(5-Fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl(((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-5-yl)methyl)succinate

ID: ALA4538150

PubChem CID: 155548981

Max Phase: Preclinical

Molecular Formula: C24H27FN2O9

Molecular Weight: 506.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(COC(=O)CCC(=O)OCn1cc(F)c(=O)[nH]c1=O)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C24H27FN2O9/c1-13-15-6-5-14(4-3-9-24(2)20(36-24)19(15)35-22(13)31)11-33-17(28)7-8-18(29)34-12-27-10-16(25)21(30)26-23(27)32/h4,10,15,19-20H,1,3,5-9,11-12H2,2H3,(H,26,30,32)/b14-4+/t15-,19-,20-,24+/m0/s1

Standard InChI Key:  WRUCIFBOGNCBEM-JALKFBPJSA-N

Molfile:  

 
     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
   29.5569   -6.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9864   -5.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1682   -5.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8580   -7.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4687   -6.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1488   -7.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3210   -6.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1327   -6.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3027   -5.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5988   -4.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5462   -4.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7660   -4.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8683   -3.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0774   -3.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2582   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9615   -4.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5042   -5.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8892   -4.7052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.2680   -7.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9405   -6.0974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.9416   -8.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6504   -6.6719    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.6735   -3.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3769   -4.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6822   -2.9536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0889   -3.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7922   -4.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5042   -3.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7835   -5.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2075   -4.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9196   -3.8159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6241   -4.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3339   -3.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3468   -3.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6437   -2.6060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9276   -3.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2251   -2.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0604   -2.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0357   -4.2605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  1  0
  5  8  1  0
  7  6  1  0
  6  4  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2  7  1  0
 10 11  1  0
  3 12  1  0
 11 13  2  0
 12 14  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
  3 17  1  1
  2 18  1  1
  5 19  2  0
  8 20  1  6
  4 21  2  0
  7 22  1  1
 16 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 36  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 34 38  2  0
 33 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538150

   ---

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: 506.48

Molecular Weight (Monoisotopic): 506.1701

AlogP: 1.26

#Rotatable Bonds: 7

Polar Surface Area: 146.29

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.08

CX Basic pKa: ┄

CX LogP: 1.71

CX LogD: 1.63

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.19

Np Likeness Score: 1.48

References

1. Ding Y, Li S, Ge W, Liu Z, Zhang X, Wang M, Chen T, Chen Y, Zhang Q..  (2019)  Design and synthesis of parthenolide and 5-fluorouracil conjugates as potential anticancer agents against drug resistant hepatocellular carcinoma.,  183  [PMID:31553932] [10.1016/j.ejmech.2019.111706]

Source

Source(1):

• Scientific Literature