Paromamine

ID: ALA606552

Cas Number: 534-47-4

PubChem CID: 439560

Max Phase: Preclinical

Molecular Formula: C12H25N3O7

Molecular Weight: 323.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Paromamine | Paromamine|534-47-4|Neomycin D|WGK534PM7Q|UNII-WGK534PM7Q|CHEBI:7933|(2R,3S,4R,5R,6S)-5-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-2-(hydroxymethyl)oxane-3,4-diol|(1R)-O4-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-2-deoxy-streptamine|4-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-2-deoxy-D-streptamine|D-Streptamine, 4-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-2-deoxy-|(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside|GENShow More⌵

Synonyms from Alternative Forms(1): Paromamine Sulfate

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

Standard InChI:  InChI=1S/C12H25N3O7/c13-3-1-4(14)11(10(20)7(3)17)22-12-6(15)9(19)8(18)5(2-16)21-12/h3-12,16-20H,1-2,13-15H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1

Standard InChI Key:  JGSMDVGTXBPWIM-HKEUSBCWSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
    4.2125    1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245    0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6365    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6365    1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245    2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4968    2.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3504    0.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4986    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245    3.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3522    2.2104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836    0.9729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3492   -0.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6275   -0.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6243   -1.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3364   -1.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0533   -1.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0581   -0.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156   -0.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3321   -2.7360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7739   -0.2629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9077   -1.9024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  8  1  6
 13 14  1  0
  5  6  1  0
  1  7  1  1
  4  8  1  1
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  1  2  1  0
 14 19  1  1
  2  9  1  6
 16 20  1  1
  1  6  1  0
 18 21  1  1
  6 10  1  6
 15 22  1  6
  2  3  1  0
  5 11  1  1
  3  4  1  0
  9 12  1  0
  4  5  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA606552

   PAROMAMINE SULFATE

2. Parent:

   

   ALA606552

   PAROMAMINE

Molecule Features

Natural Product: Yes

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: 323.35

Molecular Weight (Monoisotopic): 323.1693

AlogP: -5.08

#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: 12.64

CX Basic pKa: 9.15

CX LogP: -5.18

CX LogD: -8.18

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.25

Np Likeness Score: 2.02

References

1. Cashman DJ, Rife JP, Kellogg GE..  (2001)  Which aminoglycoside ring is most important for binding? A hydropathic analysis of gentamicin, paromomycin, and analogues.,  11  (2): [PMID:11206440] [10.1016/s0960-894x(00)00615-6]

2. 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]

3. Zimmermann L, Bussière A, Ouberai M, Baussanne I, Jolivalt C, Mingeot-Leclercq MP, Décout JL..  (2013)  Tuning the antibacterial activity of amphiphilic neamine derivatives and comparison to paromamine homologues.,  56  (19): [PMID:24083676] [10.1021/jm401148j]

4. Sabbavarapu NM, Shavit M, Degani Y, Smolkin B, Belakhov V, Baasov T..  (2016)  Design of Novel Aminoglycoside Derivatives with Enhanced Suppression of Diseases-Causing Nonsense Mutations.,  7  (4): [PMID:27096052] [10.1021/acsmedchemlett.6b00006]

Source

Source(1):

• Scientific Literature