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

ID: ALA4538679

PubChem CID: 135262739

Max Phase: Preclinical

Molecular Formula: C21H20N4O8P2S

Molecular Weight: 550.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)c2cccc(-c3nc(NC(P(=O)(O)O)P(=O)(O)O)c4ccsc4n3)c2)cc1

Standard InChI:  InChI=1S/C21H20N4O8P2S/c1-33-15-7-5-14(6-8-15)22-19(26)13-4-2-3-12(11-13)17-23-18(16-9-10-36-20(16)24-17)25-21(34(27,28)29)35(30,31)32/h2-11,21H,1H3,(H,22,26)(H,23,24,25)(H2,27,28,29)(H2,30,31,32)

Standard InChI Key:  AYOCHHJBZWKCSC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.3319   -5.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291   -4.4331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6204   -4.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1498   -4.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5693   -5.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 20  1  0
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 27 29  1  0
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 32 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538679

   ---

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: 550.43

Molecular Weight (Monoisotopic): 550.0477

AlogP: 3.67

#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: 0.88

CX LogD: -1.62

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.18

Np Likeness Score: -1.47

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