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(S)-3-[(S)-2-((S)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-phosphonooxy-phenyl)-propionylamino]-4-methyl-pentanoylamino}-5-guanidino-pentanoylamino)-3-mercapto-propionylamino]-4-((S)-1-carbamoyl-2-hydroxy-ethylamino)-butyric acid

ID: ALA348612

PubChem CID: 44372105

Max Phase: Preclinical

Molecular Formula: C33H55N10O13PS

Molecular Weight: 862.90

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](Cc1ccc(OP(=O)(O)O)cc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@H](CS)C(=O)N[C@H](CN[C@@H](CO)C(N)=O)CC(=O)O

Standard InChI:  InChI=1S/C33H55N10O13PS/c1-17(2)11-23(42-31(51)24(39-18(3)45)12-19-6-8-21(9-7-19)56-57(53,54)55)30(50)41-22(5-4-10-37-33(35)36)29(49)43-26(16-58)32(52)40-20(13-27(46)47)14-38-25(15-44)28(34)48/h6-9,17,20,22-26,38,44,58H,4-5,10-16H2,1-3H3,(H2,34,48)(H,39,45)(H,40,52)(H,41,50)(H,42,51)(H,43,49)(H,46,47)(H4,35,36,37)(H2,53,54,55)/t20-,22-,23-,24-,25-,26+/m0/s1

Standard InChI Key:  KIPIAEWATPHWBT-WQUQOGLJSA-N

Molfile:  

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M  END

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: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

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MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

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Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 862.90Molecular Weight (Monoisotopic): 862.3408AlogP: -3.92#Rotatable Bonds: 27
Polar Surface Area: 389.31Molecular Species: ZWITTERIONHBA: 13HBD: 14
#RO5 Violations: 3HBA (Lipinski): 23HBD (Lipinski): 16#RO5 Violations (Lipinski): 3
CX Acidic pKa: 1.79CX Basic pKa: 10.75CX LogP: -8.57CX LogD: -9.26
Aromatic Rings: 1Heavy Atoms: 58QED Weighted: 0.01Np Likeness Score: 0.47

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]

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