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

ID: ALA4746495

PubChem CID: 162648475

Max Phase: Preclinical

Molecular Formula: C37H53N3O5

Molecular Weight: 619.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](CCC(=O)N[C@H](CC(=O)O)Cc1c[nH]c2ccccc12)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](OC(N)=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C37H53N3O5/c1-22(8-13-33(41)40-25(20-34(42)43)18-23-21-39-32-7-5-4-6-27(23)32)29-11-12-30-28-10-9-24-19-26(45-35(38)44)14-16-36(24,2)31(28)15-17-37(29,30)3/h4-7,21-22,24-26,28-31,39H,8-20H2,1-3H3,(H2,38,44)(H,40,41)(H,42,43)/t22-,24-,25+,26+,28+,29-,30+,31+,36+,37-/m1/s1

Standard InChI Key:  FAAZTHVEPPRZQA-GJNKDAHUSA-N

Molfile:  

 
     RDKit          2D

 50 55  0  0  0  0  0  0  0  0999 V2000
    3.8259   -4.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -5.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5312   -5.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5312   -4.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2365   -4.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -5.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9351   -5.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6451   -5.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9420   -4.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6486   -4.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6655   -2.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474   -3.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3721   -3.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3588   -4.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1333   -4.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6253   -3.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1548   -3.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506   -4.9857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -4.9692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -3.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251   -6.1908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6407   -3.7517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3671   -2.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4199   -2.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2219   -2.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8831   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7588   -2.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5608   -2.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0977   -3.2555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8259   -1.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9685   -3.1078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188   -5.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8996   -3.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4365   -3.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1648   -2.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9667   -2.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2319   -1.3957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5036   -2.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1714   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3896   -4.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3763   -5.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6403   -5.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1493   -5.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4679   -6.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2771   -6.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7668   -5.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4456   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4105   -5.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -5.7895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093   -4.5626    0.0000 O   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  1
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4746495

   ---

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: 619.85

Molecular Weight (Monoisotopic): 619.3985

AlogP: 7.21

#Rotatable Bonds: 10

Polar Surface Area: 134.51

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.57

CX Basic pKa: ┄

CX LogP: 6.43

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.22

Np Likeness Score: 1.28

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