2-Amino-4-(3-chloro-4'-phenoxybiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

ID: ALA1093574

PubChem CID: 46205455

Max Phase: Preclinical

Molecular Formula: C23H25ClNO6P

Molecular Weight: 477.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CO)(CCc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1Cl)COP(=O)(O)O

Standard InChI:  InChI=1S/C23H25ClNO6P/c24-22-14-19(17-8-10-21(11-9-17)31-20-4-2-1-3-5-20)7-6-18(22)12-13-23(25,15-26)16-30-32(27,28)29/h1-11,14,26H,12-13,15-16,25H2,(H2,27,28,29)

Standard InChI Key:  DZBUZOQYHZEZEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.5819  -18.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5819  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4069  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2964  -18.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8194  -20.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7569  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3444  -18.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8694  -18.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2819  -17.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1069  -17.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5194  -18.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1069  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2819  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0444  -18.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6319  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8069  -19.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3944  -18.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8069  -17.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6319  -17.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5694  -18.7020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1569  -17.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3319  -17.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9194  -17.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3319  -16.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1569  -16.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5694  -17.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5194  -17.2730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.5819  -20.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2917  -17.3458    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.2875  -16.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4583  -17.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1250  -17.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  6  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
  8 14  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
 17 20  1  0
 10 27  1  0
  7 11  1  0
  2  6  1  0
  2 28  1  0
  4 29  1  0
  1  2  1  0
 29 30  2  0
  2  3  1  0
 29 31  1  0
  1  4  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093574

   2-Amino-4-(3-chloro-4''-phenoxybiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

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: 477.88

Molecular Weight (Monoisotopic): 477.1108

AlogP: 4.53

#Rotatable Bonds: 10

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: 3.05

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.16

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