(+/-)-8,9-diethoxy-2,3,4,7-tetrahydroxy-1,3,4,4a,5,10bhexahydrophenanthridin-6(2H)-one

ID: ALA4514214

PubChem CID: 155539197

Max Phase: Preclinical

Molecular Formula: C17H23NO7

Molecular Weight: 353.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1cc2c(c(O)c1OCC)C(=O)NC1C2CC(O)C(O)C1O

Standard InChI:  InChI=1S/C17H23NO7/c1-3-24-10-6-7-8-5-9(19)13(20)15(22)12(8)18-17(23)11(7)14(21)16(10)25-4-2/h6,8-9,12-13,15,19-22H,3-5H2,1-2H3,(H,18,23)

Standard InChI Key:  GXZHPPBBCPUHBT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   24.3775  -16.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0861  -16.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0849  -17.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7911  -17.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5030  -17.2660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7934  -16.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5000  -16.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2090  -16.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2176  -15.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5110  -14.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7959  -15.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7889  -18.4903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5182  -13.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9290  -14.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9129  -16.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6679  -16.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9605  -16.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2525  -16.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3793  -17.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6667  -17.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9584  -17.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3835  -18.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2506  -17.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5430  -17.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5451  -16.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19  3  2  0
  2  1  2  0
  1 16  1  0
  2  3  1  0
  2  6  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  4 12  2  0
 10 13  1  0
  9 14  1  0
  8 15  1  0
 20 16  2  0
 16 17  1  0
 17 18  1  0
 19 20  1  0
 19 22  1  0
 20 21  1  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514214

   ---

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: 353.37

Molecular Weight (Monoisotopic): 353.1475

AlogP: -0.13

#Rotatable Bonds: 4

Polar Surface Area: 128.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.63

CX Basic pKa: ┄

CX LogP: -0.11

CX LogD: -0.13

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: 1.52

References

1. Varró G, Pálchuber P, Pogrányi B, Simon A, Hegedűs L, Kádas I..  (2019)  (±)-trans-Dihydronarciclasine and (±)-trans-dihydrolycoricidine analogues modified in their ring A: Evaluation of their anticancer activity and a SAR study.,  173  [PMID:30986573] [10.1016/j.ejmech.2019.04.010]

Source

Source(1):

• Scientific Literature