(2R,4S)-1-(4-(4-(3,4-dichlorophenyl)thiazol-2-ylamino)phenethyl)-2-(hydroxymethyl)piperidin-4-ol

ID: ALA2409865

Chembl Id: CHEMBL2409865

Cas Number: 1448706-15-7

PubChem CID: 71627420

Max Phase: Preclinical

Molecular Formula: C23H25Cl2N3O2S

Molecular Weight: 478.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1C[C@@H](O)CCN1CCc1ccc(Nc2nc(-c3ccc(Cl)c(Cl)c3)cs2)cc1

Standard InChI:  InChI=1S/C23H25Cl2N3O2S/c24-20-6-3-16(11-21(20)25)22-14-31-23(27-22)26-17-4-1-15(2-5-17)7-9-28-10-8-19(30)12-18(28)13-29/h1-6,11,14,18-19,29-30H,7-10,12-13H2,(H,26,27)/t18-,19+/m1/s1

Standard InChI Key:  SQJKFWCRPARYPY-MOPGFXCFSA-N

Alternative Forms

1. Parent:

   

   ALA2409865

   (2r,4s)-1-[2-(4-{[4-(3,4-Dichlorophenyl)-1,3-Thiazol-2-Yl]amino}phenyl)ethyl]-2-(Hydroxymethyl)piperidin-4-Ol

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

Calculated Properties

Molecular Weight: 478.45

Molecular Weight (Monoisotopic): 477.1045

AlogP: 5.22

#Rotatable Bonds: 7

Polar Surface Area: 68.62

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.55

CX Basic pKa: 8.88

CX LogP: 4.92

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.12

References

1. Gustin DJ, Li Y, Brown ML, Min X, Schmitt MJ, Wanska M, Wang X, Connors R, Johnstone S, Cardozo M, Cheng AC, Jeffries S, Franks B, Li S, Shen S, Wong M, Wesche H, Xu G, Carlson TJ, Plant M, Morgenstern K, Rex K, Schmitt J, Coxon A, Walker N, Kayser F, Wang Z..  (2013)  Structure guided design of a series of sphingosine kinase (SphK) inhibitors.,  23  (16): [PMID:23845219] [10.1016/j.bmcl.2013.06.030]

2. Zhang S, Chen X, Wu C, Xu H, Xie X, Feng M, Hu S, Bai H, Gao F, Tong L, Ding J, Liu H, Xie Z, Wang J..  (2022)  Novel Sphingosine Kinase 1 Inhibitor Suppresses Growth of Solid Tumor and Inhibits the Lung Metastasis of Triple-Negative Breast Cancer.,  65  (11.0): [PMID:35439002] [10.1021/acs.jmedchem.2c00040]

Source

Source(1):

• Scientific Literature