N1-(4-(2-(((2S,4R)-1-((S)-2-Acetamido-3,3-dimethylbutanoyl)-4-hydroxypyrrolidine-2-carboxamido)methyl)-5-(4-methylthiazol-5-yl)phenoxy)butyl)-N6-(4-((2-aminophenyl)carbamoyl)phenyl)-adipamide

ID: ALA5082910

PubChem CID: 166628887

Max Phase: Preclinical

Molecular Formula: C47H60N8O8S

Molecular Weight: 897.11

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC(=O)N[C@@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)NCc1ccc(-c2scnc2C)cc1OCCCCNC(=O)CCCCC(=O)Nc1ccc(C(=O)Nc2ccccc2N)cc1)C(C)(C)C

Standard InChI: InChI=1S/C47H60N8O8S/c1-29-42(64-28-51-29)32-16-17-33(26-50-45(61)38-25-35(57)27-55(38)46(62)43(47(3,4)5)52-30(2)56)39(24-32)63-23-11-10-22-49-40(58)14-8-9-15-41(59)53-34-20-18-31(19-21-34)44(60)54-37-13-7-6-12-36(37)48/h6-7,12-13,16-21,24,28,35,38,43,57H,8-11,14-15,22-23,25-27,48H2,1-5H3,(H,49,58)(H,50,61)(H,52,56)(H,53,59)(H,54,60)/t35-,38+,43+/m1/s1

Standard InChI Key: DMMLGYWZMDZZME-ZKUFXMFWSA-N

Molfile:

 
     RDKit          2D

 64 68  0  0  0  0  0  0  0  0999 V2000
    2.7827   -0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    0.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2116   -0.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9208    0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6405   -0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6506   -0.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414   -1.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219   -0.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517   -2.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903   -2.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -3.3873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800   -3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6252   -2.5892    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9105    1.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6199    1.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396    1.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3498    0.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0488    1.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.3002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3510    1.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9297    2.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1248    2.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2558    3.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9882    0.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3820   -0.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7760    0.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9576   -0.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -1.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3514   -1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7454   -0.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3821    0.8098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1700    0.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7762    1.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3516   -0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632    0.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3539   -0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6342    0.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749   -0.1126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    0.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048    1.1158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -0.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9328   -0.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6523    0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3616   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3513   -0.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812    0.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7905   -0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7802   -1.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4894   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2092   -1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9184   -1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9081   -2.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6380   -1.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3473   -1.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3370   -2.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6174   -2.6945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0463   -2.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7659   -2.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7762   -1.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0669   -1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2194   -0.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5101    0.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  2  0
  4  5  1  0
  6  5  2  0
  7  6  1  0
  3  8  1  0
  8  7  2  0
  9  7  1  0
 10  9  2  0
 11 10  1  0
 12 10  1  0
 13 12  2  0
 14 13  1  0
 14  9  1  0
  4 15  1  0
 15 16  1  0
 17 16  1  0
 17 18  2  0
 19 17  1  6
 20 19  1  0
 20 21  1  0
 22 21  1  0
 19 23  1  0
 23 22  1  0
 22 24  1  1
 25 20  1  0
 25 26  2  0
 27 25  1  6
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 32 27  1  0
 33 32  1  0
 33 34  1  0
 33 35  2  0
  1 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  2  0
 40 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 47 46  2  0
 48 46  1  0
 49 48  1  0
 49 50  2  0
 50 51  1  0
 51 52  2  0
 53 52  1  0
 53 54  2  0
 53 55  1  0
 56 55  1  0
 56 57  2  0
 58 57  1  0
 57 59  1  0
 59 60  2  0
 60 61  1  0
 61 62  2  0
 56 62  1  0
 52 63  1  0
 63 64  2  0
 49 64  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: Unknown	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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 897.11	Molecular Weight (Monoisotopic): 896.4255	AlogP: 5.56	#Rotatable Bonds: 20
Polar Surface Area: 234.18	Molecular Species: NEUTRAL	HBA: 11	HBD: 7
#RO5 Violations: 4	HBA (Lipinski): 16	HBD (Lipinski): 8	#RO5 Violations (Lipinski): 4
CX Acidic pKa: 12.34	CX Basic pKa: 3.24	CX LogP: 2.52	CX LogD: 2.52
Aromatic Rings: 4	Heavy Atoms: 64	QED Weighted: 0.04	Np Likeness Score: -0.79

References

1. Smalley JP, Baker IM, Pytel WA, Lin LY, Bowman KJ, Schwabe JWR, Cowley SM, Hodgkinson JT.. (2022) Optimization of Class I Histone Deacetylase PROTACs Reveals that HDAC1/2 Degradation is Critical to Induce Apoptosis and Cell Arrest in Cancer Cells., 65 (7.0): [PMID:35293758] [10.1021/acs.jmedchem.1c02179]

N1-(4-(2-(((2S,4R)-1-((S)-2-Acetamido-3,3-dimethylbutanoyl)-4-hydroxypyrrolidine-2-carboxamido)methyl)-5-(4-methylthiazol-5-yl)phenoxy)butyl)-N6-(4-((2-aminophenyl)carbamoyl)phenyl)-adipamide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source