylamino-2-[(S)-1-((R)-2-{(S)-3-carbamoyl-1-[(1S,2R)-1-((S)-1-carbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-propylcarbamoyl]-propylcarbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-ethyl}-benzoic acid

ID: ALA405322

PubChem CID: 44372049

Max Phase: Preclinical

Molecular Formula: C37H56N8O11

Molecular Weight: 788.90

Molecule Type: Protein

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](Cc1ccc(C(=O)O)cc1)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(N)=O)C(C)C)[C@@H](C)O

Standard InChI:  InChI=1S/C37H56N8O11/c1-18(2)16-26(42-33(51)25(40-21(6)47)17-22-9-11-23(12-10-22)37(55)56)36(54)45-15-7-8-27(45)34(52)41-24(13-14-28(38)48)32(50)44-30(20(5)46)35(53)43-29(19(3)4)31(39)49/h9-12,18-20,24-27,29-30,46H,7-8,13-17H2,1-6H3,(H2,38,48)(H2,39,49)(H,40,47)(H,41,52)(H,42,51)(H,43,53)(H,44,50)(H,55,56)/t20-,24+,25+,26+,27-,29+,30+/m1/s1

Standard InChI Key:  RNPPUAIVVNTPFD-PUABCZFRSA-N

Molfile:  

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M  END

Alternative Forms

Associated Targets(Human)

STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: ProteinTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 788.90Molecular Weight (Monoisotopic): 788.4069AlogP: -1.80#Rotatable Bonds: 21
Polar Surface Area: 309.52Molecular Species: ACIDHBA: 10HBD: 9
#RO5 Violations: 2HBA (Lipinski): 19HBD (Lipinski): 11#RO5 Violations (Lipinski): 3
CX Acidic pKa: 4.07CX Basic pKa: CX LogP: -2.31CX LogD: -5.43
Aromatic Rings: 1Heavy Atoms: 56QED Weighted: 0.07Np Likeness Score: -0.07

References

1. Ren Z, Cabell LA, Schaefer TS, McMurray JS..  (2003)  Identification of a high-affinity phosphopeptide inhibitor of Stat3.,  13  (4): [PMID:12639546] [10.1016/s0960-894x(02)01050-8]
2. Mandal, Pijus K PK and 9 more authors.  2009-04-23  Conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription. 3: Evaluation and molecular modeling.  [PMID:19334714]
3. Mandal, Pijus K; Ren, Zhiyong; Chen, Xiaomin; Xiong, Chiyi and McMurray, John S.  2009-10-08  Structure-affinity relationships of glutamine mimics incorporated into phosphopeptides targeted to the SH2 domain of signal transducer and activator of transcription 3.  [PMID:19728728]
4. Ioannidis, Stephanos S and 20 more authors.  2011-01-13  Discovery of 5-chloro-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (AZD1480) as a novel inhibitor of the Jak/Stat pathway.  [PMID:21138246]
5. Mandal, Pijus K and 10 more authors.  2011-05-26  Potent and selective phosphopeptide mimetic prodrugs targeted to the Src homology 2 (SH2) domain of signal transducer and activator of transcription 3.  [PMID:21486047]
6. Ren, Xiaomei X and 8 more authors.  2010-12-09  Identification of Niclosamide as a New Small-Molecule Inhibitor of the STAT3 Signaling Pathway.  [PMID:24900231]
7. Haftchenary, Sina S and 15 more authors.  2013-11-14  Potent Targeting of the STAT3 Protein in Brain Cancer Stem Cells: A Promising Route for Treating Glioblastoma.  [PMID:24900612]
8. LaPorte, Matthew G and 11 more authors.  2014-11-01  2-Guanidinoquinazolines as new inhibitors of the STAT3 pathway.  [PMID:25288188]
9. Miklossy, Gabriella G and 15 more authors.  2015-10-08  Hirsutinolide Series Inhibit Stat3 Activity, Alter GCN1, MAP1B, Hsp105, G6PD, Vimentin, TrxR1, and Importin α-2 Expression, and Induce Antitumor Effects against Human Glioma.  [PMID:26331426]
10. Löcken, Hauke H, Clamor, Cinzia C and Müller, Klaus K.  2018-07-27  Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells.  [PMID:30003778]
11. Huang, Wei W and 8 more authors.  2018-09-05  Small-molecule compounds targeting the STAT3 DNA-binding domain suppress survival of cisplatin-resistant human ovarian cancer cells by inducing apoptosis.  [PMID:30145375]
12. Chen, Shao-Ru SR and 7 more authors.  2018-10-01  Andrographolide derivative as STAT3 inhibitor that protects acute liver damage in mice.  [PMID:30228000]
13. Li, Chungen C and 8 more authors.  2019-01-15  A novel series of napabucasin derivatives as orally active inhibitors of signal transducer and activator of transcription 3 (STAT3).  [PMID:30472602]
14. Zhou, Haibin and 18 more authors.  2019-12-26  Structure-Based Discovery of SD-36 as a Potent, Selective, and Efficacious PROTAC Degrader of STAT3 Protein.  [PMID:31747516]
15. Kaoud, Tamer S and 7 more authors.  2020-01-15  NO-releasing STAT3 inhibitors suppress BRAF-mutant melanoma growth.  [PMID:31784187]
16. Cerulli, Robert A and 6 more authors.  2020-06-15  Cytosolic delivery of peptidic STAT3 SH2 domain inhibitors.  [PMID:32503696]
17. Brotherton-Pleiss, Christine and 13 more authors.  2021-01-14  Discovery of Novel Azetidine Amides as Potent Small-Molecule STAT3 Inhibitors.  [PMID:33352047]

Source