ID: ALA574737

Max Phase: Phase

Molecular Formula: C28H26N4O4

Molecular Weight: 482.54

Molecule Type: Small molecule

Representations

Synonyms (8): 7-hydroxystaurosporine | Ucn 01 | Ucn-01 | KRX-0601 | KW-2401 | NSC-638850 | UCN-01 | UCN-02
Synonyms from Alternative Forms(8):

Canonical SMILES:  CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)N[C@H]4O

Standard InChI:  InChI=1S/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18-,25-,27+,28+/m1/s1

Standard InChI Key:  PBCZSGKMGDDXIJ-KRUBCLEUSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 482.54

Molecular Weight (Monoisotopic): 482.1954

AlogP: 3.84

#Rotatable Bonds: 2

Polar Surface Area: 89.68

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.80

CX Basic pKa: 9.52

CX LogP: 3.41

CX LogD: 1.49

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.36

Np Likeness Score: 1.42

References

1. Fabre S, Prudhomme M, Rapp M.  (1992)  Preparation of synthons for the synthesis of protein kinase C inhibitors from rebeccamycin.,  2  (5): [10.1016/S0960-894X(00)80167-5]

2. Fabre S, Prudhomme M, Rapp M.  (1992)  Preparation of synthons for the synthesis of protein kinase C inhibitors from rebeccamycin.,  2  (5): [10.1016/S0960-894X(00)80167-5]

3. Bain J, Plater L, Elliott M, Shpiro N, Hastie CJ, McLauchlan H, Klevernic I, Arthur JS, Alessi DR, Cohen P..  (2007)  The selectivity of protein kinase inhibitors: a further update.,  408  (3): [PMID:17850214] [10.1042/bj20070797]

4. Oza V, Ashwell S, Brassil P, Breed J, Deng C, Ezhuthachan J, Haye H, Horn C, Janetka J, Lyne P, Newcombe N, Otterbien L, Pass M, Read J, Roswell S, Su M, Toader D, Yu D, Yu Y, Valentine A, Webborn P, White A, Zabludoff S, Zheng X..  (2010)  Discovery of a novel class of triazolones as checkpoint kinase inhibitors--hit to lead exploration.,  20  (17): [PMID:20673630] [10.1016/j.bmcl.2010.07.015]

5. Sako Y, Ichikawa S, Osada A, Matsuda A..  (2010)  Synthesis and evaluation of 5-substituted 9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as check point 1 kinase inhibitors.,  18  (22): [PMID:20943405] [10.1016/j.bmc.2010.09.042]

6. Phosrithong N, Ungwitayatorn J.  (2010)  Molecular docking study on anticancer activity of plant-derived natural products,  19  (8): [10.1007/s00044-009-9233-5]

7. Unpublished dataset, 

8. Klaeger S, Heinzlmeir S and Wilhelm M et al.  (2017)  The target landscape of clinical kinase drugs.,  358  (6367): [PMID:29191878] [10.1126/science.aan4368]

9. Heffron TP..  (2016)  Small Molecule Kinase Inhibitors for the Treatment of Brain Cancer.,  59  (22): [PMID:27414067] [10.1021/acs.jmedchem.6b00618]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• Kuster lab chemical proteomics drug profiling