2-[6-Amino-1-(2-amino-ethyl)-hexylsulfanylmethyl]-5-(6-amino-purin-9-yl)-tetrahydro-furan-3,4-diol

ID: ALA2021377

Chembl Id: CHEMBL2021377

PubChem CID: 446530

Max Phase: Preclinical

Molecular Formula: C18H31N7O3S

Molecular Weight: 425.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCCC[C@H](CCN)SC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H31N7O3S/c19-6-3-1-2-4-11(5-7-20)29-8-12-14(26)15(27)18(28-12)25-10-24-13-16(21)22-9-23-17(13)25/h9-12,14-15,18,26-27H,1-8,19-20H2,(H2,21,22,23)/t11-,12-,14-,15-,18-/m1/s1

Standard InChI Key:  YETXSQDQSWLLJR-AJKMGBEJSA-N

Alternative Forms

1. Parent:

   

   ALA2021377

   (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-[[(3R)-1,8-diaminooctan-3-yl]sulfanylmethyl]oxolane-3,4-diol

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: 425.56

Molecular Weight (Monoisotopic): 425.2209

AlogP: 0.00

#Rotatable Bonds: 11

Polar Surface Area: 171.35

Molecular Species: BASE

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.47

CX Basic pKa: 10.49

CX LogP: -0.82

CX LogD: -6.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: 0.83

References

1. Liu C, Coward JK..  (1991)  Stereospecific synthesis of (R)- and (S)-S-adenosyl-1,8-diamino-3-thiooctane, a potent inhibitor of polyamine biosynthesis. Comparison of asymmetric induction vs enantiomeric synthesis.,  34  (7): [PMID:2066981] [10.1021/jm00111a026]

Source

Source(1):

• Scientific Literature