(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S,Z)-3,11-dihydroxy-4,8,10,14-tetramethyl-17-(5-methyl-1-(3-propyl-1,2,4-oxadiazol-5-yl)hex-4-en-1-ylidene)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl acetate

ID: ALA3774517

PubChem CID: 122387676

Max Phase: Preclinical

Molecular Formula: C35H54N2O5

Molecular Weight: 582.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1noc(/C(CCC=C(C)C)=C2\[C@@H](OC(C)=O)C[C@@]3(C)[C@H]2C[C@@H](O)[C@H]2[C@@]4(C)CC[C@@H](O)[C@@H](C)[C@@H]4CC[C@@]23C)n1

Standard InChI:  InChI=1S/C35H54N2O5/c1-9-11-29-36-32(42-37-29)23(13-10-12-20(2)3)30-25-18-27(40)31-33(6)16-15-26(39)21(4)24(33)14-17-34(31,7)35(25,8)19-28(30)41-22(5)38/h12,21,24-28,31,39-40H,9-11,13-19H2,1-8H3/b30-23-/t21-,24-,25-,26+,27+,28-,31-,33-,34-,35-/m0/s1

Standard InChI Key:  TUEZINJKECMGNW-PFEUUVLWSA-N

Molfile:  

     RDKit          2D

 45 49  0  0  0  0  0  0  0  0999 V2000
    7.2492    0.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -0.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5279   -0.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2460    1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5036    2.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    0.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5310   -1.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7645    1.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4991    4.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677    0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458    1.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0034    2.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0312   -1.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7962    4.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -2.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    0.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7919   -2.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0619    2.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3648    1.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -1.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4019    2.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8920    8.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    7.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5565   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0533   -0.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    2.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1984    4.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1956    6.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -2.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2788   -3.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3694    0.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297    9.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8515    9.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7743   -0.6698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    2.7956    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386   -2.8260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1499    4.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1497    5.3046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3952    6.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9291    6.2841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9970    7.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1089    9.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5909   10.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  1  1  0
  5  4  1  0
  6  2  1  0
  7 17  1  0
  8 10  1  0
  9  5  2  0
 10  1  1  0
 11 12  1  0
 12  4  1  0
 13  2  1  0
 14  9  1  0
 15  7  1  0
 16  3  1  0
 17 13  1  0
  8 18  1  1
 19 18  1  0
 20 15  1  0
 21 16  1  0
 22 19  2  0
 23 24  2  0
 24 30  1  0
  1 25  1  1
  2 26  1  6
  3 27  1  1
 11 28  1  6
 29  9  1  0
 30 29  1  0
 20 31  1  6
 15 32  1  6
 33 19  1  0
 34 23  1  0
 35 23  1  0
  6 36  1  1
  4 37  1  6
  7 38  1  6
  8  5  1  0
 11  6  1  0
  3  7  1  0
 20 21  1  0
 14 39  1  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 14  2  0
 41 43  1  0
 43 44  1  0
 44 45  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3774517

   ---

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: 582.83

Molecular Weight (Monoisotopic): 582.4033

AlogP: 7.07

#Rotatable Bonds: 7

Polar Surface Area: 105.68

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.57

CX LogD: 6.57

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.26

Np Likeness Score: 1.96

References

1. Kaur G, Singh K, Pavadai E, Njoroge M, Espinoza-Moraga M, De Kock C, Smith PJ, Wittlin S, Chibale K.  (2015)  Synthesis of fusidic acid bioisosteres as antiplasmodial agents and molecular docking studies in the binding site of elongation factor-G,  6  (11): [10.1039/C5MD00343A]

2. Singh K,Kaur G,Shanika PS,Dziwornu GA,Okombo J,Chibale K.  (2020)  Structure-activity relationship analyses of fusidic acid derivatives highlight crucial role of the C-21 carboxylic acid moiety to its anti-mycobacterial activity.,  28  (13): [PMID:32362386] [10.1016/j.bmc.2020.115530]

Source

Source(1):

• Scientific Literature