ethyl 3-(7-hydroxy-2-methyl-4-(3-nitrophenyl)-2H-chromen-2-yl)propanoate

ID: ALA3220142

PubChem CID: 90666857

Max Phase: Preclinical

Molecular Formula: C21H21NO6

Molecular Weight: 383.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CCC1(C)C=C(c2cccc([N+](=O)[O-])c2)c2ccc(O)cc2O1

Standard InChI:  InChI=1S/C21H21NO6/c1-3-27-20(24)9-10-21(2)13-18(14-5-4-6-15(11-14)22(25)26)17-8-7-16(23)12-19(17)28-21/h4-8,11-13,23H,3,9-10H2,1-2H3

Standard InChI Key:  PGTCINVGEATNJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.2000   -8.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -8.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6125   -8.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8931   -7.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943   -8.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -8.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812   -6.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -7.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -8.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433   -8.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263   -7.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501   -6.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7538   -5.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399   -5.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441   -4.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614   -4.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4759   -4.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -5.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6091   -8.4809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1975   -4.3553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082   -4.7742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049   -3.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -7.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -7.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500   -6.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500   -8.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -8.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -8.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
  7  4  1  0
 14 15  1  0
  8  9  1  0
 15 16  2  0
  2  1  1  0
 16 17  1  0
  4  5  2  0
 17 18  2  0
 18 13  1  0
 12 13  1  0
  3  2  1  0
  5 19  1  0
  5  6  1  0
  6  9  2  0
  8 12  1  0
 20 21  2  0
 20 22  1  0
 17 20  1  0
  9 10  1  0
  1 23  1  0
 10  2  1  0
 23 24  1  0
  2 11  1  0
 24 25  2  0
 11 12  2  0
 24 26  1  0
 26 27  1  0
  8  7  2  0
 27 28  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3220142

   Ethyl 3-[7-hydroxy-2-methyl-4-(3-nitrophenyl)chromen-2-yl]propanoate

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: 383.40

Molecular Weight (Monoisotopic): 383.1369

AlogP: 4.23

#Rotatable Bonds: 6

Polar Surface Area: 98.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.92

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.08

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 0.55

References

1. Oh S, Cho SW, Yang J, Sun HJ, Chung YS, Shin CS, Park SB.  (2011)  Discovery of a novel benzopyranyl compound as a potent in vitro and in vivo osteogenic agent,  2  (1): [10.1039/C0MD00149J]

Source

Source(1):

• Scientific Literature