Thiophene-2-carboxylic acid (5R,5aR,8aR)-9-[3-((R)-methoxy)-4,5-dimethoxy-phenyl]-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

ID: ALA4867624

PubChem CID: 164625108

Max Phase: Preclinical

Molecular Formula: C27H24O9S

Molecular Weight: 524.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@H](OC(=O)c3cccs3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C27H24O9S/c1-30-19-7-13(8-20(31-2)25(19)32-3)22-14-9-17-18(35-12-34-17)10-15(14)24(16-11-33-27(29)23(16)22)36-26(28)21-5-4-6-37-21/h4-10,16,22-24H,11-12H2,1-3H3/t16-,22+,23-,24-/m0/s1

Standard InChI Key:  XINUGUXSINPSAG-ZFIFVKQDSA-N

Molfile:  

 
     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    8.9527   -6.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9509   -5.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6662   -5.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6650   -6.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3818   -6.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3842   -5.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2380   -6.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2392   -5.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4513   -5.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9631   -6.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4493   -6.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1056   -5.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1022   -6.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8917   -6.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3829   -6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8969   -5.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1434   -7.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3842   -4.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6699   -3.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3808   -7.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -8.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6654   -8.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3799   -9.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0971   -8.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0950   -8.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3800  -10.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6656  -10.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124   -9.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8144  -10.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9503   -9.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -8.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3152   -4.8243    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3110   -7.2532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9555   -4.3820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6699   -3.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3374   -2.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0825   -1.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2575   -1.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0027   -2.6607    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  4  2  0
  3  2  2  0
  2  8  1  0
  3  4  1  0
  3  6  1  0
  4  5  1  0
  5 13  1  0
 12  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 16  1  0
 14 17  2  0
  6 18  1  6
 18 19  1  0
  5 20  1  6
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 24 28  1  0
 28 29  1  0
 22 30  1  0
 30 31  1  0
 12 32  1  6
 13 33  1  1
 19 34  2  0
 19 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4867624

   ---

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: 524.55

Molecular Weight (Monoisotopic): 524.1141

AlogP: 4.34

#Rotatable Bonds: 6

Polar Surface Area: 98.75

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.44

Np Likeness Score: 0.83

References

1. Zhao Y, Li D, Wei M, Du R, Yan Z..  (2021)  The ester derivatives obtained by C-ring modification of podophyllotoxin induce apoptosis and inhibited proliferation in PC-3M cells via down-regulation of PI3K/Akt signaling pathway.,  46  [PMID:34098082] [10.1016/j.bmcl.2021.128174]

Source

Source(1):

• Scientific Literature