(S)-(3-Phenyl-2-((6-(p-tolyl)thieno[2,3-d]pyrimidin-4-yl)-amino)propanoyl)phosphoramidic Acid

ID: ALA4094213

PubChem CID: 124220689

Max Phase: Preclinical

Molecular Formula: C22H21N4O4PS

Molecular Weight: 468.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2cc3c(N[C@@H](Cc4ccccc4)C(=O)NP(=O)(O)O)ncnc3s2)cc1

Standard InChI:  InChI=1S/C22H21N4O4PS/c1-14-7-9-16(10-8-14)19-12-17-20(23-13-24-22(17)32-19)25-18(21(27)26-31(28,29)30)11-15-5-3-2-4-6-15/h2-10,12-13,18H,11H2,1H3,(H,23,24,25)(H3,26,27,28,29,30)/t18-/m0/s1

Standard InChI Key:  FWELKNKHGIBMRD-SFHVURJKSA-N

Molfile:  

     RDKit          2D

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   34.9164  -18.2011    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   35.7334  -18.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8496  -19.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.9112  -20.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.4969  -18.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2015  -17.8051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5098  -19.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8052  -19.4646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8181  -20.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1135  -20.7049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3960  -20.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6200  -20.5695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.9331  -19.0201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
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 14 15  1  0
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 29 30  2  0
 13 30  1  0
 30 31  1  0
 11 31  1  0
  2 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094213

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 468.48

Molecular Weight (Monoisotopic): 468.1021

AlogP: 3.90

#Rotatable Bonds: 7

Polar Surface Area: 124.44

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.91

CX Basic pKa: 3.83

CX LogP: 1.92

CX LogD: -0.75

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -0.86

References

1. Park J, Leung CY, Matralis AN, Lacbay CM, Tsakos M, Fernandez De Troconiz G, Berghuis AM, Tsantrizos YS..  (2017)  Pharmacophore Mapping of Thienopyrimidine-Based Monophosphonate (ThP-MP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase.,  60  (5): [PMID:28208018] [10.1021/acs.jmedchem.6b01888]

Source

Source(1):

• Scientific Literature