2-{[2-(1-Hydroxymethyl-propylamino)-9-isopropyl-9H-purin-6-ylamino]-methyl}-phenol

ID: ALA1094304

Chembl Id: CHEMBL1094304

Cas Number: 500735-47-7

PubChem CID: 5494414

Max Phase: Preclinical

Molecular Formula: C19H26N6O2

Molecular Weight: 370.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Olomoucine Ii | Olomoucine II|500735-47-7|(R)-2-(((2-((1-Hydroxybutan-2-yl)amino)-9-isopropyl-9H-purin-6-yl)amino)methyl)phenol|2a0c|SCHEMBL786673|CHEMBL1094304|HMS3229J03|BDBM50366800|AKOS027322559|DB04662|NSC 736738|2-[[[2-[[(2R)-1-hydroxybutan-2-yl]amino]-9-propan-2-ylpurin-6-yl]amino]methyl]phenol|CK9|NS00070782|Q27095411|2-({[2-{[(1R)-1-(hydroxymethyl)propyl]amino}-9-(1-methylethyl)-9H-purin-6-yl]amino}methyl)phenol|2-{[(2-{[(1R)-1-(HYDROXYMETHYL)PROPYL]AMINO}-9-ISOPROPYL-9H-PURIN-6-YL)AMINShow More⌵

Canonical SMILES:  CC[C@H](CO)Nc1nc(NCc2ccccc2O)c2ncn(C(C)C)c2n1

Standard InChI:  InChI=1S/C19H26N6O2/c1-4-14(10-26)22-19-23-17(20-9-13-7-5-6-8-15(13)27)16-18(24-19)25(11-21-16)12(2)3/h5-8,11-12,14,26-27H,4,9-10H2,1-3H3,(H2,20,22,23,24)/t14-/m1/s1

Standard InChI Key:  NDUVSANREQEDRE-CQSZACIVSA-N

Alternative Forms

1. Parent:

   

   ALA1094304

   OLOMOUCINE II

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: 370.46

Molecular Weight (Monoisotopic): 370.2117

AlogP: 2.91

#Rotatable Bonds: 8

Polar Surface Area: 108.12

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: 5.20

CX LogP: 2.59

CX LogD: 2.58

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -0.56

References

1. Krystof V, Lenobel R, Havlícek L, Kuzma M, Strnad M..  (2002)  Synthesis and biological activity of olomoucine II.,  12  (22): [PMID:12392733] [10.1016/s0960-894x(02)00693-5]

2. Smejkal K, Svacinová J, Slapetová T, Schneiderová K, Dall'acqua S, Innocenti G, Závalová V, Kollár P, Chudík S, Marek R, Julínek O, Urbanová M, Kartal M, Csöllei M, Dolezal K..  (2010)  Cytotoxic activities of several geranyl-substituted flavanones.,  73  (4): [PMID:20192247] [10.1021/np900681y]

3. Liang M, Tarr TB, Bravo-Altamirano K, Valdomir G, Rensch G, Swanson L, DeStefino NR, Mazzarisi CM, Olszewski RA, Wilson GM, Meriney SD, Wipf P..  (2012)  Synthesis and biological evaluation of a selective N- and p/q-type calcium channel agonist.,  3  (12): [PMID:24936234] [10.1021/ml3002083]

4. Zatloukal M, Jorda R, Gucký T, Řezníčková E, Voller J, Pospíšil T, Malínková V, Adamcová H, Kryštof V, Strnad M..  (2013)  Synthesis and in vitro biological evaluation of 2,6,9-trisubstituted purines targeting multiple cyclin-dependent kinases.,  61  [PMID:22770608] [10.1016/j.ejmech.2012.06.036]

5. Řezníčková E, Popa A, Gucký T, Zatloukal M, Havlíček L, Bazgier V, Berka K, Jorda R, Popa I, Nasereddin A, Jaffe CL, Kryštof V, Strnad M..  (2015)  2,6,9-Trisubstituted purines as CRK3 kinase inhibitors with antileishmanial activity in vitro.,  25  (11): [PMID:25937014] [10.1016/j.bmcl.2015.04.030]

6. Hazlitt RA, Teitz T, Bonga JD, Fang J, Diao S, Iconaru L, Yang L, Goktug AN, Currier DG, Chen T, Rankovic Z, Min J, Zuo J..  (2018)  Development of Second-Generation CDK2 Inhibitors for the Prevention of Cisplatin-Induced Hearing Loss.,  61  (17): [PMID:30091915] [10.1021/acs.jmedchem.8b00669]

Source

Source(1):

• Scientific Literature