(4S,5R,E)-5-(benzo[d][1,3]dioxol-5-yl)-4,5-dihydroxy-1-(piperidin-1-yl)pent-2-en-1-one

ID: ALA4859829

PubChem CID: 164610980

Max Phase: Preclinical

Molecular Formula: C17H21NO5

Molecular Weight: 319.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/[C@H](O)[C@H](O)c1ccc2c(c1)OCO2)N1CCCCC1

Standard InChI:  InChI=1S/C17H21NO5/c19-13(5-7-16(20)18-8-2-1-3-9-18)17(21)12-4-6-14-15(10-12)23-11-22-14/h4-7,10,13,17,19,21H,1-3,8-9,11H2/b7-5+/t13-,17+/m0/s1

Standard InChI Key:  OYFCOFKWCRBXAB-IGJNKPTASA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.4659  -13.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4659  -14.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1712  -14.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8765  -14.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8765  -13.2773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1712  -12.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5854  -12.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2919  -13.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0008  -12.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5878  -12.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7073  -13.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4162  -12.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1227  -13.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1151  -14.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8208  -14.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8242  -12.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5304  -13.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5271  -14.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3041  -14.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7877  -13.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3095  -13.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7049  -14.1028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4186  -12.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  7 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 18  2  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 11 22  1  1
 12 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4859829

   ---

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: 319.36

Molecular Weight (Monoisotopic): 319.1420

AlogP: 1.38

#Rotatable Bonds: 4

Polar Surface Area: 79.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.19

CX Basic pKa: ┄

CX LogP: 0.91

CX LogD: 0.91

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.82

Np Likeness Score: 0.50

References

1. Luo J, Xiang JY, Yuan HY, Wu JQ, Li HZ, Shen YH, Xu M..  (2021)  Isolation, synthesis and absolute configuration of 4,5-dihydroxypiperines improving behavioral disorder in AlCl₃-induced dementia.,  42  [PMID:33892105] [10.1016/j.bmcl.2021.128057]

Source

Source(1):

• Scientific Literature