(S)-3-(3-(4-guanidinobutyl)ureido)-2-((S)-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)propanoic acid

ID: ALA4764427

PubChem CID: 131965316

Max Phase: Preclinical

Molecular Formula: C20H31N7O6S

Molecular Weight: 497.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)NCCCCNC(=O)NC[C@H](NC(=O)[C@@H]1CCCN1S(=O)(=O)c1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C20H31N7O6S/c21-19(22)23-10-4-5-11-24-20(31)25-13-15(18(29)30)26-17(28)16-9-6-12-27(16)34(32,33)14-7-2-1-3-8-14/h1-3,7-8,15-16H,4-6,9-13H2,(H,26,28)(H,29,30)(H4,21,22,23)(H2,24,25,31)/t15-,16-/m0/s1

Standard InChI Key:  IUFCIFVCEOUHLU-HOTGVXAUSA-N

Molfile:  

 
     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   35.6056   -2.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3910   -3.2027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.1866   -2.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5880   -4.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3024   -3.9187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   43.4477   -4.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1621   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5890   -5.1554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8756   -3.9222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.1643   -4.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.7406   -4.3376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4509   -3.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.0273   -3.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5708   -4.0060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0206   -4.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4301   -5.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2333   -5.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6130   -2.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4478   -2.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6706   -1.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0658   -2.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2393   -3.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0162   -3.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8744   -4.3199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.5858   -3.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2981   -4.3181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.5847   -3.0850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  2  0
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 15 16  2  0
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 19 18  1  6
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 21  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  9 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764427

   ---

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: 497.58

Molecular Weight (Monoisotopic): 497.2057

AlogP: -1.03

#Rotatable Bonds: 12

Polar Surface Area: 206.81

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.27

CX Basic pKa: 12.04

CX LogP: -3.06

CX LogD: -3.06

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.11

Np Likeness Score: -1.03

References

1. Sundaram A,Chen C,Isik Reed N,Liu S,Ki Yeon S,McIntosh J,Tang YZ,Yang H,Adler M,Beresis R,Seiple IB,Sheppard D,DeGrado WF,Jo H.  (2020)  Dual antagonists of α5β1/αvβ1 integrin for airway hyperresponsiveness.,  30  (22): [PMID:33007395] [10.1016/j.bmcl.2020.127578]

Source

Source(1):

• Scientific Literature