(1-(8-(((S)-1-((2S,4R)-4-Hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-8-oxooctyl)-1H-1,2,3-triazol-4-yl)methyl (4-((2-aminophenyl)carbamoyl)benzyl)carbamate

ID: ALA5188888

PubChem CID: 168281947

Max Phase: Preclinical

Molecular Formula: C48H60N10O7S

Molecular Weight: 921.14

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: Cc1ncsc1-c1ccc(CNC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)CCCCCCCn2cc(COC(=O)NCc3ccc(C(=O)Nc4ccccc4N)cc3)nn2)C(C)(C)C)cc1

Standard InChI: InChI=1S/C48H60N10O7S/c1-31-42(66-30-52-31)34-19-15-32(16-20-34)25-50-45(62)40-24-37(59)28-58(40)46(63)43(48(2,3)4)54-41(60)14-8-6-5-7-11-23-57-27-36(55-56-57)29-65-47(64)51-26-33-17-21-35(22-18-33)44(61)53-39-13-10-9-12-38(39)49/h9-10,12-13,15-22,27,30,37,40,43,59H,5-8,11,14,23-26,28-29,49H2,1-4H3,(H,50,62)(H,51,64)(H,53,61)(H,54,60)/t37-,40+,43-/m1/s1

Standard InChI Key: UKACPSCAHLUGEE-AKCINUCUSA-N

Molfile:

 
     RDKit          2D

 66 71  0  0  0  0  0  0  0  0999 V2000
   -0.3445   -0.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804   -0.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -0.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181   -0.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1305    0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9556    0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682    1.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1932    1.1888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9556    1.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058    0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4308    0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1932   -0.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -0.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -0.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7807   -0.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433    1.1888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433   -0.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5079    1.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1208    2.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8350    2.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6635    1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1208    3.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2468    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0438    0.9051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0333   -0.1052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168   -0.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4138   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4222    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6275    0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0059   -0.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7948   -0.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9996   -1.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8028    0.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0983    0.9337    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9219    0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1353    0.0940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4436   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4436   -1.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570   -1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -1.6691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -2.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8512   -2.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8512   -1.2568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.0020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5657   -2.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2802   -2.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9948   -2.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7092   -2.0815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9948   -3.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4237   -2.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1383   -2.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8530   -2.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5650   -2.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5650   -1.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8548   -0.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1383   -1.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2796   -0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9941   -1.2565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2796   -0.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7085   -0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4232   -1.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1353   -0.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1353   -0.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4250    0.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7085   -0.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4232   -2.0814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
 10  8  1  6
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 11 17  2  0
 18 16  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 16  1  0
 19 22  1  6
 21 23  1  1
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 29 27  2  0
 28 29  1  0
 30 28  2  0
 31 30  1  0
 32 31  2  0
 27 32  1  0
 30 33  1  0
 34 33  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 33  2  0
 37 38  1  0
  1 39  1  0
 39 40  1  0
 41 40  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 40  1  0
 42 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 47 49  2  0
 48 50  1  0
 50 51  1  0
 52 51  2  0
 53 52  1  0
 54 53  2  0
 55 54  1  0
 56 55  2  0
 51 56  1  0
 54 57  1  0
 57 58  1  0
 57 59  2  0
 58 60  1  0
 61 60  2  0
 62 61  1  0
 63 62  2  0
 64 63  1  0
 65 64  2  0
 60 65  1  0
 61 66  1  0
M  END

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type:	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:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 921.14	Molecular Weight (Monoisotopic): 920.4367	AlogP: 6.12	#Rotatable Bonds: 20
Polar Surface Area: 235.79	Molecular Species: NEUTRAL	HBA: 13	HBD: 6
#RO5 Violations: 4	HBA (Lipinski): 17	HBD (Lipinski): 7	#RO5 Violations (Lipinski): 4
CX Acidic pKa: 12.53	CX Basic pKa: 3.27	CX LogP: 4.33	CX LogD: 4.33
Aromatic Rings: 5	Heavy Atoms: 66	QED Weighted: 0.04	Np Likeness Score: -0.89

References

1. Cross JM, Coulson ME, Smalley JP, Pytel WA, Ismail O, Trory JS, Cowley SM, Hodgkinson JT.. (2022) A 'click' chemistry approach to novel entinostat (MS-275) based class I histone deacetylase proteolysis targeting chimeras., 13 (12.0): [PMID:36545434] [10.1039/d2md00199c]

(1-(8-(((S)-1-((2S,4R)-4-Hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-8-oxooctyl)-1H-1,2,3-triazol-4-yl)methyl (4-((2-aminophenyl)carbamoyl)benzyl)carbamate

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source