(1R,2S,3S,4S,4aS,11bS)-1,3,4,7,11b-pentahydroxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl benzoate

ID: ALA4212108

PubChem CID: 10983140

Max Phase: Preclinical

Molecular Formula: C21H19NO10

Molecular Weight: 445.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@@H]2NC(=O)c3c(cc4c(c3O)OCO4)[C@@]2(O)[C@@H]1O)c1ccccc1

Standard InChI:  InChI=1S/C21H19NO10/c23-12-11-9(6-10-15(12)31-7-30-10)21(29)17(22-19(11)27)14(25)13(24)16(18(21)26)32-20(28)8-4-2-1-3-5-8/h1-6,13-14,16-18,23-26,29H,7H2,(H,22,27)/t13-,14+,16-,17-,18+,21-/m0/s1

Standard InChI Key:  ZHRSVGCLIJFPAW-RSBFFGIDSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    4.5193  -12.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136  -13.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193  -13.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292  -12.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136  -12.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292  -13.4094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037  -13.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5234  -11.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473  -12.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020  -13.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9597  -11.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020  -12.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037  -12.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2416  -10.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179  -13.6570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179  -12.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193  -14.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1350  -12.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037  -14.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6572  -12.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6737  -10.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -10.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292  -11.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094  -11.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172  -10.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5525   -9.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649   -8.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2795   -8.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2922   -7.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5903   -7.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740   -7.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648   -8.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387  -10.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6  4  1  0
  7  2  2  0
  8  1  1  0
  9  4  1  0
 10 12  2  0
 11 14  1  0
 12 13  1  0
 13  5  2  0
 14  8  1  0
 15 10  1  0
 16 12  1  0
 17  3  2  0
 18 16  1  0
 19  7  1  0
  9 20  1  1
 11 21  1  1
 14 22  1  1
  4 23  1  1
  3  6  1  0
 11  9  1  0
 10  7  1  0
 15 18  1  0
  1 24  1  6
  8 25  1  6
 22 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 26 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4212108

   [(1R,2S,3S,4S,4aS,11bS)-1,3,4,7,11b-pentahydroxy-6-oxo-1,2,3,4,4a,5-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-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: 445.38

Molecular Weight (Monoisotopic): 445.1009

AlogP: -1.26

#Rotatable Bonds: 2

Polar Surface Area: 175.01

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.39

CX Basic pKa: ┄

CX LogP: -0.08

CX LogD: -0.12

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: 1.81

References

1. Nair JJ, Wilhelm A, Bonnet SL, van Staden J..  (2017)  Antibacterial constituents of the plant family Amaryllidaceae.,  27  (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052]

Source

Source(1):

• Scientific Literature