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

ID: ALA1090223

PubChem CID: 46205774

Max Phase: Preclinical

Molecular Formula: C24H27ClNO6P

Molecular Weight: 491.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CO)(CCc1ccc(-c2ccc(OCc3ccccc3)cc2)cc1Cl)COP(=O)(O)O

Standard InChI:  InChI=1S/C24H27ClNO6P/c25-23-14-21(7-6-20(23)12-13-24(26,16-27)17-32-33(28,29)30)19-8-10-22(11-9-19)31-15-18-4-2-1-3-5-18/h1-11,14,27H,12-13,15-17,26H2,(H2,28,29,30)

Standard InChI Key:  GBCJASGKMQEDNP-UHFFFAOYSA-N

Molfile:  

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   -2.6761  -21.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3958  -24.3750    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:

   

   ALA1090223

   [2-Amino-4-[2-chloro-4-(4-phenylmethoxyphenyl)phenyl]-2-(hydroxymethyl)butyl] dihydrogen phosphate

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: 491.91

Molecular Weight (Monoisotopic): 491.1265

AlogP: 4.32

#Rotatable Bonds: 11

Polar Surface Area: 122.24

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.62

CX Basic pKa: 9.84

CX LogP: 3.12

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: 0.09

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