SID50110086

ID: ALA1596034

PubChem CID: 16398230

Max Phase: Preclinical

Molecular Formula: C18H27NO6

Molecular Weight: 353.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)cc1

Standard InChI:  InChI=1S/C18H27NO6/c1-4-10(2)12-5-7-13(8-6-12)24-18-15(19-11(3)21)17(23)16(22)14(9-20)25-18/h5-8,10,14-18,20,22-23H,4,9H2,1-3H3,(H,19,21)/t10?,14-,15-,16-,17-,18-/m1/s1

Standard InChI Key:  NZLBBWKRFWAHOK-NTCFCCFRSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
    4.4459   -0.8540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604   -2.0915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025   -2.0915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025   -0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -4.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -2.9165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -2.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -1.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -1.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604   -2.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -3.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -3.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -3.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604   -4.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -4.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -4.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604   -5.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025   -2.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -5.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -5.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -6.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0
  1 12  1  0
  9  2  1  1
  2 13  1  0
 10  3  1  1
 11  4  1  6
  5 14  1  0
  6 15  2  0
  8  7  1  6
  7 15  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 14  1  1
 13 16  2  0
 13 17  1  0
 15 22  1  0
 16 19  1  0
 17 20  2  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 23  1  0
 21 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1596034

   4-(butan-2-yl)phenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside

Molecule Features

Natural Product: Yes

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: 353.42

Molecular Weight (Monoisotopic): 353.1838

AlogP: 0.52

#Rotatable Bonds: 6

Polar Surface Area: 108.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: ┄

CX LogP: 0.80

CX LogD: 0.80

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 0.85

References

1. PubChem BioAssay data set, 

2. Liu Q,Miao Y,Wang X,Lv G,Peng Y,Li K,Li M,Qiu L,Lin J.  (2020)  Structure-based virtual screening and biological evaluation of novel non-bisphosphonate farnesyl pyrophosphate synthase inhibitors.,  186  [PMID:31785819] [10.1016/j.ejmech.2019.111905]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays