N-(2-(5-((2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((naphthalen-2-ylmethoxy)methyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-ylthio)pentylthio)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide

ID: ALA1077234

PubChem CID: 46881685

Max Phase: Preclinical

Molecular Formula: C42H56N2O12S3

Molecular Weight: 877.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1cccc2c(S(=O)(=O)NCCSCCCCCS[C@@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](COCc5ccc6ccccc6c5)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)cccc12

Standard InChI:  InChI=1S/C42H56N2O12S3/c1-44(2)31-14-8-13-30-29(31)12-9-15-34(30)59(51,52)43-18-21-57-19-6-3-7-20-58-42-39(50)37(48)40(32(23-45)55-42)56-41-38(49)36(47)35(46)33(54-41)25-53-24-26-16-17-27-10-4-5-11-28(27)22-26/h4-5,8-17,22,32-33,35-43,45-50H,3,6-7,18-21,23-25H2,1-2H3/t32-,33-,35-,36+,37-,38-,39-,40-,41-,42+/m1/s1

Standard InChI Key:  SIAZQINJGPVCHF-NYDGXXASSA-N

Molfile:  

     RDKit          2D

 60 65  0  0  0  0  0  0  0  0999 V2000
   13.0754   -0.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7270   -0.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2969    0.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4730    0.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3299   -0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5046   -0.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1061   -1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5358   -2.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3641   -2.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7548   -1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5517   -0.0350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9819   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9506    0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2812   -1.5346    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4545   -1.5351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2903   -2.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2740   -0.7096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7355   -1.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0274   -1.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3037   -1.1565    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5986   -1.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8775   -1.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725   -1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4514   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464   -1.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0295   -1.2159    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -1.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6009   -1.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9040   -2.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6255   -2.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3378   -2.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593   -2.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360   -3.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1747   -1.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -0.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942   -2.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4740   -2.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638   -1.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478   -1.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355   -1.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439   -2.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -2.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -3.3206    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742   -3.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6632   -2.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -1.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7405   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220   -0.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148    0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    2.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208    2.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233    1.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8522    2.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5624    1.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488    1.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8289    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 14 15  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  6
 14 16  2  0
 31 34  1  1
  7  8  2  0
 29 35  1  1
 14 17  2  0
 35 36  1  0
  3  4  2  0
 30 37  1  6
 15 18  1  0
 37 38  1  0
 38 39  1  0
  8  9  1  0
 18 19  1  0
  4  1  1  0
 19 20  1  0
  9 10  2  0
 38 43  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 20 21  1  0
 38 44  1  1
 10  5  1  0
 43 45  1  6
 21 22  1  0
 42 46  1  1
  5  2  2  0
 41 47  1  6
 22 23  1  0
 40 48  1  1
  2 11  1  0
 48 49  1  0
 23 24  1  0
 49 50  1  0
  1  6  2  0
 50 51  1  0
 24 25  1  0
 51 52  2  0
 11 12  1  0
 52 53  1  0
 53 56  2  0
 25 26  1  0
 55 54  2  0
 54 51  1  0
  5  6  1  0
 27 26  1  1
 55 56  1  0
 27 28  1  0
 56 57  1  0
 11 13  1  0
 57 58  2  0
  2  3  1  0
 58 59  1  0
  7 14  1  0
 59 60  2  0
 60 55  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077234

   N-[2-[5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylpentylsulfanyl]ethyl]-5-(dimethylamino)naphthalene-1-sulfonamide

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: 877.11

Molecular Weight (Monoisotopic): 876.2995

AlogP: 2.82

#Rotatable Bonds: 20

Polar Surface Area: 207.71

Molecular Species: NEUTRAL

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.91

CX Basic pKa: 4.63

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 4

Heavy Atoms: 59

QED Weighted: 0.06

Np Likeness Score: 0.08

References

1. Oka H, Koyama T, Hatano K, Terunuma D, Matsuoka K..  (2010)  Simple and conveniently accessible bi-fluorescence-labeled substrates for amylases.,  20  (6): [PMID:20171095] [10.1016/j.bmcl.2010.01.117]

2. Oka H, Koyama T, Hatano K, Matsuoka K..  (2012)  Synthetic studies of bi-fluorescence-labeled maltooligosaccharides as substrates for α-amylase on the basis of fluorescence resonance energy transfer (FRET).,  20  (1): [PMID:22100259] [10.1016/j.bmc.2011.10.065]

Source

Source(1):

• Scientific Literature