Butirosin B

ID: ALA605012

PubChem CID: 46873952

Max Phase: Preclinical

Molecular Formula: C21H41N5O12

Molecular Weight: 555.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H41N5O12/c22-2-1-8(28)19(34)26-7-3-6(24)17(37-20-11(25)15(32)13(30)9(4-23)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21/h6-18,20-21,27-33H,1-5,22-25H2,(H,26,34)/t6-,7+,8?,9+,10+,11+,12-,13+,14+,15+,16+,17+,18-,20+,21-/m0/s1

Standard InChI Key:  XEQLFNPSYWZPOW-QDHZCZDFSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
    3.6375   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -2.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -2.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -3.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -1.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -4.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -1.6458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -0.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -0.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -6.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -6.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -2.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -2.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -3.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0595   -3.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -4.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -5.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7396   -3.7419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -0.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7710   -0.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652   -0.9096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 10  3  1  0
 11  1  1  0
  5 12  1  6
 13 11  1  0
 14  6  1  0
 15 16  1  0
 16  9  1  0
 17 10  1  0
 13 18  1  1
 19 18  1  0
 20  5  1  0
 21 13  1  0
 22 19  2  0
 23 29  1  0
 24 19  1  0
  6 25  1  6
 14 26  1  6
 27 24  1  0
 28 24  1  0
 29 27  1  0
 20 21  1  0
 14 17  1  0
  7 15  1  0
 15 30  1  6
  2 12  1  6
 11 31  1  6
  3  8  1  1
  7 32  1  1
  4  2  1  0
 17 33  1  1
  5  1  1  0
 33 34  1  0
  6  3  1  0
  4 35  1  6
  7  4  1  0
 16 36  1  1
  1  8  1  6
 36 37  1  0
  9  2  1  0
 20 38  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA605012

   BUTIROSIN B

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: 555.58

Molecular Weight (Monoisotopic): 555.2752

AlogP: -7.79

#Rotatable Bonds: 10

Polar Surface Area: 311.71

Molecular Species: BASE

HBA: 16

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 16

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.08

CX Basic pKa: 9.61

CX LogP: -7.95

CX LogD: -13.85

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.12

Np Likeness Score: 1.54

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]

Source

Source(1):

• Scientific Literature