(5S,8S,14S)-14-(2-amino-2-oxoethyl)-5-(2-carboxyethyl)-1-(9H-fluoren-9-yl)-8-(4-hydroxybenzyl)-11,11-dimethyl-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid

ID: ALA2296610

PubChem CID: 76331266

Max Phase: Preclinical

Molecular Formula: C37H41N5O11

Molecular Weight: 731.76

Molecule Type: Protein

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC(C)(NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCC(=O)O)NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)N[C@@H](CC(N)=O)C(=O)O

Standard InChI: InChI=1S/C37H41N5O11/c1-37(2,35(51)40-29(34(49)50)18-30(38)44)42-33(48)28(17-20-11-13-21(43)14-12-20)39-32(47)27(15-16-31(45)46)41-36(52)53-19-26-24-9-5-3-7-22(24)23-8-4-6-10-25(23)26/h3-14,26-29,43H,15-19H2,1-2H3,(H2,38,44)(H,39,47)(H,40,51)(H,41,52)(H,42,48)(H,45,46)(H,49,50)/t27-,28-,29-/m0/s1

Standard InChI Key: XLHAWQAGMMFFQO-AWCRTANDSA-N

Molfile:

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M  END

Associated Targets(Human)

GRB2 Tchem Growth factor receptor-bound protein 2 (663 Activities)

Discover Target: GRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Protein	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 731.76	Molecular Weight (Monoisotopic): 731.2803	AlogP: 1.53	#Rotatable Bonds: 17
Polar Surface Area: 263.55	Molecular Species: ACID	HBA: 9	HBD: 8
#RO5 Violations: 2	HBA (Lipinski): 16	HBD (Lipinski): 9	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.49	CX Basic pKa: ┄	CX LogP: 1.42	CX LogD: -5.10
Aromatic Rings: 3	Heavy Atoms: 53	QED Weighted: 0.10	Np Likeness Score: -0.03

References

1. Hsiao Y, Lee C, Lin Y, Tsai S, Jeng KG, Chao W, Lung FT. (2013) Design, synthesis, and evaluation of fluorescent cell-penetrating peptidic antagonists of Grb2-SH2 for targeting MCF-7 breast cancer cells, 22 (11): [10.1007/s00044-013-0538-z]
2. Yao, Z J ZJ and 6 more authors. 1999-01-14 Potent inhibition of Grb2 SH2 domain binding by non-phosphate-containing ligands. [PMID:9888830]
3. Ettmayer, P P and 10 more authors. 1999-03-25 Structural and conformational requirements for high-affinity binding to the SH2 domain of Grb2(1). [PMID:10090780]
4. Furet, P P and 5 more authors. 1999-07-01 Structure-based design, synthesis, and X-ray crystallography of a high-affinity antagonist of the Grb2-SH2 domain containing an asparagine mimetic. [PMID:10395476]
5. Gao, Y Y and 8 more authors. 2000-03-09 Inhibition of Grb2 SH2 domain binding by non-phosphate-containing ligands. 2. 4-(2-Malonyl)phenylalanine as a potent phosphotyrosyl mimetic. [PMID:10715157]
6. Lee, Kyeong K, Zhang, Manchao M, Liu, Hongpeng H, Yang, Dajun D and Burke, Terrence R TR. 2003-06-19 Utilization of a beta-aminophosphotyrosyl mimetic in the design and synthesis of macrocyclic Grb2 SH2 domain-binding peptides. [PMID:12801226]
7. Song, Yan-Li YL, Roller, Peter P PP and Long, Ya-Qiu YQ. 2004-06-21 Development of l-3-aminotyrosine suitably protected for the synthesis of a novel nonphosphorylated hexapeptide with low-nanomolar Grb2-SH2 domain-binding affinity. [PMID:15149676]
8. Song, Yan-Li YL and 5 more authors. 2006-03-09 Discovery of a novel nonphosphorylated pentapeptide motif displaying high affinity for Grb2-SH2 domain by the utilization of 3'-substituted tyrosine derivatives. [PMID:16509576]
9. Jiang, Sheng S and 8 more authors. 2009-05-15 Discovery of thioether-bridged cyclic pentapeptides binding to Grb2-SH2 domain with high affinity. [PMID:19362470]

(5S,8S,14S)-14-(2-amino-2-oxoethyl)-5-(2-carboxyethyl)-1-(9H-fluoren-9-yl)-8-(4-hydroxybenzyl)-11,11-dimethyl-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source