(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-((4aR,6aS,6bR,8aR,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-5,10-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxamido)-4-(prop-1-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl diacetate

ID: ALA5183759

PubChem CID: 168280558

Max Phase: Preclinical

Molecular Formula: C45H65NO11

Molecular Weight: 796.01

Names and Identifiers

Canonical SMILES:  C=C(C)O[C@@H]1[C@@H](OC(C)=O)[C@H](NC(=O)[C@]23CCC(C)(C)C[C@H]2C2=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]2(C)CC3=O)O[C@H](COC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C45H65NO11/c1-24(2)54-36-35(55-26(4)48)30(23-53-25(3)47)57-38(37(36)56-27(5)49)46-39(52)45-20-19-40(6,7)21-29(45)28-13-14-32-42(10)17-16-33(50)41(8,9)31(42)15-18-43(32,11)44(28,12)22-34(45)51/h13,29-32,35-38H,1,14-23H2,2-12H3,(H,46,52)/t29-,30+,31-,32+,35-,36-,37+,38+,42-,43+,44+,45+/m0/s1

Standard InChI Key:  VSCZSYJYXJHWTK-NNZSHRABSA-N

Molfile:  

 
     RDKit          2D

 60 65  0  0  0  0  0  0  0  0999 V2000
   -8.7806    3.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0524    3.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3525    3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1092    2.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8090    2.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5373    2.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5657    1.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8658    1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1375    1.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2940    1.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9937    1.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9654    2.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2371    2.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7089    1.1327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7082    0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8821    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5363    3.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1081    3.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6810    2.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9528    2.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9244    3.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6242    3.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5959    4.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8676    5.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677    4.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    3.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4534    5.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2786    5.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1351    3.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5319    3.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9491    2.3886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    2.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5564    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    2.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5811    1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1844    1.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737    1.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -0.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4155   -1.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0188   -1.6313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6262   -1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    1.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6057    0.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8164    0.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1639    3.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745    2.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713    3.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885    1.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425    3.5149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393    4.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253    4.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500    3.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2528    2.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3819    1.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8374    1.8825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5941    0.6704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6527    3.0456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 10  1  0
  8 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  7 14  1  0
 12 15  2  0
 11 16  1  0
 11 17  1  0
  7 18  1  1
  5 19  1  1
  4 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  3 23  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 22 27  1  0
 25 28  1  0
 25 29  1  0
 22 30  1  1
 30 31  2  0
 30 32  1  0
 33 32  1  1
 34 33  1  0
 35 34  1  0
 36 35  1  0
 37 36  1  0
 38 37  1  0
 33 38  1  0
 37 39  1  1
 39 40  1  0
 40 41  1  0
 41 42  2  0
 41 43  1  0
 36 44  1  1
 44 45  1  0
 45 46  1  0
 45 47  2  0
 35 48  1  1
 48 49  1  0
 49 50  1  0
 49 51  2  0
 34 52  1  6
 52 53  1  0
 53 54  2  0
 53 55  1  0
 21 56  2  0
  4 57  1  6
  6 58  1  6
  8 59  1  6
 23 60  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5183759

   ---

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: 796.01

Molecular Weight (Monoisotopic): 795.4558

AlogP: 6.72

#Rotatable Bonds: 8

Polar Surface Area: 160.60

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.79

CX Basic pKa: ┄

CX LogP: 6.04

CX LogD: 6.04

Aromatic Rings: ┄

Heavy Atoms: 57

QED Weighted: 0.09

Np Likeness Score: 2.31

References

1. Christy MP, Uekusa Y, Gerwick L, Gerwick WH..  (2021)  Natural Products with Potential to Treat RNA Virus Pathogens Including SARS-CoV-2.,  84  (1.0): [PMID:33352046] [10.1021/acs.jnatprod.0c00968]

Source

Source(1):

• Scientific Literature