ID: ALA1092481

Max Phase: Preclinical

Molecular Formula: C23H38ClN3O

Molecular Weight: 371.57

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCCCCCCCCCCc1ccc(C(=O)NC2(C(=N)N)CC2)cc1.Cl

Standard InChI:  InChI=1S/C23H37N3O.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-19-13-15-20(16-14-19)21(27)26-23(17-18-23)22(24)25;/h13-16H,2-12,17-18H2,1H3,(H3,24,25)(H,26,27);1H

Standard InChI Key:  APHADGNZJGOQKN-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: 371.57

Molecular Weight (Monoisotopic): 371.2937

AlogP: 5.35

#Rotatable Bonds: 14

Polar Surface Area: 78.97

Molecular Species: BASE

HBA: 2

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 11.11

CX LogP: 5.89

CX LogD: 3.49

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.23

Np Likeness Score: -0.20

References

1. Mathews TP, Kennedy AJ, Kharel Y, Kennedy PC, Nicoara O, Sunkara M, Morris AJ, Wamhoff BR, Lynch KR, Macdonald TL..  (2010)  Discovery, biological evaluation, and structure-activity relationship of amidine based sphingosine kinase inhibitors.,  53  (7): [PMID:20205392] [10.1021/jm901860h]

2. Kennedy AJ, Mathews TP, Kharel Y, Field SD, Moyer ML, East JE, Houck JD, Lynch KR, Macdonald TL..  (2011)  Development of amidine-based sphingosine kinase 1 nanomolar inhibitors and reduction of sphingosine 1-phosphate in human leukemia cells.,  54  (10): [PMID:21495716] [10.1021/jm2001053]

3. 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]

Source

Source(1):

• Scientific Literature