(3S)-3-(4-Aminobutyl)-4-hydroxy-1-[2-(6-methoxypyridin-3-yl)benzyl]-4-oxo-1,4-azaphosphinane-3-carboxylic Acid

ID: ALA4858095

PubChem CID: 135365123

Max Phase: Preclinical

Molecular Formula: C22H30N3O5P

Molecular Weight: 447.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccccc2CN2CCP(=O)(O)[C@](CCCCN)(C(=O)O)C2)cn1

Standard InChI:  InChI=1S/C22H30N3O5P/c1-30-20-9-8-17(14-24-20)19-7-3-2-6-18(19)15-25-12-13-31(28,29)22(16-25,21(26)27)10-4-5-11-23/h2-3,6-9,14H,4-5,10-13,15-16,23H2,1H3,(H,26,27)(H,28,29)/t22-/m0/s1

Standard InChI Key:  AVHRAGMQIMFUSI-QFIPXVFZSA-N

Molfile:  

 
     RDKit          2D

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    5.9845  -11.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5759  -12.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4012  -12.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520  -12.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8655  -13.6611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8655  -14.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1587  -15.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8646  -16.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8652  -16.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731  -17.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2808  -16.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2762  -16.0977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5677  -15.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9901  -17.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6962  -16.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 17  1  0
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 18 19  2  0
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 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 23 24  1  0
 27 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4858095

   ---

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: 447.47

Molecular Weight (Monoisotopic): 447.1923

AlogP: 2.80

#Rotatable Bonds: 9

Polar Surface Area: 125.98

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.60

CX Basic pKa: 10.52

CX LogP: -5.06

CX LogD: -4.98

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.40

References

1. Schaffner AP, Sansilvestri-Morel P, Despaux N, Ruano E, Persigand T, Rupin A, Mennecier P, Vallez MO, Raimbaud E, Desos P, Gloanec P..  (2021)  Phosphinanes and Azaphosphinanes as Potent and Selective Inhibitors of Activated Thrombin-Activatable Fibrinolysis Inhibitor (TAFIa).,  64  (7.0): [PMID:33764059] [10.1021/acs.jmedchem.0c02072]

Source

Source(1):

• Scientific Literature