ID: ALA1096256

Max Phase: Preclinical

Molecular Formula: C12H13BrN4O3

Molecular Weight: 341.17

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN1C(=O)N[C@H]2[C@@H]3NC(=O)c4ccc(Br)n4[C@@H]3C[C@]21O

Standard InChI:  InChI=1S/C12H13BrN4O3/c1-16-11(19)15-9-8-6(4-12(9,16)20)17-5(10(18)14-8)2-3-7(17)13/h2-3,6,8-9,20H,4H2,1H3,(H,14,18)(H,15,19)/t6-,8-,9+,12+/m1/s1

Standard InChI Key:  MPASKXAEPUAMBS-WJOUQXRDSA-N

Molecule Features

Natural Product: Yes

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: 341.17

Molecular Weight (Monoisotopic): 340.0171

AlogP: 0.02

#Rotatable Bonds: 0

Polar Surface Area: 86.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.25

CX Basic pKa:

CX LogP: -0.32

CX LogD: -0.32

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: 1.97

References

1. Tilvi S, Moriou C, Martin MT, Gallard JF, Sorres J, Patel K, Petek S, Debitus C, Ermolenko L, Al-Mourabit A..  (2010)  Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha.,  73  (4): [PMID:20166736] [10.1021/np900539j]

2. Li Z, Shigeoka D, Caulfield TR, Kawachi T, Qiu Y, Kamon T, Arai M, Tun HW, Yoshimitsu T.  (2013)  An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses,  4  (7): [10.1039/C3MD00094J]

3. Li Z, Kamon T, Personett DA, Caulfield T, Copland JA, Yoshimitsu T, Tun HW.  (2012)  Pharmacokinetics of Agelastatin A in the central nervous system,  3  (2): [10.1039/C1MD00240F]

4. Stout EP, Choi MY, Castro JE, Molinski TF..  (2014)  Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies.,  57  (12): [PMID:24673739] [10.1021/jm4016922]

5. Stout EP, Choi MY, Castro JE, Molinski TF..  (2014)  Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies.,  57  (12): [PMID:24673739] [10.1021/jm4016922]

6. Jouanneau M, McClary B, Reyes JC, Chen R, Chen Y, Plunkett W, Cheng X, Milinichik AZ, Albone EF, Liu JO, Romo D..  (2016)  Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe.,  26  (8): [PMID:26951751] [10.1016/j.bmcl.2016.02.051]

7. Fan A, Sharp PP..  (2021)  Inhibitors of Eukaryotic Translational Machinery as Therapeutic Agents.,  64  (5.0): [PMID:33592144] [10.1021/acs.jmedchem.0c01746]

Source

Source(1):

• Scientific Literature