4-hydroxy-3-(2-(4-hydroxyphenyl)-2-oxo-1-(piperidin-1-yl)ethyl)-2H-chromen-2-one

ID: ALA4571358

PubChem CID: 155562811

Max Phase: Preclinical

Molecular Formula: C22H21NO5

Molecular Weight: 379.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(O)cc1)C(c1c(O)c2ccccc2oc1=O)N1CCCCC1

Standard InChI:  InChI=1S/C22H21NO5/c24-15-10-8-14(9-11-15)20(25)19(23-12-4-1-5-13-23)18-21(26)16-6-2-3-7-17(16)28-22(18)27/h2-3,6-11,19,24,26H,1,4-5,12-13H2

Standard InChI Key:  LOQIHCPOPNJLHC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.6022   -9.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3103   -9.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085   -7.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171   -8.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0159   -9.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7221   -9.4888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4340   -9.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4352   -8.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7244   -7.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7245   -7.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1406   -9.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1439   -7.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8506   -8.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1458   -7.0370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -9.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5593   -7.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2616   -8.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9698   -7.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9722   -7.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2605   -6.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5552   -7.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6804   -6.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8584   -6.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8624   -5.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1575   -5.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4470   -5.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4414   -6.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
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  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  2  0
  9 13  1  0
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 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 15 24  1  0
 15 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4571358

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 379.41

Molecular Weight (Monoisotopic): 379.1420

AlogP: 3.61

#Rotatable Bonds: 4

Polar Surface Area: 90.98

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.53

CX Basic pKa: 6.92

CX LogP: 1.24

CX LogD: 0.64

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -0.14

References

1. Singh H, Singh JV, Bhagat K, Gulati HK, Sanduja M, Kumar N, Kinarivala N, Sharma S..  (2019)  Rational approaches, design strategies, structure activity relationship and mechanistic insights for therapeutic coumarin hybrids.,  27  (16): [PMID:31255497] [10.1016/j.bmc.2019.06.033]

Source

Source(1):

• Scientific Literature