4,4'-Di[3-(hydroxyethyl)guanidino]diphenylmethane dihydrochloride

ID: ALA4759811

PubChem CID: 162658283

Max Phase: Preclinical

Molecular Formula: C19H28Cl2N6O2

Molecular Weight: 370.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(NCCO)Nc1ccc(Cc2ccc(NC(=N)NCCO)cc2)cc1

Standard InChI:  InChI=1S/C19H26N6O2.2ClH/c20-18(22-9-11-26)24-16-5-1-14(2-6-16)13-15-3-7-17(8-4-15)25-19(21)23-10-12-27;;/h1-8,26-27H,9-13H2,(H3,20,22,24)(H3,21,23,25);2*1H

Standard InChI Key:  JUWKWLLQWHWVJJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
   41.5446  -11.3732    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.2332   -9.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2321   -9.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9469  -10.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6634   -9.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6606   -9.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9451   -8.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3735   -8.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0896   -9.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0893   -9.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8045  -10.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5185   -9.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5126   -9.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7969   -8.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2350  -10.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9475   -9.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5172  -10.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8032   -9.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8038   -9.0308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0883  -10.2677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3741   -9.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6593  -10.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6640  -10.2392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3765   -9.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9432   -9.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0930  -10.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8054   -9.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9451   -9.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4545   -7.9259    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
  3 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 16 25  2  0
 24 26  1  0
 26 27  1  0
 22 28  1  0
M  END

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: 370.46

Molecular Weight (Monoisotopic): 370.2117

AlogP: 1.13

#Rotatable Bonds: 8

Polar Surface Area: 136.28

Molecular Species: BASE

HBA: 4

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.87

CX LogP: 1.19

CX LogD: -1.15

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: -0.17

References

1. McMullan M,Kelly B,Mihigo HB,Keogh AP,Rodriguez F,Brocos-Mosquera I,García-Bea A,Miranda-Azpiazu P,Callado LF,Rozas I.  (2021)  Di-aryl guanidinium derivatives: Towards improved α2-Adrenergic affinity and antagonist activity.,  209  [PMID:33139112] [10.1016/j.ejmech.2020.112947]

Source

Source(1):

• Scientific Literature