(((2-(3-((3-Fluoro-4-methoxyphenyl)carbamoyl)phenyl)-thieno[2,3-d]pyrimidin-4-yl)amino)methylene)bis-(phosphonic acid)

ID: ALA4577077

PubChem CID: 153290116

Max Phase: Preclinical

Molecular Formula: C21H19FN4O8P2S

Molecular Weight: 568.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)c2cccc(-c3nc(NC(P(=O)(O)O)P(=O)(O)O)c4ccsc4n3)c2)cc1F

Standard InChI:  InChI=1S/C21H19FN4O8P2S/c1-34-16-6-5-13(10-15(16)22)23-19(27)12-4-2-3-11(9-12)17-24-18(14-7-8-37-20(14)25-17)26-21(35(28,29)30)36(31,32)33/h2-10,21H,1H3,(H,23,27)(H,24,25,26)(H2,28,29,30)(H2,31,32,33)

Standard InChI Key:  XPPGEOUCUMGOGK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.1202  -12.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1174  -11.3545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087  -10.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9422  -12.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6520  -12.5712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9381  -11.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0523  -10.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3501  -11.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0452  -10.1174    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4721  -10.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  1  1  0
  1  2  2  0
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  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
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  4 10  1  0
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 12 18  1  0
 13 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  2 20  1  0
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 26 27  1  0
 26 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 33 35  1  0
 32 36  1  0
 36 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4577077

   ---

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: 568.42

Molecular Weight (Monoisotopic): 568.0383

AlogP: 3.81

#Rotatable Bonds: 8

Polar Surface Area: 191.20

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.88

CX Basic pKa: 4.10

CX LogP: 1.03

CX LogD: -1.48

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: -1.72

References

1. Lacbay CM, Waller DD, Park J, Gómez Palou M, Vincent F, Huang XF, Ta V, Berghuis AM, Sebag M, Tsantrizos YS..  (2018)  Unraveling the Prenylation-Cancer Paradox in Multiple Myeloma with Novel Geranylgeranyl Pyrophosphate Synthase (GGPPS) Inhibitors.,  61  (15): [PMID:30016091] [10.1021/acs.jmedchem.8b00886]

2. Lee HF, Lacbay CM, Boutin R, Matralis AN, Park J, Waller DD, Guan TL, Sebag M, Tsantrizos YS..  (2022)  Synthesis and Evaluation of Structurally Diverse C-2-Substituted Thienopyrimidine-Based Inhibitors of the Human Geranylgeranyl Pyrophosphate Synthase.,  65  (3.0): [PMID:35077178] [10.1021/acs.jmedchem.1c01913]

Source

Source(1):

• Scientific Literature