alpha-2'-deoxythioguanosine

ID: ALA3230221

Cas Number: 2133-81-5

PubChem CID: 3005835

Max Phase: Preclinical

Molecular Formula: C10H13N5O3S

Molecular Weight: 283.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c(ncn2[C@@H]2C[C@H](O)[C@@H](CO)O2)c(=S)[nH]1

Standard InChI:  InChI=1S/C10H13N5O3S/c11-10-13-8-7(9(19)14-10)12-3-15(8)6-1-4(17)5(2-16)18-6/h3-6,16-17H,1-2H2,(H3,11,13,14,19)/t4-,5+,6-/m0/s1

Standard InChI Key:  SCVJRXQHFJXZFZ-JKUQZMGJSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    3.7475   -3.1078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7475   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -4.3295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1580   -3.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9362   -4.1789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4172   -3.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363   -2.8551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -1.8779    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0404   -4.3346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887   -4.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7090   -5.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1892   -6.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9665   -6.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9665   -5.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9367   -7.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6276   -6.5040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1373   -7.2232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  2  0
  2 11  1  0
 12  7  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 14 17  1  1
 15 18  1  6
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3230221

   alpha-Thiodeoxyguanosine

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: 283.31

Molecular Weight (Monoisotopic): 283.0739

AlogP: -0.29

#Rotatable Bonds: 2

Polar Surface Area: 122.21

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.99

CX Basic pKa: 1.46

CX LogP: -0.92

CX LogD: -0.92

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.56

Np Likeness Score: 0.91

References

1. Acton EM, Goerner RN, Uh HS, Ryan KJ, Henry DW, Cass CE, LePage GA..  (1979)  Improved antitumor effects in 3'-branched homologues of 2'-deoxythioguanosine. Synthesis and evaluation of thioguanine nucleosides of 2,3-dideoxy-3-(hydroxymethyl)-D-erythro-pentofuranose.,  22  (5): [PMID:582321] [10.1021/jm00191a012]

2. Martinez AP, Lee WW, Henry DW..  (1977)  Potential antitumor agents. Some sulfur-substituted derivatives of alpha- and beta-2'-deoxythioguanosine.,  20  (3): [PMID:845866] [10.1021/jm00213a005]

Source

Source(1):

• Scientific Literature