6'-N-(2-Hydroxyethyl)sisomicin

ID: ALA3245223

PubChem CID: 90672130

Max Phase: Preclinical

Molecular Formula: C21H41N5O8

Molecular Weight: 491.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(CNCCO)=CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

Standard InChI:  InChI=1S/C21H41N5O8/c1-21(30)9-31-20(15(29)18(21)25-2)34-17-13(24)7-12(23)16(14(17)28)33-19-11(22)4-3-10(32-19)8-26-5-6-27/h3,11-20,25-30H,4-9,22-24H2,1-2H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1

Standard InChI Key:  DWSIEZPHSFCNAT-MQDUPKMGSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
   14.4215  -13.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7165  -14.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0307  -16.2156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1346  -14.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7275  -14.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4342  -15.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1463  -14.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8396  -13.7367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0161  -15.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7611  -17.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7466  -16.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2028  -13.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0534  -12.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3023  -12.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2898  -11.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4697  -12.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4269  -12.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7229  -12.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8569  -11.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5941  -12.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5817  -11.3214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7103  -11.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6479  -13.3418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1861  -12.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9939  -11.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7699  -13.0252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818  -12.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4280  -10.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0313  -13.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7282  -11.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0188  -12.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3976  -11.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1446  -11.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5234  -12.3003    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4489  -11.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4759  -17.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0
  9  5  1  0
  6  7  1  0
  4  1  1  0
  6  5  2  0
  2  1  1  0
  3  9  1  0
 11 10  1  0
  4  8  1  6
  7  4  1  0
  3 11  1  0
 24 27  1  0
 22 25  1  0
 25 15  1  0
 31 29  1  6
 18 23  1  6
 33 35  1  0
 28 35  1  0
 16 24  1  0
 16 26  1  1
 19 27  1  0
 20 14  1  0
 35 30  1  1
 33 19  1  0
 17 18  1  0
 22 32  1  6
 18 31  1  0
 35 16  1  0
 14 34  1  6
 27 20  1  6
 22 18  1  0
 15 21  1  6
 13 26  1  0
 24 12  1  6
 15 14  1  0
 31 14  1  0
  1 17  1  6
 10 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245223

   (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.59

Molecular Weight (Monoisotopic): 491.2955

AlogP: -4.23

#Rotatable Bonds: 9

Polar Surface Area: 219.96

Molecular Species: BASE

HBA: 13

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.55

CX Basic pKa: 9.59

CX LogP: -4.58

CX LogD: -11.32

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: 1.66

References

1. Davies DH, Mallams AK, Counelis M, Loebenberg D, Moss EL, Waitz JA..  (1978)  Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, Antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C.,  21  (2): [PMID:413921] [10.1021/jm00200a009]

Source

Source(1):

• Scientific Literature