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

ID: ALA605227

Chembl Id: CHEMBL605227

PubChem CID: 46874031

Max Phase: Preclinical

Molecular Formula: C21H38N8O3S

Molecular Weight: 482.66

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H38N8O3S/c22-7-4-10-25-9-3-1-2-5-14(6-8-23)33-11-15-17(30)18(31)21(32-15)29-13-28-16-19(24)26-12-27-20(16)29/h12-15,17-18,21,25,30-31H,1-11,22-23H2,(H2,24,26,27)/t14?,15-,17-,18-,21?/m1/s1

Standard InChI Key:  IYEWZPHRHXRMCW-RXHHNXKZSA-N

Alternative Forms

1. Parent:

   

   ALA605227

   (2S,3S,4R)-2-[[1-amino-8-(3-aminopropylamino)octan-3-yl]sulfanylmethyl]-5-(6-aminopurin-9-yl)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: 482.66

Molecular Weight (Monoisotopic): 482.2788

AlogP: -0.02

#Rotatable Bonds: 15

Polar Surface Area: 183.38

Molecular Species: BASE

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.47

CX Basic pKa: 10.59

CX LogP: -1.13

CX LogD: -7.37

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.19

Np Likeness Score: 0.66

References

1. Woster PM, Black AY, Duff KJ, Coward JK, Pegg AE..  (1989)  Synthesis and biological evaluation of S-adenosyl-1,12-diamino-3-thio-9-azadodecane, a multisubstrate adduct inhibitor of spermine synthase.,  32  (6): [PMID:2724300] [10.1021/jm00126a026]

2. Lakanen JR, Pegg AE, Coward JK..  (1995)  Synthesis and biochemical evaluation of adenosylspermidine, a nucleoside-polyamine adduct inhibitor of spermidine synthase.,  38  (14): [PMID:7629810] [10.1021/jm00014a023]

Source

Source(1):

• Scientific Literature