2-phenyl-5,7-dihydroxy-8-(2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)-4H-chromen-4-one

ID: ALA4296686

PubChem CID: 66934034

Max Phase: Preclinical

Molecular Formula: C21H22ClNO5

Molecular Weight: 367.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@@H](c2c(O)cc(O)c3c(=O)cc(-c4ccccc4)oc23)[C@@H]1CO.Cl

Standard InChI:  InChI=1S/C21H21NO5.ClH/c1-22-8-7-13(14(22)11-23)19-15(24)9-16(25)20-17(26)10-18(27-21(19)20)12-5-3-2-4-6-12;/h2-6,9-10,13-14,23-25H,7-8,11H2,1H3;1H/t13-,14+;/m1./s1

Standard InChI Key:  QUQSBMYCYZBVNI-DFQHDRSWSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.8247   -7.9870    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.3773   -4.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3762   -5.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0910   -5.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0892   -3.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8045   -4.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8034   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5203   -5.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2429   -5.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2441   -4.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5226   -3.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5227   -3.0034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9523   -5.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9485   -6.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6610   -6.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3776   -6.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3773   -5.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6643   -5.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0867   -3.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6614   -5.4891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0956   -6.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4281   -6.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6827   -7.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5078   -7.5847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7628   -6.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9925   -8.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5475   -6.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1604   -7.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  9 13  1  0
  5 19  1  0
  3 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 21  4  1  1
 24 26  1  0
 25 27  1  6
 27 28  1  0
M  END

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: 367.40

Molecular Weight (Monoisotopic): 367.1420

AlogP: 2.65

#Rotatable Bonds: 3

Polar Surface Area: 94.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.60

CX Basic pKa: 7.42

CX LogP: 1.80

CX LogD: 1.72

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: 1.40

References

1. Hole AJ, Baumli S, Shao H, Shi S, Huang S, Pepper C, Fischer PM, Wang S, Endicott JA, Noble ME..  (2013)  Comparative structural and functional studies of 4-(thiazol-5-yl)-2-(phenylamino)pyrimidine-5-carbonitrile CDK9 inhibitors suggest the basis for isotype selectivity.,  56  (3): [PMID:23252711] [10.1021/jm301495v]

Source

Source(1):

• Scientific Literature