(2S,3S,4R,5R,6R)-6-((2S,3R,4R,5R,6R)-3-acetamido-2-((2S,3S,4R,5R,6R)-2-carboxy-6-(4,20-dioxo-24-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-7,10,13,16-tetraoxa-3,19-diazatetracosyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-((2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylic acid

ID: ALA1950105

PubChem CID: 57399964

Max Phase: Preclinical

Molecular Formula: C51H84N6O30S

Molecular Weight: 1293.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@H](OCCNC(=O)CCOCCOCCOCCOCCNC(=O)CCCC[C@@H]5SC[C@@H]6NC(=O)N[C@@H]65)O[C@@H]4C(=O)O)[C@@H]3NC(C)=O)O[C@@H]2C(=O)O)O[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C51H84N6O30S/c1-22(60)54-31-35(66)33(64)25(19-58)81-47(31)84-42-37(68)39(70)50(87-44(42)46(73)74)83-40-32(55-23(2)61)48(82-26(20-59)34(40)65)85-41-36(67)38(69)49(86-43(41)45(71)72)80-12-9-53-29(63)7-10-76-13-15-78-17-18-79-16-14-77-11-8-52-28(62)6-4-3-5-27-30-24(21-88-27)56-51(75)57-30/h24-27,30-44,47-50,58-59,64-70H,3-21H2,1-2H3,(H,52,62)(H,53,63)(H,54,60)(H,55,61)(H,71,72)(H,73,74)(H2,56,57,75)/t24-,25+,26+,27-,30-,31+,32+,33-,34-,35+,36+,37+,38+,39+,40+,41-,42-,43-,44-,47-,48-,49+,50+/m0/s1

Standard InChI Key:  NWNVIKIQYNCUAD-DAKXWSGMSA-N

Molfile:  

     RDKit          2D

 93 98  0  0  0  0  0  0  0  0999 V2000
   18.7184   -1.1992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0610   -0.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3795   -1.1641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4423   -1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6148   -1.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3441   -2.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9983   -3.2359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.6746   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0829    0.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7889   -1.9327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2606   -1.9970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6215   -3.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9113   -2.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1886   -3.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4846   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7727   -3.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0585   -2.6400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7405   -3.8904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3380   -3.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6322   -2.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9038   -3.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2062   -2.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4778   -2.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7800   -2.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0458   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3410   -2.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6194   -2.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9146   -2.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4863   -2.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -2.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -2.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3342   -2.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -2.3837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3157   -3.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -2.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010   -2.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -2.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5232   -5.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0525   -7.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739   -7.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899   -6.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0802   -6.1983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5114   -6.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2210   -6.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9387   -6.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2052   -7.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4836   -7.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9109   -7.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8992   -8.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8111   -4.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -8.2760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -4.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510   -6.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -6.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -6.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -5.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817   -6.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -7.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6324   -7.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -7.3807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -8.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776   -9.0286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3071   -9.0718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -6.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0988   -6.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8240   -6.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8437   -5.2546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5258   -6.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5061   -7.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060   -7.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7809   -7.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0755   -7.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -8.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0305   -8.9471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5459   -3.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614   -3.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8849   -3.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1382   -4.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -5.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926   -4.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692   -3.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -5.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -4.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0372   -6.0050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -4.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5919   -4.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737   -5.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2287   -6.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273   -6.8711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1329   -5.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0879   -7.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 32 33  1  0
 15 16  1  0
 33 34  1  0
  7  8  1  0
 33 35  2  0
 16 17  1  0
 34 36  1  0
  8  4  1  0
 36 37  1  0
 16 18  2  0
  4  5  1  0
 17 19  1  0
  2  9  2  0
 19 20  1  0
 20 21  1  0
  5 10  1  6
 21 22  1  0
  4  1  1  0
 22 23  1  0
  4 11  1  6
 23 24  1  0
  1  2  1  0
 24 25  1  0
  6 12  1  1
 25 26  1  0
  2  3  1  0
 26 27  1  0
 12 13  1  0
 27 28  1  0
  3  5  1  0
 28 29  1  0
 13 14  1  0
 29 30  1  0
  5  6  1  0
 30 31  1  0
 42 44  1  0
 44 39  1  1
 44 45  1  0
 45 46  1  1
 45 47  1  0
 47 48  1  0
 47 49  1  1
 49 50  1  0
 41 48  1  0
 43 51  1  0
 51 52  1  0
 41 53  1  6
 51 54  2  0
 56 55  1  0
 56 57  1  0
 57 58  1  6
 57 59  1  0
 59 60  1  0
 60 40  1  6
 60 61  1  0
 61 62  1  0
 61 63  1  1
 63 64  1  0
 56 62  1  0
 63 65  2  0
 67 66  1  0
 67 68  1  0
 68 69  1  6
 68 70  1  0
 70 55  1  1
 70 71  1  0
 71 72  1  1
 71 73  1  0
 73 74  1  0
 73 75  1  1
 75 76  1  0
 67 74  1  0
 77 38  1  1
 77 78  1  0
 78 79  1  6
 78 80  1  0
 80 81  1  0
 81 66  1  6
 81 82  1  0
 82 83  1  0
 82 84  1  1
 84 85  1  0
 77 83  1  0
 84 86  2  0
 69 87  1  0
 87 88  2  0
 41 40  1  0
 87 89  1  0
 41 42  1  0
 56 90  1  6
 42 43  1  6
 67 91  1  6
 38 37  1  0
 14 15  1  0
 80 92  1  1
 31 32  1  0
 59 93  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1950105

   (2S,3S,4R,5R,6R)-6-[2-[3-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]ethoxy]-3-[(2S,3R,4R,5R,6R)-3-acetamido-4-[(2R,3R,4R,5S,6S)-5-[(2S,3R,4R,5R,6R)-3-aceta

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: 1293.31

Molecular Weight (Monoisotopic): 1292.4953

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Tamura J, Tsutsumishita-Nakai N, Nakao Y, Kawano M, Kato S, Takeda N, Nadanaka S, Kitagawa H..  (2012)  Synthesis and interaction with midkine of biotinylated chondroitin sulfate tetrasaccharides.,  22  (3): [PMID:22237251] [10.1016/j.bmcl.2011.12.054]

Source

Source(1):

• Scientific Literature