(5-(1-Phenylpropyl)thiophene-2-carbonyl)-L-arginine

ID: ALA4530755

PubChem CID: 155546129

Max Phase: Preclinical

Molecular Formula: C20H26N4O3S

Molecular Weight: 402.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(c1ccccc1)c1ccc(C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)s1

Standard InChI:  InChI=1S/C20H26N4O3S/c1-2-14(13-7-4-3-5-8-13)16-10-11-17(28-16)18(25)24-15(19(26)27)9-6-12-23-20(21)22/h3-5,7-8,10-11,14-15H,2,6,9,12H2,1H3,(H,24,25)(H,26,27)(H4,21,22,23)/t14?,15-/m0/s1

Standard InChI Key:  LOIOJHXFQJHVEQ-LOACHALJSA-N

Molfile:  

 
     RDKit          2D

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   30.6508  -14.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5464  -14.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7329  -13.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3434  -14.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3753  -15.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3949  -16.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0803  -14.9181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8050  -15.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5100  -14.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8245  -16.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1194  -16.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5491  -16.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4904  -14.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1913  -13.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1719  -12.8034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8769  -12.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8573  -11.5514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6014  -12.7696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5180  -14.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1062  -13.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5284  -13.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1171  -12.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2913  -12.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8783  -13.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2877  -13.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1008  -15.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2758  -15.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
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  5  1  1  0
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  8  9  1  0
  9 10  1  1
  9 11  1  0
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 11 13  2  0
 10 14  1  0
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 16 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 20 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4530755

   ---

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: 402.52

Molecular Weight (Monoisotopic): 402.1726

AlogP: 2.74

#Rotatable Bonds: 10

Polar Surface Area: 128.30

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.64

CX Basic pKa: 11.99

CX LogP: 1.41

CX LogD: 1.41

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.24

Np Likeness Score: -0.31

References

1. Rowley JA, Reid RC, Poon EKY, Wu KC, Lim J, Lohman RJ, Hamidon JK, Yau MK, Halili MA, Durek T, Iyer A, Fairlie DP..  (2020)  Potent Thiophene Antagonists of Human Complement C3a Receptor with Anti-Inflammatory Activity.,  63  (2): [PMID:31910011] [10.1021/acs.jmedchem.9b00927]

Source

Source(1):

• Scientific Literature