(1-(10-(((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)-10-oxodecyl)-1H-1,2,3-triazol-4-yl)methyl (4-((2-aminophenyl) carbamoyl)benzyl)carbamate

ID: ALA5181179

PubChem CID: 168276405

Max Phase: Preclinical

Molecular Formula: C50H64N10O7S

Molecular Weight: 949.19

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)CCCCCCCCCn2cc(COC(=O)NCc3ccc(C(=O)Nc4ccccc4N)cc3)nn2)C(C)(C)C)cc1

Standard InChI: InChI=1S/C50H64N10O7S/c1-33-44(68-32-54-33)36-21-17-34(18-22-36)27-52-47(64)42-26-39(61)30-60(42)48(65)45(50(2,3)4)56-43(62)16-10-8-6-5-7-9-13-25-59-29-38(57-58-59)31-67-49(66)53-28-35-19-23-37(24-20-35)46(63)55-41-15-12-11-14-40(41)51/h11-12,14-15,17-24,29,32,39,42,45,61H,5-10,13,16,25-28,30-31,51H2,1-4H3,(H,52,64)(H,53,66)(H,55,63)(H,56,62)/t39-,42+,45-/m1/s1

Standard InChI Key: VCLKGDPCTKGOSX-BZPYCXPJSA-N

Molfile:

 
     RDKit          2D

 68 73  0  0  0  0  0  0  0  0999 V2000
    0.2742   -1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992   -1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7493    0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5743    0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    0.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8118    0.8316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244    0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0495    0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4620    0.8316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1266    1.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394    2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4535    1.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820    0.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8655    0.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6624    0.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6519   -0.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2353   -1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0322   -0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2460   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0407    0.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6243   -0.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4133   -1.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6181   -1.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4212   -0.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7167    0.5765    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.5402    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7537   -0.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0620   -0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0620   -1.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394    2.9618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4620   -0.5974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8118   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244   -1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993   -1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5743    1.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -2.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -2.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758   -1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -1.3118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6855   -1.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699   -1.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699   -0.8995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6855   -0.6447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844   -2.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8987   -1.7242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6134   -2.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3279   -1.7242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6134   -2.9618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0424   -2.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7569   -1.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4715   -2.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1835   -1.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1835   -0.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4733   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7569   -0.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8980   -0.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6125   -0.8993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8980    0.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3270   -0.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0417   -0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7537   -0.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7537    0.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0435    0.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3270    0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0417   -1.7241    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
  9  8  1  6
  9 10  1  0
 10 11  1  0
 12 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 15 16  1  1
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 20 25  1  0
 23 26  1  0
 27 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  2  0
 30 31  1  0
 13 32  1  6
 10 33  2  0
  9 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
  7 38  2  0
  1 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 43 42  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 46 42  1  0
 44 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 49 51  2  0
 50 52  1  0
 52 53  1  0
 54 53  2  0
 55 54  1  0
 56 55  2  0
 57 56  1  0
 58 57  2  0
 53 58  1  0
 56 59  1  0
 59 60  1  0
 59 61  2  0
 60 62  1  0
 63 62  2  0
 64 63  1  0
 65 64  2  0
 66 65  1  0
 67 66  2  0
 62 67  1  0
 63 68  1  0
M  END

Associated Targets(Human)

HDAC1 Tclin VHL/Histone deacetylase 1 (90 Activities)

Discover Target: HDAC1

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

HDAC2 Tclin VHL/Histone deacetylase 2 (81 Activities)

Discover Target: HDAC2

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

HDAC3 Tclin VHL/Histone deacetylase 3 (77 Activities)

Discover Target: HDAC3

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:	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: 949.19	Molecular Weight (Monoisotopic): 948.4680	AlogP: 6.90	#Rotatable Bonds: 22
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: 12.68	CX Basic pKa: 3.27	CX LogP: 5.22	CX LogD: 5.22
Aromatic Rings: 5	Heavy Atoms: 68	QED Weighted: 0.03	Np Likeness Score: -0.86

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-(10-(((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)-10-oxodecyl)-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