(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(methylsulfinylmethyl)tetrahydrofuran-3-yl 6-bromo-5-hydroxy-1H-indole-3-carboxylate

ID: ALA2409549

PubChem CID: 71814323

Max Phase: Preclinical

Molecular Formula: C20H19BrN6O6S

Molecular Weight: 551.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[S+]([O-])C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OC(=O)c1c[nH]c2cc(Br)c(O)cc12

Standard InChI:  InChI=1S/C20H19BrN6O6S/c1-34(31)5-13-16(33-20(30)9-4-23-11-3-10(21)12(28)2-8(9)11)15(29)19(32-13)27-7-26-14-17(22)24-6-25-18(14)27/h2-4,6-7,13,15-16,19,23,28-29H,5H2,1H3,(H2,22,24,25)/t13-,15-,16-,19-,34?/m1/s1

Standard InChI Key:  YRDDCVZIQCURLZ-XODDSCPXSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    9.7518   -8.6604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4378   -6.9014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0900   -7.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2435   -6.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3359   -5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5748   -5.5733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5067   -8.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0154   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2815   -7.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9536   -8.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1952   -8.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0895   -5.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9077   -7.2129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7538   -6.0596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6675   -6.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3426   -8.4689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1757   -4.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1284   -9.8146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4751   -9.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0363   -9.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7493   -7.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5117  -10.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7213  -10.1155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6854  -11.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3568  -12.3469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4425  -11.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5444  -12.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1281  -11.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2995  -11.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8862  -12.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3076  -13.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1348  -13.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0555  -12.5280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8971  -13.9658    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1
  4  2  1  0
  5  4  2  0
  6  8  2  0
  7  3  1  0
  8  2  1  0
  9  3  1  0
 10  7  1  0
 11  9  1  0
 12  5  1  0
 13  4  1  0
 14 15  1  0
 15 13  2  0
  7 16  1  6
 17 12  1  0
 10 18  1  6
 11 19  1  1
  5  6  1  0
 10 11  1  0
 14 12  2  0
 19  1  1  0
  1 20  1  0
  1 21  1  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 28  1  0
 27 25  1  0
 25 26  1  0
 26 24  2  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 30 33  1  0
 31 34  1  0
M  CHG  2   1   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2409549

   [(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(methylsulfinylmethyl)oxolan-3-yl] 6-bromo-5-hydroxy-1H-indole-3-carboxylate

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: 551.38

Molecular Weight (Monoisotopic): 550.0270

AlogP: 1.22

#Rotatable Bonds: 5

Polar Surface Area: 184.46

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.63

CX Basic pKa: 3.94

CX LogP: 0.23

CX LogD: 0.03

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 0.81

References

1. Li JL, Kim EL, Wang H, Hong J, Shin S, Lee CK, Jung JH..  (2013)  Epimeric methylsulfinyladenosine derivatives from the marine ascidian Herdmania momus.,  23  (16): [PMID:23810281] [10.1016/j.bmcl.2013.05.097]

2. Li JL, Kim EL, Wang H, Hong J, Shin S, Lee CK, Jung JH..  (2013)  Epimeric methylsulfinyladenosine derivatives from the marine ascidian Herdmania momus.,  23  (16): [PMID:23810281] [10.1016/j.bmcl.2013.05.097]

Source

Source(1):

• Scientific Literature