(R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (Z)-4-(3-fluoro-4-methylphenyl)-4-oxobut-2-enoate

ID: ALA4571687

PubChem CID: 155562472

Max Phase: Preclinical

Molecular Formula: C27H23FO7

Molecular Weight: 478.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CC[C@@H](OC(=O)/C=C\C(=O)c1ccc(C)c(F)c1)C1=CC(=O)c2c(O)ccc(O)c2C1=O

Standard InChI:  InChI=1S/C27H23FO7/c1-14(2)4-10-23(17-13-22(32)25-20(30)7-8-21(31)26(25)27(17)34)35-24(33)11-9-19(29)16-6-5-15(3)18(28)12-16/h4-9,11-13,23,30-31H,10H2,1-3H3/b11-9-/t23-/m1/s1

Standard InChI Key:  TZMRIHASUCILER-VLRJHWBUSA-N

Molfile:  

 
     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   35.0924  -16.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0913  -17.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7993  -18.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7975  -16.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5061  -16.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5069  -17.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2154  -18.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9237  -17.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9190  -16.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2099  -16.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2055  -15.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2171  -18.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6242  -16.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3344  -16.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0396  -16.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7497  -16.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7547  -17.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4550  -16.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6192  -15.5531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3244  -15.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3194  -14.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0346  -15.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0246  -13.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7951  -15.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8012  -18.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7348  -14.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4400  -13.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7398  -15.1316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.1476  -14.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8523  -13.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8478  -13.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1326  -12.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4308  -13.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1248  -11.8590    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   43.5524  -12.6664    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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  1  0
 10 11  2  0
  7 12  2  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 13 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
  4 24  1  0
  3 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 27  1  0
 32 34  1  0
 31 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4571687

   ---

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: 478.47

Molecular Weight (Monoisotopic): 478.1428

AlogP: 4.56

#Rotatable Bonds: 7

Polar Surface Area: 117.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 6.28

CX LogD: 6.25

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.20

Np Likeness Score: 1.08

References

1. Sun WX, Han HW, Yang MK, Wen ZL, Wang YS, Fu JY, Lu YT, Wang MY, Bao JX, Lu GH, Qi JL, Wang XM, Lin HY, Yang YH..  (2019)  Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR.,  27  (23): [PMID:31648877] [10.1016/j.bmc.2019.115153]

Source

Source(1):

• Scientific Literature