2-(4-((S)-3-(((R)-1-(naphthalen-1-yl)ethyl)amino)pyrrolidin-1-yl)benzamido)ethanesulfonic acid

ID: ALA4092377

PubChem CID: 137656029

Max Phase: Preclinical

Molecular Formula: C25H29N3O4S

Molecular Weight: 467.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](N[C@H]1CCN(c2ccc(C(=O)NCCS(=O)(=O)O)cc2)C1)c1cccc2ccccc12

Standard InChI:  InChI=1S/C25H29N3O4S/c1-18(23-8-4-6-19-5-2-3-7-24(19)23)27-21-13-15-28(17-21)22-11-9-20(10-12-22)25(29)26-14-16-33(30,31)32/h2-12,18,21,27H,13-17H2,1H3,(H,26,29)(H,30,31,32)/t18-,21+/m1/s1

Standard InChI Key:  ATKRVTITMZGBBL-NQIIRXRSSA-N

Molfile:  

     RDKit          2D

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   16.3727   -9.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6670   -9.0551    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6660   -9.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9559   -6.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1717   -5.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5854   -5.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8768   -4.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5883   -6.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8778   -6.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8762   -7.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3001   -5.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5010   -5.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5225   -5.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8516   -6.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6636   -6.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1440   -6.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8065   -5.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954   -5.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2912   -6.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8126   -7.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4334   -5.5731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1470   -8.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8554   -8.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  6  2  0
  6 10  1  0
  9  7  1  0
  7  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  9  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  1
 18 16  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26  4  1  0
  4 29  1  0
 29 30  1  0
  4 31  2  0
 30 32  1  0
 32  2  1  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092377

   ---

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: 467.59

Molecular Weight (Monoisotopic): 467.1879

AlogP: 3.39

#Rotatable Bonds: 8

Polar Surface Area: 98.74

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.10

CX Basic pKa: 9.46

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: -1.07

References

1. Sparks SM, Spearing PK, Diaz CJ, Cowan DJ, Jayawickreme C, Chen G, Rimele TJ, Generaux C, Harston LT, Roller SG..  (2017)  Identification of potent, nonabsorbable agonists of the calcium-sensing receptor for GI-specific administration.,  27  (20): [PMID:28916340] [10.1016/j.bmcl.2017.09.008]

Source

Source(1):

• Scientific Literature