(1S,2S,3a1S,12bS)-1-hydroxy-2,3a1,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-2-yl benzoate

ID: ALA1922154

PubChem CID: 57402106

Max Phase: Preclinical

Molecular Formula: C23H21NO5

Molecular Weight: 391.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1C=C2CCN3Cc4cc5c(cc4[C@H]([C@@H]1O)[C@@H]23)OCO5)c1ccccc1

Standard InChI:  InChI=1S/C23H21NO5/c25-22-19(29-23(26)13-4-2-1-3-5-13)8-14-6-7-24-11-15-9-17-18(28-12-27-17)10-16(15)20(22)21(14)24/h1-5,8-10,19-22,25H,6-7,11-12H2/t19-,20-,21+,22+/m0/s1

Standard InChI Key:  PPRMAGAZSQCYCB-FNAHDJPLSA-N

Molfile:  

     RDKit          2D

 31 36  0  0  0  0  0  0  0  0999 V2000
   12.9623   -9.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9605   -7.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2506   -9.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2519   -8.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4674   -7.9469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9813   -8.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4654   -9.2821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6726   -8.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6760   -9.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3919   -9.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3852   -7.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8267   -6.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1065   -6.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3826   -6.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8229   -7.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1066   -8.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1113   -8.9349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9518   -9.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3680   -8.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1088   -5.7155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6715   -6.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0987   -7.3710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6677   -7.3668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8212   -5.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8234   -4.4854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5313   -5.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5247   -6.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2340   -6.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9474   -6.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9470   -5.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2371   -5.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
 15 16  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  8  9  1  0
  3  4  2  0
 17 18  1  0
 18 19  1  0
 15 19  1  0
  3  1  1  0
 13 20  1  1
  1  9  2  0
 14 21  1  6
 11  8  1  0
 16 22  1  6
  9 10  1  0
 11 23  1  1
 10 17  1  0
 20 24  1  0
 16 17  1  0
 24 25  2  0
 11 16  1  0
 24 26  1  0
 26 27  2  0
  8  2  2  0
 27 28  1  0
  2  4  1  0
 28 29  2  0
  4  5  1  0
 29 30  1  0
 11 14  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1922154

   [(1S,17S,18S,19S)-18-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-17-yl] benzoate

Molecule Features

Natural Product: No

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: 391.42

Molecular Weight (Monoisotopic): 391.1420

AlogP: 2.61

#Rotatable Bonds: 2

Polar Surface Area: 68.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.70

CX Basic pKa: 8.07

CX LogP: 2.66

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: 1.74

References

1. Evdokimov NM, Lamoral-Theys D, Mathieu V, Andolfi A, Frolova LV, Pelly SC, van Otterlo WA, Magedov IV, Kiss R, Evidente A, Kornienko A..  (2011)  In search of a cytostatic agent derived from the alkaloid lycorine: synthesis and growth inhibitory properties of lycorine derivatives.,  19  (23): [PMID:22019045] [10.1016/j.bmc.2011.09.051]

2. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature