4-(((((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)carbonyl)amino)piperidin-1-ium chloride

ID: ALA5270787

Max Phase: Preclinical

Molecular Formula: C30H45ClN2O5

Molecular Weight: 512.69

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H](OC(=O)NC3CCNCC3)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O.Cl

Standard InChI:  InChI=1S/C30H44N2O5.ClH/c1-28-12-7-22(37-27(34)32-21-10-15-31-16-11-21)17-20(28)4-5-25-24(28)8-13-29(2)23(9-14-30(25,29)35)19-3-6-26(33)36-18-19;/h3,6,18,20-25,31,35H,4-5,7-17H2,1-2H3,(H,32,34);1H/t20-,22+,23-,24+,25-,28+,29-,30+;/m1./s1

Standard InChI Key:  KLDNGJAIPPKAKN-GSFHTSSDSA-N

Molfile:  

     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
   -5.6584   -0.9821    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5592   -2.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448   -2.7203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -2.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -1.4830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4158   -2.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -1.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279   -0.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -1.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    0.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -1.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -0.6589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -2.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -2.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279   -3.1335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -1.8962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6688   -1.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6688    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9162    0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665    1.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6139    2.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109    2.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6858    3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131    0.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -1.8967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737   -2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9881   -2.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2732   -1.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589   -1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9878   -1.4821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  4  5  2  0
  6  4  1  0
  7  6  1  1
  8  7  1  0
  9  8  1  0
 10  9  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 18 17  1  0
 18 12  1  0
 18 19  1  1
 18 20  1  0
 21 20  1  0
 22 21  1  0
 10 22  1  0
 22 23  1  0
  7 23  1  0
 22 24  1  1
 17 25  1  1
 17 26  1  0
 26 27  1  0
 27 28  1  0
 15 28  1  0
 28 29  1  1
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  2  0
 29 35  1  0
 12 36  1  6
 37  2  1  0
 38 37  1  0
 40 39  1  0
  2 40  1  0
 39 41  1  0
 38 41  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 512.69

Molecular Weight (Monoisotopic): 512.3250

AlogP: 4.73

#Rotatable Bonds: 3

Polar Surface Area: 100.80

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.03

CX LogP: 3.25

CX LogD: 0.72

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.54

Np Likeness Score: 1.84

References

1. Zhong Y, Zhao C, Wu WY, Fan TY, Li NG, Chen M, Duan JA, Shi ZH..  (2020)  Total synthesis, chemical modification and structure-activity relationship of bufadienolides.,  189  [PMID:31945667] [10.1016/j.ejmech.2020.112038]

Source

Source(1):

• Scientific Literature