ID: ALA3774537

Max Phase: Preclinical

Molecular Formula: C23H23ClN6O

Molecular Weight: 434.93

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]cnc2c(-n3cc(CCN4CCC(c5cccc(Cl)c5)CC4)cn3)nccc12

Standard InChI:  InChI=1S/C23H23ClN6O/c24-19-3-1-2-18(12-19)17-6-10-29(11-7-17)9-5-16-13-28-30(14-16)22-21-20(4-8-25-22)23(31)27-15-26-21/h1-4,8,12-15,17H,5-7,9-11H2,(H,26,27,31)

Standard InChI Key:  LDSDVQOOEYCWQS-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 434.93

Molecular Weight (Monoisotopic): 434.1622

AlogP: 3.58

#Rotatable Bonds: 5

Polar Surface Area: 79.70

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.07

CX Basic pKa: 9.00

CX LogP: 3.00

CX LogD: 1.64

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -1.44

References

1. Bavetsias V, Lanigan RM, Ruda GF, Atrash B, McLaughlin MG, Tumber A, Mok NY, Le Bihan YV, Dempster S, Boxall KJ, Jeganathan F, Hatch SB, Savitsky P, Velupillai S, Krojer T, England KS, Sejberg J, Thai C, Donovan A, Pal A, Scozzafava G, Bennett JM, Kawamura A, Johansson C, Szykowska A, Gileadi C, Burgess-Brown NA, von Delft F, Oppermann U, Walters Z, Shipley J, Raynaud FI, Westaway SM, Prinjha RK, Fedorov O, Burke R, Schofield CJ, Westwood IM, Bountra C, Müller S, van Montfort RL, Brennan PE, Blagg J..  (2016)  8-Substituted Pyrido[3,4-d]pyrimidin-4(3H)-one Derivatives As Potent, Cell Permeable, KDM4 (JMJD2) and KDM5 (JARID1) Histone Lysine Demethylase Inhibitors.,  59  (4): [PMID:26741168] [10.1021/acs.jmedchem.5b01635]

2. Le Bihan YV, Lanigan RM, Atrash B, McLaughlin MG, Velupillai S, Malcolm AG, England KS, Ruda GF, Mok NY, Tumber A, Tomlin K, Saville H, Shehu E, McAndrew C, Carmichael L, Bennett JM, Jeganathan F, Eve P, Donovan A, Hayes A, Wood F, Raynaud FI, Fedorov O, Brennan PE, Burke R, van Montfort RLM, Rossanese OW, Blagg J, Bavetsias V..  (2019)  C8-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones: Studies towards the identification of potent, cell penetrant Jumonji C domain containing histone lysine demethylase 4 subfamily (KDM4) inhibitors, compound profiling in cell-based target engagement assays.,  177  [PMID:31158747] [10.1016/j.ejmech.2019.05.041]

3. Wu Q, Young B, Wang Y, Davidoff AM, Rankovic Z, Yang J..  (2022)  Recent Advances with KDM4 Inhibitors and Potential Applications.,  65  (14.0): [PMID:35838529] [10.1021/acs.jmedchem.2c00680]

Source

Source(1):

• Scientific Literature