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

ID: ALA4529521

PubChem CID: 155545559

Max Phase: Preclinical

Molecular Formula: C28H26O7

Molecular Weight: 474.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1ccc(C(=O)/C=C\C(=O)O[C@H](CC=C(C)C)C2=CC(=O)c3c(O)ccc(O)c3C2=O)cc1

Standard InChI:  InChI=1S/C28H26O7/c1-4-17-6-8-18(9-7-17)20(29)12-14-25(33)35-24(13-5-16(2)3)19-15-23(32)26-21(30)10-11-22(31)27(26)28(19)34/h5-12,14-15,24,30-31H,4,13H2,1-3H3/b14-12-/t24-/m1/s1

Standard InChI Key:  XSUBICJCIGSEHS-PEBGULEFSA-N

Molfile:  

 
     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.5368  -17.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357  -18.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2437  -18.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419  -17.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9506  -17.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513  -18.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599  -18.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3681  -18.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634  -17.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6543  -16.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499  -16.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615  -19.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0686  -16.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7788  -17.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4840  -16.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1942  -17.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1991  -18.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8994  -16.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0636  -16.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688  -15.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7639  -14.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4790  -16.1636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4691  -14.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2395  -16.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2456  -19.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792  -14.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8845  -14.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1842  -15.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5920  -14.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2967  -14.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2922  -13.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5770  -13.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8752  -13.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9968  -13.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7076  -13.6889    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
 31 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529521

   ---

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: 474.51

Molecular Weight (Monoisotopic): 474.1679

AlogP: 4.67

#Rotatable Bonds: 8

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: 6.58

CX LogD: 6.55

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: 1.40

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