6-(((4aR,6R,6aR,9S,11S,11aS,11bS,12R)-11b-(acetoxymethyl)-11-hydroxy-6-methoxy-4,4-dimethyl-8-methylene-7-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalen-12-yl)oxy)-(S)-6-oxohexane-1,5-diaminium-2,2,2-trifluoroacetate

ID: ALA4555385

PubChem CID: 155556942

Max Phase: Preclinical

Molecular Formula: C33H48F6N2O11

Molecular Weight: 534.69

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1C(=O)[C@]23[C@H](OC(=O)[C@@H](N)CCCCN)[C@H]1C[C@H](O)[C@H]2[C@]1(COC(C)=O)CCCC(C)(C)[C@H]1C[C@H]3OC.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C29H46N2O7.2C2HF3O2/c1-16-18-13-20(33)23-28(15-37-17(2)32)11-8-10-27(3,4)21(28)14-22(36-5)29(23,24(16)34)25(18)38-26(35)19(31)9-6-7-12-30;2*3-2(4,5)1(6)7/h18-23,25,33H,1,6-15,30-31H2,2-5H3;2*(H,6,7)/t18-,19-,20-,21+,22+,23-,25+,28-,29+;;/m0../s1

Standard InChI Key:  XRHIXHLKNKSALE-SABBIYPCSA-N

Molfile:  

     RDKit          2D

 55 56  0  0  0  0  0  0  0  0999 V2000
   33.3439  -16.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0516  -16.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7593  -16.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0516  -15.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6362  -16.4057    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.3439  -17.6315    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.6340  -17.2188    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.7338  -14.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3417  -14.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9410  -14.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6566  -12.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6566  -13.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3453  -12.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0341  -12.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0306  -13.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7121  -14.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4056  -13.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7190  -12.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4052  -12.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0925  -12.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1040  -11.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4178  -11.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7243  -11.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0227  -14.5774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.4053  -12.1877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.6682  -12.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1688  -13.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4628  -12.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2182  -10.9982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.4792  -13.9606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7994  -13.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0209  -11.3790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0268  -12.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3155  -11.7689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3082  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5968  -10.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0122  -10.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1113  -14.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1073  -15.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2006  -13.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0178  -13.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7885  -14.4369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4300  -13.0298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4228  -14.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2400  -14.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6450  -15.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4622  -15.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8672  -15.8730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0414  -11.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7491  -10.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4568  -11.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7491  -10.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3337  -10.8175    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.0414  -12.0433    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.3315  -11.6305    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  9  8  1  0
 10  9  1  0
 11 12  1  0
 11 13  1  0
 12  9  1  0
  9 15  1  0
 14 13  1  0
 14 15  1  0
 14 18  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 15 24  1  1
 18 25  1  1
 21 26  1  0
 19 27  1  1
 27 26  1  0
 26 28  2  0
 21 29  1  6
 27 30  2  0
 20 31  1  1
 23 32  1  1
 14 33  1  6
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 17 38  1  6
 38 39  1  0
 31 40  1  0
 40 41  1  0
 40 42  2  0
 41 43  1  0
 41 44  1  1
 44 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 49 50  1  0
 50 51  1  0
 50 52  2  0
 49 53  1  0
 49 54  1  0
 49 55  1  0
M  END

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: 534.69

Molecular Weight (Monoisotopic): 534.3305

AlogP: 2.27

#Rotatable Bonds: 9

Polar Surface Area: 151.17

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.21

CX LogP: 1.53

CX LogD: -1.29

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.23

Np Likeness Score: 2.93

References

1. Ke Y, Hu TX, Huo JF, Yan JK, Wang JY, Yang RH, Xie H, Liu Y, Wang N, Zheng ZJ, Sun YX, Wang C, Du J, Liu HM..  (2019)  Synthesis and in vitro biological evaluation of novel derivatives of Flexicaulin A condensation with amino acid trifluoroacetate.,  182  [PMID:31494472] [10.1016/j.ejmech.2019.111645]

Source

Source(1):

• Scientific Literature