ID: ALA488625

Max Phase: Preclinical

Molecular Formula: C9H12N6O4

Molecular Weight: 268.23

Molecule Type: Small molecule

Representations

Synonyms (1): Cytarazid
Synonyms from Alternative Forms(1):

Canonical SMILES:  [N-]=[N+]=N[C@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(N)nc1=O

Standard InChI:  InChI=1S/C9H12N6O4/c10-5-1-2-15(9(18)12-5)8-6(13-14-11)7(17)4(3-16)19-8/h1-2,4,6-8,16-17H,3H2,(H2,10,12,18)/t4-,6+,7-,8-/m1/s1

Standard InChI Key:  FEOYKPQEERVCAV-PXBUCIJWSA-N

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

Properties

Molecular Weight: 268.23

Molecular Weight (Monoisotopic): 268.0920

AlogP: -1.25

#Rotatable Bonds: 3

Polar Surface Area: 159.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.14

CX Basic pKa:

CX LogP: -1.98

CX LogD: -2.09

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.35

Np Likeness Score: 1.43

References

1. Matsuda A, Yasuoka J, Sasaki T, Ueda T..  (1991)  Nucleosides and nucleotides. 95. Improved synthesis of 1-(2-azido-2-deoxy-beta-D-arabinofuranosyl)cytosine (cytarazid) and -thymine. Inhibitory spectrum of cytarazid on the growth of various human tumor cells in vitro.,  34  (3): [PMID:2002478] [10.1021/jm00107a018]

2. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

3. Bobek M, Cheng YC, Bloch A..  (1978)  Novel arabinofuranosyl derivatives of cytosine resistant to enzymatic deamination and possessing potent antitumor activity.,  21  (7): [PMID:276611] [10.1021/jm00205a001]

Source

Source(1):

• Scientific Literature