2-(6-Amino-purin-9-yl)-5-isobutylsulfanylmethyl-tetrahydro-furan-3,4-diol

ID: ALA605813

Chembl Id: CHEMBL605813

PubChem CID: 46874970

Max Phase: Preclinical

Molecular Formula: C14H21N5O3S

Molecular Weight: 339.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CSC[C@H]1OC(n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H21N5O3S/c1-7(2)3-23-4-8-10(20)11(21)14(22-8)19-6-18-9-12(15)16-5-17-13(9)19/h5-8,10-11,14,20-21H,3-4H2,1-2H3,(H2,15,16,17)/t8-,10-,11-,14?/m1/s1

Standard InChI Key:  JDDUQGRUPLKDNT-OYBGHCQBSA-N

Alternative Forms

1. Parent:

   

   ALA605813

   (3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(2-methylpropylsulfanylmethyl)oxolane-3,4-diol

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: 339.42

Molecular Weight (Monoisotopic): 339.1365

AlogP: 0.42

#Rotatable Bonds: 5

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.47

CX Basic pKa: 3.94

CX LogP: 0.53

CX LogD: 0.53

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: 0.65

References

1. Pankaskie MC, Kachur JF, Itoh T, Gordon RK, Chiang PK..  (1985)  Inhibition of muscarinic receptor binding and acetylcholine-induced contraction of guinea pig ileum by analogues of 5'-(isobutylthio)adenosine.,  28  (8): [PMID:3874962] [10.1021/jm00146a027]

2. Steere JA, Sampson PB, Honek JF..  (2002)  Synthesis of an alpha-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase.,  12  (3): [PMID:11814819] [10.1016/s0960-894x(01)00789-2]

Source

Source(1):

• Scientific Literature