(+/-)-7,8-diethoxy-2,3,4-trihydroxy-9-methoxy-1,3,4,4a,5,10b-hexahydrophenanthridin-6(2H)-one

ID: ALA4474934

PubChem CID: 155537528

Max Phase: Preclinical

Molecular Formula: C18H25NO7

Molecular Weight: 367.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1c(OC)cc2c(c1OCC)C(=O)NC1C2CC(O)C(O)C1O

Standard InChI:  InChI=1S/C18H25NO7/c1-4-25-16-11(24-3)7-8-9-6-10(20)14(21)15(22)13(9)19-18(23)12(8)17(16)26-5-2/h7,9-10,13-15,20-22H,4-6H2,1-3H3,(H,19,23)

Standard InChI Key:  PJLWGUSLESAWJV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   24.2165   -8.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9251   -9.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9240   -9.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6302  -10.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3421   -9.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6325   -8.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3391   -9.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0480   -8.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0566   -7.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3501   -7.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6349   -7.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6279  -11.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3572   -6.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7681   -7.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7520   -9.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5069   -9.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7996   -8.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0915   -9.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2183  -10.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5058   -9.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7975  -10.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2225  -11.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0896   -9.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5170  -11.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3821  -10.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5212  -12.4200    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
 22 24  1  0
 23 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474934

   ---

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: 367.40

Molecular Weight (Monoisotopic): 367.1631

AlogP: 0.17

#Rotatable Bonds: 5

Polar Surface Area: 117.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.91

CX Basic pKa: ┄

CX LogP: -0.61

CX LogD: -0.61

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: 1.47

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