6'-(R)-Methyl-paromamine

ID: ALA1165271

PubChem CID: 46907084

Max Phase: Preclinical

Molecular Formula: C13H27N3O7

Molecular Weight: 337.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](O)[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C13H27N3O7/c1-3(17)11-10(21)8(19)6(16)13(22-11)23-12-5(15)2-4(14)7(18)9(12)20/h3-13,17-21H,2,14-16H2,1H3/t3-,4+,5-,6+,7-,8+,9+,10-,11+,12+,13+/m0/s1

Standard InChI Key:  WCWFAVKENOLGNG-ZDDMDELRSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   11.8717  -18.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8709  -19.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5862  -19.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2956  -19.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2983  -18.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5811  -18.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0142  -18.1451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5853  -20.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1572  -19.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4418  -19.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4447  -18.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7331  -18.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0140  -18.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0149  -19.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7346  -19.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7315  -17.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1483  -18.9672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0190  -16.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4410  -17.7252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0138  -19.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1569  -18.1493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7351  -20.6302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999  -19.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3006  -18.1482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4487  -16.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  5  7  1  1
  3  8  1  1
  2  9  1  6
  9 10  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 10 17  1  1
 16 18  1  6
 12 19  1  6
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
 15 22  1  6
 14 23  1  1
  1 21  1  1
 13 24  1  6
  4 20  1  6
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1165271

   (2R,3S,4R,5R,6S)-5-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-2-[(1S)-1-hydroxyethyl]oxane-3,4-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: 337.37

Molecular Weight (Monoisotopic): 337.1849

AlogP: -4.69

#Rotatable Bonds: 3

Polar Surface Area: 197.67

Molecular Species: BASE

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.63

CX Basic pKa: 9.15

CX LogP: -4.77

CX LogD: -7.76

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.25

Np Likeness Score: 1.86

References

1. Nudelman I, Glikin D, Smolkin B, Hainrichson M, Belakhov V, Baasov T..  (2010)  Repairing faulty genes by aminoglycosides: development of new derivatives of geneticin (G418) with enhanced suppression of diseases-causing nonsense mutations.,  18  (11): [PMID:20409719] [10.1016/j.bmc.2010.03.060]

Source

Source(1):

• Scientific Literature