2-((4S,5S,8S,9S,10S,11R,13R,14S,16S,E)-16-acetoxy-11-hydroxy-3-(hydroxyimino)-4,8,10,14-tetramethyldodecahydro-1H-cyclopenta[a]phenanthren-17(2H,10H,14H)-ylidene)-6-methylhept-5-enoic acid

ID: ALA4764527

PubChem CID: 162661689

Max Phase: Preclinical

Molecular Formula: C31H47NO6

Molecular Weight: 529.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C[C@@]2(C)[C@@H](C[C@@H](O)[C@H]3[C@@]4(C)CC/C(=N\O)[C@@H](C)[C@@H]4CC[C@@]32C)/C1=C(\CCC=C(C)C)C(=O)O

Standard InChI:  InChI=1S/C31H47NO6/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(32-37)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)38-19(4)33/h9,18,21-22,24-25,27,34,37H,8,10-16H2,1-7H3,(H,35,36)/b26-20-,32-23+/t18-,21-,22-,24+,25-,27-,29-,30-,31-/m0/s1

Standard InChI Key:  OLHYORJNFFXLGE-JUIPTJOVSA-N

Molfile:  

 
     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
   24.3779  -18.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6647  -18.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2382  -18.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3779  -17.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1658  -17.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9514  -18.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2382  -19.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6509  -17.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4146  -16.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1658  -18.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9514  -17.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6647  -17.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6647  -19.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2397  -16.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5250  -20.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5250  -18.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9514  -20.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4761  -17.9714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8907  -18.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8118  -19.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8118  -18.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4761  -19.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5922  -14.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2024  -15.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3282  -19.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6854  -17.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2631  -17.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2382  -17.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9916  -15.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3772  -15.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0986  -20.0322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5250  -20.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7159  -18.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1651  -13.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4256  -14.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9265  -19.2070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4649  -16.7316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.2092  -20.4469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.7117  -17.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7453  -15.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3881  -19.6208    0.0000 O   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  2  0
 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
  5  8  1  0
  6 11  1  0
  7  3  1  0
 21 20  1  0
 14 39  1  0
 40 14  2  0
 31 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764527

   ---

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: 529.72

Molecular Weight (Monoisotopic): 529.3403

AlogP: 6.14

#Rotatable Bonds: 5

Polar Surface Area: 116.42

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.46

CX Basic pKa: 2.44

CX LogP: 4.82

CX LogD: 1.97

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.13

Np Likeness Score: 2.76

References

1. 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