(5-(Bis(4-chlorophenyl)methyl)-3-methylthiophene-2-carbonyl)-L-arginine

ID: ALA4459627

PubChem CID: 145996525

Product Number: J611283, Order Now?

Max Phase: Preclinical

Molecular Formula: C25H26Cl2N4O3S

Molecular Weight: 533.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)sc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C25H26Cl2N4O3S/c1-14-13-20(21(15-4-8-17(26)9-5-15)16-6-10-18(27)11-7-16)35-22(14)23(32)31-19(24(33)34)3-2-12-30-25(28)29/h4-11,13,19,21H,2-3,12H2,1H3,(H,31,32)(H,33,34)(H4,28,29,30)/t19-/m0/s1

Standard InChI Key:  OHRIKWUZKGNQKQ-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

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   30.4162  -25.2697    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.1583  -24.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0545  -24.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2446  -23.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8526  -24.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8797  -25.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8991  -26.1315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   33.3029  -25.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0048  -24.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3224  -26.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6205  -26.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0438  -26.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9854  -24.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6832  -23.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637  -22.7798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3656  -22.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.0870  -22.7461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0309  -24.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6250  -23.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6197  -25.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7982  -25.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3870  -26.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7966  -26.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6216  -26.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0291  -26.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0448  -23.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6396  -22.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8179  -22.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4032  -23.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8108  -23.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6486  -23.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4128  -21.8251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.3880  -27.5071    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  5  1  1  0
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  9 10  1  1
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 17 18  1  0
 17 19  2  0
  5 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 21 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 21  1  0
  3 33  1  0
 30 34  1  0
 25 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4459627

   JR14a

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: 533.48

Molecular Weight (Monoisotopic): 532.1103

AlogP: 4.99

#Rotatable Bonds: 10

Polar Surface Area: 128.30

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.64

CX Basic pKa: 11.97

CX LogP: 3.82

CX LogD: 3.82

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.14

Np Likeness Score: -0.40

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