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

ID: ALA3735125

Cas Number: 1639159-47-9

PubChem CID: 91668293

Max Phase: Preclinical

Molecular Formula: C36H52N2O4

Molecular Weight: 576.82

Molecule Type: Small molecule

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](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C36H52N2O4/c1-22(8-13-33(40)38-25(20-34(41)42)18-23-21-37-32-7-5-4-6-27(23)32)29-11-12-30-28-10-9-24-19-26(39)14-16-35(24,2)31(28)15-17-36(29,30)3/h4-7,21-22,24-26,28-31,37,39H,8-20H2,1-3H3,(H,38,40)(H,41,42)/t22-,24-,25+,26-,28+,29-,30+,31+,35+,36-/m1/s1

Standard InChI Key:  JGYYGEYIQBZUCC-ZOOAIUBFSA-N

Molfile:  

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  7 47  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3735125

   UniPR129

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: 576.82

Molecular Weight (Monoisotopic): 576.3927

AlogP: 7.11

#Rotatable Bonds: 9

Polar Surface Area: 102.42

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.57

CX Basic pKa: ┄

CX LogP: 6.33

CX LogD: 3.58

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.26

Np Likeness Score: 1.34

References

1. Castelli R, Tognolini M, Vacondio F, Incerti M, Pala D, Callegari D, Bertoni S, Giorgio C, Hassan-Mohamed I, Zanotti I, Bugatti A, Rusnati M, Festuccia C, Rivara S, Barocelli E, Mor M, Lodola A..  (2015)  Δ(5)-Cholenoyl-amino acids as selective and orally available antagonists of the Eph-ephrin system.,  103  [PMID:26363867] [10.1016/j.ejmech.2015.08.048]

2. Incerti M, Russo S, Callegari D, Pala D, Giorgio C, Zanotti I, Barocelli E, Vicini P, Vacondio F, Rivara S, Castelli R, Tognolini M, Lodola A..  (2017)  Metadynamics for Perspective Drug Design: Computationally Driven Synthesis of New Protein-Protein Interaction Inhibitors Targeting the EphA2 Receptor.,  60  (2): [PMID:28005388] [10.1021/acs.jmedchem.6b01642]

3. Lodola A, Giorgio C, Incerti M, Zanotti I, Tognolini M..  (2017)  Targeting Eph/ephrin system in cancer therapy.,  142  [PMID:28780190] [10.1016/j.ejmech.2017.07.029]

4. 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