(S)-4-(1H-indol-3-yl)-3-((R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-(isopropylcarbamoyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)butanoic acid

ID: ALA4776886

PubChem CID: 162643250

Max Phase: Preclinical

Molecular Formula: C40H59N3O5

Molecular Weight: 661.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)NC(=O)O[C@@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(=O)N[C@H](CC(=O)O)Cc4c[nH]c5ccccc45)CC[C@@H]32)C1

Standard InChI:  InChI=1S/C40H59N3O5/c1-24(2)42-38(47)48-29-16-18-39(4)27(21-29)11-12-31-33-14-13-32(40(33,5)19-17-34(31)39)25(3)10-15-36(44)43-28(22-37(45)46)20-26-23-41-35-9-7-6-8-30(26)35/h6-9,23-25,27-29,31-34,41H,10-22H2,1-5H3,(H,42,47)(H,43,44)(H,45,46)/t25-,27-,28+,29-,31+,32-,33+,34+,39+,40-/m1/s1

Standard InChI Key:  GGJMOJQQOWJUIM-WZYCFLAOSA-N

Molfile:  

 
     RDKit          2D

 53 58  0  0  0  0  0  0  0  0999 V2000
   29.0970  -19.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0970  -20.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8022  -21.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8022  -19.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5075  -19.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5040  -20.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2061  -21.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9161  -20.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2131  -19.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9196  -19.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9365  -18.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2184  -18.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6431  -18.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6298  -19.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4043  -19.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8964  -19.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4258  -18.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6216  -20.2771    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.2060  -20.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.5002  -19.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4961  -21.4822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.9117  -19.0430    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.6381  -17.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6910  -17.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4929  -17.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1541  -17.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0298  -18.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8318  -17.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3687  -18.5469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0969  -17.1578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2395  -18.3992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.3898  -21.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1707  -18.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7075  -19.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4358  -17.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2378  -17.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5029  -16.6871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7746  -18.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4424  -19.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6606  -20.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6474  -20.8331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9113  -20.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4203  -21.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7389  -21.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5482  -21.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0379  -21.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7166  -20.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6815  -20.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9744  -21.0808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6804  -19.8540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2661  -20.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5590  -21.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2649  -19.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 14 18  1  6
  9 19  1  6
  5 20  1  1
  6 21  1  1
 10 22  1  1
 13 23  1  1
 17 24  1  0
 24 25  1  0
 24 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 17 31  1  6
  2 32  1  6
 29 33  1  0
 33 34  1  6
 33 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 34 39  1  0
 39 40  2  0
 40 41  1  0
 41 43  1  0
 42 39  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 42  1  0
 32 48  1  0
 48 49  1  0
 48 50  2  0
 49 51  1  0
 51 52  1  0
 51 53  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776886

   ---

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: 661.93

Molecular Weight (Monoisotopic): 661.4455

AlogP: 8.25

#Rotatable Bonds: 11

Polar Surface Area: 120.52

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.57

CX Basic pKa: ┄

CX LogP: 7.43

CX LogD: 4.68

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.19

Np Likeness Score: 1.04

References

1. Incerti M,Russo S,Corrado M,Giorgio C,Ballabeni V,Chiodelli P,Rusnati M,Scalvini L,Callegari D,Castelli R,Vacondio F,Ferlenghi F,Tognolini M,Lodola A.  (2020)  Optimization of EphA2 antagonists based on a lithocholic acid core led to the identification of UniPR505, a new 3α-carbamoyloxy derivative with antiangiogenetic properties.,  189  [PMID:32000051] [10.1016/j.ejmech.2020.112083]

Source

Source(1):

• Scientific Literature