Phosphoric acid mono-(3,4-dihydroxy-5-{6-[8-(2-iodo-acetylamino)-octylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl) ester

ID: ALA3278434

Chembl Id: CHEMBL3278434

PubChem CID: 90680273

Max Phase: Preclinical

Molecular Formula: C20H32IN6O8P

Molecular Weight: 642.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CI)NCCCCCCCCNc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H32IN6O8P/c21-9-14(28)22-7-5-3-1-2-4-6-8-23-18-15-19(25-11-24-18)27(12-26-15)20-17(30)16(29)13(35-20)10-34-36(31,32)33/h11-13,16-17,20,29-30H,1-10H2,(H,22,28)(H,23,24,25)(H2,31,32,33)/t13-,16-,17-,20-/m1/s1

Standard InChI Key:  XUMUKPAVDQQLEB-AEVYOOLXSA-N

Alternative Forms

1. Parent:

   

   ALA3278434

   [(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-[8-[(2-iodoacetyl)amino]octylamino]purin-9-yl]oxolan-2-yl]methyl dihydrogen phosphate

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: 642.39

Molecular Weight (Monoisotopic): 642.1064

AlogP: 0.86

#Rotatable Bonds: 15

Polar Surface Area: 201.18

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.22

CX Basic pKa: 4.71

CX LogP: -1.91

CX LogD: -3.12

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.07

Np Likeness Score: 0.47

References

1. Hampton A, Picker D, Nealy KA, Maeda M..  (1982)  Use of adenine nucleotide derivatives to assess the potential of exo-active-site-directed reagents as species- or isozyme-specific enzyme inactivators. 4. Interactions of adenosine 5'-triphosphate derivatives with adenylate kinases from Escherichia coli and rat tissues.,  25  (4): [PMID:6279845] [10.1021/jm00346a010]

2. Hampton A, Kappler F, Maeda M, Patel AD..  (1978)  Use of adenine nucleotide derivatives to assess the potential of exo-active-site-directed reagents as species- or isozyme-specific enzyme inactivators. 2. Isozyme-specific inactivation of a mammalian enzyme and its significance in the possible design of fetal isozyme targeted antineoplastic agents.,  21  (11): [PMID:722719] [10.1021/jm00209a009]

Source

Source(1):

• Scientific Literature