(1S,2S,3a1S,12bS)-2,3a1,4,5,7,12b-Hexahydro-1H-[1,3]-dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diyl dibenzoate

ID: ALA1922153

PubChem CID: 57393385

Max Phase: Preclinical

Molecular Formula: C30H25NO6

Molecular Weight: 495.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1[C@H]2c3cc4c(cc3CN3CCC(=C[C@@H]1OC(=O)c1ccccc1)[C@H]23)OCO4)c1ccccc1

Standard InChI:  InChI=1S/C30H25NO6/c32-29(18-7-3-1-4-8-18)36-25-13-20-11-12-31-16-21-14-23-24(35-17-34-23)15-22(21)26(27(20)31)28(25)37-30(33)19-9-5-2-6-10-19/h1-10,13-15,25-28H,11-12,16-17H2/t25-,26-,27+,28+/m0/s1

Standard InChI Key:  HOLYIGNDGYEYLM-YVHASNINSA-N

Molfile:  

     RDKit          2D

 39 45  0  0  0  0  0  0  0  0999 V2000
   -2.7499   -9.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -8.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4637   -9.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -8.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -8.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366   -8.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2511   -9.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376   -8.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -9.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3162   -9.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229   -8.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1227   -7.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -6.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255   -7.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189   -8.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994   -8.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5634   -9.2725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482   -9.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6656   -8.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -6.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387   -6.8709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6073   -7.7041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -7.6999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -5.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194   -4.8103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384   -6.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -5.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249   -5.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -6.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7462   -4.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4585   -4.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729   -4.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1706   -5.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577   -6.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8228   -6.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5341   -7.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495   -6.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2491   -6.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5372   -5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 21 26  1  0
 26 27  1  0
  8  2  2  0
 26 28  2  0
  2  4  1  0
 24 29  1  0
  4  5  1  0
 27 30  2  0
 11 14  1  0
 30 31  1  0
 15 12  2  0
 31 32  2  0
 12 13  1  0
 32 33  1  0
 13 14  1  0
 33 34  2  0
 34 27  1  0
 15 16  1  0
 29 35  2  0
  5  6  1  0
 35 36  1  0
  6  7  1  0
 36 37  2  0
  7  3  1  0
 37 38  1  0
  8  9  1  0
 38 39  2  0
 39 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1922153

   [(1S,17S,18S,19S)-18-benzoyloxy-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: 495.53

Molecular Weight (Monoisotopic): 495.1682

AlogP: 4.48

#Rotatable Bonds: 4

Polar Surface Area: 74.30

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.23

CX LogP: 5.15

CX LogD: 4.26

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.39

Np Likeness Score: 1.32

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