(2S,3aR,9bR)-7,8-dihydroxy-2-propyl-6-((3-(trifluoromethyl)benzyl)oxy)-3,3a-dihydro-2H-furo[3,2-c]isochromen-5(9bH)-one

ID: ALA4874441

PubChem CID: 164627379

Max Phase: Preclinical

Molecular Formula: C22H21F3O6

Molecular Weight: 438.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC[C@H]1C[C@H]2OC(=O)c3c(cc(O)c(O)c3OCc3cccc(C(F)(F)F)c3)[C@H]2O1

Standard InChI:  InChI=1S/C22H21F3O6/c1-2-4-13-8-16-19(30-13)14-9-15(26)18(27)20(17(14)21(28)31-16)29-10-11-5-3-6-12(7-11)22(23,24)25/h3,5-7,9,13,16,19,26-27H,2,4,8,10H2,1H3/t13-,16+,19+/m0/s1

Standard InChI Key:  VXDPAPFCOAHDCI-URKNILKWSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   15.5230   -8.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5219   -9.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2367   -9.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2349   -8.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9503   -8.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9491   -9.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3818   -8.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6643   -8.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3807   -9.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6622   -9.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8312  -10.7647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6541  -10.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9936  -10.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6643   -7.4722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0911   -9.1247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0745  -10.5372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0639  -11.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8888  -11.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2986  -12.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2324   -7.4787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8085   -8.3040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8072   -9.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9457   -7.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9432   -6.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6583   -5.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6562   -5.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9399   -4.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2244   -5.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2300   -5.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3696   -4.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0851   -5.0012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.9494   -3.8707    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.7744   -3.8707    0.0000 F   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  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
  8 14  2  0
  9 15  1  1
 10 16  1  1
 12 17  1  6
 17 18  1  0
 18 19  1  0
  4 20  1  0
  1 21  1  0
  2 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 26 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874441

   ---

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: 438.40

Molecular Weight (Monoisotopic): 438.1290

AlogP: 4.86

#Rotatable Bonds: 5

Polar Surface Area: 85.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: ┄

CX LogP: 4.71

CX LogD: 4.68

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: 1.11

References

1. Coronado L, Zhang XQ, Dorta D, Escala N, Pineda LM, Ng MG, Del Olmo E, Wang CY, Gu YC, Shao CL, Spadafora C..  (2021)  Semisynthesis, Antiplasmodial Activity, and Mechanism of Action Studies of Isocoumarin Derivatives.,  84  (5.0): [PMID:33979168] [10.1021/acs.jnatprod.0c01032]

Source

Source(1):

• Scientific Literature