2-Amino-5-guanidino-pentanoic acid [(4R,5S,6S)-5-amino-6-((2R,3R,4R)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl]-amide

ID: ALA155256

PubChem CID: 44369902

Max Phase: Preclinical

Molecular Formula: C18H38N8O7

Molecular Weight: 478.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(N)=NCCCC(N)C(=O)NCC1OC(OC2C(N)CC(N)C(O)C2O)C(N)C(O)C1O

Standard InChI:  InChI=1S/C18H38N8O7/c19-6(2-1-3-25-18(23)24)16(31)26-5-9-12(28)13(29)10(22)17(32-9)33-15-8(21)4-7(20)11(27)14(15)30/h6-15,17,27-30H,1-5,19-22H2,(H,26,31)(H4,23,24,25)

Standard InChI Key:  JPBLSVNUKDDJAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    2.4792   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -1.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542    2.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -0.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917    3.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -0.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -3.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    2.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -3.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292    0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -4.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -2.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -1.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -4.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    1.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  1  1  0
  8  9  1  0
  9  6  1  0
 10  5  1  0
 11  3  1  0
 12 13  1  0
 13 11  1  0
 14 21  2  0
 15 16  1  0
 16 18  1  0
 17 14  1  0
 18  9  1  0
 19 15  2  0
 20  2  1  0
 21 31  1  0
 22  4  1  0
 23 15  1  0
 24  5  1  0
 25 14  1  0
 26 11  1  0
 27 12  1  0
 28  8  1  0
 29 10  1  0
 30 23  1  0
 31 33  1  0
 32 23  1  0
 33 32  1  0
  4  8  1  0
 12 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA155256

   2-amino-N-[[5-amino-6-(4,6-diamino-2,3-dihydroxycyclohexyl)oxy-3,4-dihydroxyoxan-2-yl]methyl]-5-(diaminomethylideneamino)pentanamide

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: 478.55

Molecular Weight (Monoisotopic): 478.2863

AlogP: -6.58

#Rotatable Bonds: 9

Polar Surface Area: 296.96

Molecular Species: BASE

HBA: 12

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 17

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.66

CX Basic pKa: 14.75

CX LogP: -6.91

CX LogD: -12.93

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.08

Np Likeness Score: 1.48

References

1. Hamasaki K, Ueno A..  (2001)  Aminoglycoside antibiotics, neamine and its derivatives as potent inhibitors for the RNA-protein interactions derived from HIV-1 activators.,  11  (4): [PMID:11229778] [10.1016/s0960-894x(01)00005-1]

Source

Source(1):

• Scientific Literature