(2S,3R)-2-Amino-3-hydroxy-N-octadecylbutanamide

ID: ALA4530144

PubChem CID: 74223368

Max Phase: Preclinical

Molecular Formula: C22H46N2O2

Molecular Weight: 370.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCCNC(=O)[C@@H](N)[C@@H](C)O

Standard InChI:  InChI=1S/C22H46N2O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-22(26)21(23)20(2)25/h20-21,25H,3-19,23H2,1-2H3,(H,24,26)/t20-,21+/m1/s1

Standard InChI Key:  QKQQPSLGYFFXKK-RTWAWAEBSA-N

Molfile:  

 
     RDKit          2D

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   14.6310  -13.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4523  -13.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2183  -12.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2183  -14.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8651  -14.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8609  -12.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6864  -12.6480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4523  -11.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0950  -13.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9122  -13.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3208  -14.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1380  -14.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5466  -13.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3637  -13.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7723  -12.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5895  -12.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9981  -13.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5895  -14.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9981  -14.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5895  -15.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9981  -16.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5895  -16.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7723  -16.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3637  -17.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5466  -17.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1380  -18.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  1
  1  4  1  0
  2  5  1  1
  2  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
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 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4530144

   (2S,3R)-2-Amino-3-hydroxy-N-octadecylbutanamide

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: 370.62

Molecular Weight (Monoisotopic): 370.3559

AlogP: 5.07

#Rotatable Bonds: 19

Polar Surface Area: 75.35

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.92

CX LogP: 5.76

CX LogD: 5.12

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: 0.07

References

1. Liu Q, Li X, Bao YS, Lu J, Li H, Huang Z, Liu F..  (2019)  Chemical synthesis and functional characterization of a new class of ceramide analogues as anti-cancer agents.,  27  (8): [PMID:30837168] [10.1016/j.bmc.2019.02.030]

Source

Source(1):

• Scientific Literature