(13R,15S)-13-methyl-16-oxa-8,9,12,22,24-pentaazahexacyclo[15.6.2.1^{6,9}.1^{12,15}.0^{2,7}.0^{21,25}]heptacosa-1(24),2,4,6(27),7,17(25),18,20,22-nonaene-23,27-diol

ID: ALA215803

Chembl Id: CHEMBL215803

PubChem CID: 16046126

Max Phase: Preclinical

Molecular Formula: C22H21N5O3

Molecular Weight: 403.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]2CN1CCn1nc3c(cccc3c1O)-c1nc3c(cccc3nc1O)O2

Standard InChI:  InChI=1S/C22H21N5O3/c1-12-10-13-11-26(12)8-9-27-22(29)15-5-2-4-14(18(15)25-27)19-21(28)23-16-6-3-7-17(30-13)20(16)24-19/h2-7,12-13,29H,8-11H2,1H3,(H,23,28)/t12-,13+/m1/s1

Standard InChI Key:  PAXKGQZKOJPPEG-OLZOCXBDSA-N

Alternative Forms

1. Parent:

   

   ALA215803

   (13r,15s)-13-Methyl-16-Oxa-8,9,12,22,24-Pentaazahexacyclo[15.6.2.16,9.1,12,15.0,2,7.0,21,25]heptacosa-1(24),2,4,6,17(25),18,20-Heptaene-23,26-Dione

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: 403.44

Molecular Weight (Monoisotopic): 403.1644

AlogP: 2.91

#Rotatable Bonds: ┄

Polar Surface Area: 96.53

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.39

CX Basic pKa: 8.31

CX LogP: 2.41

CX LogD: 2.39

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.47

Np Likeness Score: -0.11

References

1. Kawanishi N, Sugimoto T, Shibata J, Nakamura K, Masutani K, Ikuta M, Hirai H..  (2006)  Structure-based drug design of a highly potent CDK1,2,4,6 inhibitor with novel macrocyclic quinoxalin-2-one structure.,  16  (19): [PMID:16876403] [10.1016/j.bmcl.2006.07.026]

2. Marsault E, Peterson ML..  (2011)  Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.,  54  (7): [PMID:21381769] [10.1021/jm1012374]

Source

Source(1):

• Scientific Literature