(S)-4-(7-methoxy-6-(3-methylbut-2-enyl)-4-oxochroman-2-yl)phenyl acetate

ID: ALA4173504

PubChem CID: 145949721

Max Phase: Preclinical

Molecular Formula: C23H24O5

Molecular Weight: 380.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1CC=C(C)C)C(=O)C[C@@H](c1ccc(OC(C)=O)cc1)O2

Standard InChI:  InChI=1S/C23H24O5/c1-14(2)5-6-17-11-19-20(25)12-22(28-23(19)13-21(17)26-4)16-7-9-18(10-8-16)27-15(3)24/h5,7-11,13,22H,6,12H2,1-4H3/t22-/m0/s1

Standard InChI Key:  MEVNIJPFUHFUKV-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   36.2480  -19.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5190  -21.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5179  -22.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2326  -22.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2308  -21.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9463  -21.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9451  -22.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6619  -22.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3846  -22.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3858  -21.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6643  -20.9991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8044  -21.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6596  -23.4902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0995  -21.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8133  -21.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5282  -21.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5308  -20.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8123  -19.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1002  -20.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8031  -22.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0890  -22.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3741  -22.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6601  -22.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3735  -23.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8042  -20.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9627  -20.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6769  -19.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9633  -21.0131    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  1  0
 10 11  1  0
  2 12  1  0
  8 13  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 10 14  1  6
 17  1  1  0
  3 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 12 25  1  0
  1 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173504

   ---

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 380.44

Molecular Weight (Monoisotopic): 380.1624

AlogP: 4.84

#Rotatable Bonds: 5

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: 1.44

References

1. Gupta N, Qayum A, Raina A, Shankar R, Gairola S, Singh S, Sangwan PL..  (2018)  Synthesis and biological evaluation of novel bavachinin analogs as anticancer agents.,  145  [PMID:29335212] [10.1016/j.ejmech.2018.01.006]

Source

Source(1):

• Scientific Literature