2-Amino-4-(4'-benzylthio-3-chlorobiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

ID: ALA1092285

Max Phase: Preclinical

Molecular Formula: C25H29ClNO4PS

Molecular Weight: 506.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=P(O)(O)OCC(N)(CO)CCc1ccc(-c2ccc(SCc3ccccc3)cc2)cc1Cl

Standard InChI:  InChI=1S/C25H29ClNO4PS/c1-32(29,30)31-18-25(27,17-28)14-13-21-7-8-22(15-24(21)26)20-9-11-23(12-10-20)33-16-19-5-3-2-4-6-19/h2-12,15,28-30H,1,13-14,16-18,27H2

Standard InChI Key:  WEYWOPITACEWLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.1031   -2.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2738   -2.4449    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1092285

   ---

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: 506.00

Molecular Weight (Monoisotopic): 505.1243

AlogP: 5.12

#Rotatable Bonds: 11

Polar Surface Area: 95.94

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.69

CX Basic pKa: 9.16

CX LogP: 3.90

CX LogD: 3.64

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.30

References

1. Hamada M, Nakamura M, Kiuchi M, Marukawa K, Tomatsu A, Shimano K, Sato N, Sugahara K, Asayama M, Takagi K, Adachi K..  (2010)  Removal of sphingosine 1-phosphate receptor-3 (S1P(3)) agonism is essential, but inadequate to obtain immunomodulating 2-aminopropane-1,3-diol S1P(1) agonists with reduced effect on heart rate.,  53  (8): [PMID:20337461] [10.1021/jm901776q]

Source

Source(1):

• Scientific Literature