1-[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]guanidine dihydrochloride

ID: ALA4878150

PubChem CID: 164627106

Max Phase: Preclinical

Molecular Formula: C21H28Cl2N4O4

Molecular Weight: 398.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1ccc2c(cc1=O)[C@@H](NC(=N)N)CCc1cc(OC)c(OC)c(OC)c1-2.Cl.Cl

Standard InChI:  InChI=1S/C21H26N4O4.2ClH/c1-24-15-8-6-12-13(10-16(15)26)14(25-21(22)23)7-5-11-9-17(27-2)19(28-3)20(29-4)18(11)12;;/h6,8-10,14H,5,7H2,1-4H3,(H,24,26)(H4,22,23,25);2*1H/t14-;;/m0../s1

Standard InChI Key:  YOOAGOPYZHOKJF-UTLKBRERSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    8.3164  -19.5053    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0020  -15.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008  -16.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7048  -17.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030  -15.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4109  -16.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4116  -15.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0535  -15.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8547  -15.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078  -16.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0535  -17.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8570  -16.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5062  -17.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6928  -17.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5114  -18.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564  -18.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654  -18.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0490  -19.6054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511  -20.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2445  -18.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0208  -16.2143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4279  -15.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2409  -15.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056  -17.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2969  -17.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983  -15.4112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2981  -14.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937  -16.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025  -18.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0177  -14.7989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5121  -15.2377    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  6  2  0
  7  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  6 11  1  0
  8  9  1  0
  9 10  1  0
 12 10  1  0
 11 12  1  0
 12 13  2  0
 11 14  2  0
 13 15  1  0
 14 16  1  0
 15 17  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 15 20  2  0
 10 21  1  6
 21 22  1  0
 22 23  1  0
  4 24  1  0
  3 25  1  0
  2 26  1  0
 26 27  1  0
 25 28  1  0
 24 29  1  0
 22 30  2  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: 398.46

Molecular Weight (Monoisotopic): 398.1954

AlogP: 2.25

#Rotatable Bonds: 5

Polar Surface Area: 118.69

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.98

CX LogP: 0.99

CX LogD: -1.42

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: 0.75

References

1. Krzywik J, Maj E, Nasulewicz-Goldeman A, Mozga W, Wietrzyk J, Huczyński A..  (2021)  Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.,  47  [PMID:34116158] [10.1016/j.bmcl.2021.128197]

Source

Source(1):

• Scientific Literature