1-N-(Biotinyl)-amino-1,2,5-trideoxy-2,5-imino-D-mannitol

ID: ALA1171694

PubChem CID: 46911765

Max Phase: Preclinical

Molecular Formula: C16H28N4O5S

Molecular Weight: 388.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCC1SCC2NC(=O)NC21)NC[C@H]1N[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H28N4O5S/c21-6-9-15(24)14(23)8(18-9)5-17-12(22)4-2-1-3-11-13-10(7-26-11)19-16(25)20-13/h8-11,13-15,18,21,23-24H,1-7H2,(H,17,22)(H2,19,20,25)/t8-,9-,10?,11?,13?,14-,15-/m1/s1

Standard InChI Key:  RJDOSQYVCVIUIH-DFFGHCKCSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    0.3272   -6.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1518   -6.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -5.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416   -4.8724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762   -5.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -5.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -6.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6373   -6.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1260   -4.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218   -5.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369   -5.3728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -4.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661   -5.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -4.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9843   -4.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952   -5.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4134   -4.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -5.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4242   -5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8766   -5.0820    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0034   -6.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1997   -6.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861   -6.9428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3343   -7.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0882   -7.2260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1547   -8.3642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 12 14  2  0
  1  7  1  6
 13 15  1  0
  2  3  1  0
 15 16  1  0
  2  8  1  1
 16 17  1  0
  3  4  1  0
 17 18  1  0
 18 22  1  0
  3  9  1  6
  4  5  1  0
 21 19  1  0
 19 20  1  0
 20 18  1  0
 21 22  1  0
  6 10  1  0
  5  1  1  0
  9 11  1  0
  1  2  1  0
 11 12  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
  5  6  1  1
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1171694

   N-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)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: 388.49

Molecular Weight (Monoisotopic): 388.1780

AlogP: -2.12

#Rotatable Bonds: 8

Polar Surface Area: 142.95

Molecular Species: BASE

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.02

CX Basic pKa: 8.67

CX LogP: -2.63

CX LogD: -3.92

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.19

Np Likeness Score: 0.42

References

1. Pototschnig G, De Csáky CM, Burke JR, Schitter G, Stütz AE, Tarling CA, Withers SG, Wrodnigg TM..  (2010)  Synthesis and biological evaluation of novel biotin-iminoalditol conjugates.,  20  (14): [PMID:20610152] [10.1016/j.bmcl.2010.05.084]

Source

Source(1):

• Scientific Literature