ID: ALA462018

Max Phase: Phase

Molecular Formula: C13H17N6O7P

Molecular Weight: 400.29

Molecule Type: Small molecule

Representations

Synonyms (5): Phosphate salt of tricyclic nucleoside | Triciribine phosphate | Vqd-002 | NSC-154020 | NSC-280594
Synonyms from Alternative Forms(5):

Canonical SMILES:  CN1N=C(N)c2cn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c3ncnc1c23

Standard InChI:  InChI=1S/C13H17N6O7P/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(21)8(20)6(26-13)3-25-27(22,23)24/h2,4,6,8-9,13,20-21H,3H2,1H3,(H2,14,17)(H2,22,23,24)/t6-,8-,9-,13-/m1/s1

Standard InChI Key:  URLYINUFLXOMHP-HTVVRFAVSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 400.29

Molecular Weight (Monoisotopic): 400.0896

AlogP: -1.77

#Rotatable Bonds: 4

Polar Surface Area: 188.78

Molecular Species: ZWITTERION

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.22

CX Basic pKa: 9.33

CX LogP: -3.78

CX LogD: -4.94

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: 0.62

References

1. Porcari AR, Ptak RG, Borysko KZ, Breitenbach JM, Vittori S, Wotring LL, Drach JC, Townsend LB..  (2000)  Deoxy sugar analogues of triciribine: correlation of antiviral and antiproliferative activity with intracellular phosphorylation.,  43  (12): [PMID:10882371] [10.1021/jm990205m]

2. Porcari AR, Ptak RG, Borysko KZ, Breitenbach JM, Drach JC, Townsend LB..  (2000)  6-N-Acyltriciribine analogues: structure-activity relationship between acyl carbon chain length and activity against HIV-1.,  43  (12): [PMID:10882373] [10.1021/jm990236h]

3. 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]

4. Murakami E, Bao H, Mosley RT, Du J, Sofia MJ, Furman PA..  (2011)  Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.,  54  (16): [PMID:21755941] [10.1021/jm200650j]

5. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

6. Unpublished dataset, 

7. Patel RV, Park SW..  (2015)  Pyrroloaryls and pyrroloheteroaryls: Inhibitors of the HIV fusion/attachment, reverse transcriptase and integrase.,  23  (17): [PMID:26116177] [10.1016/j.bmc.2015.06.016]

8. Klaeger S, Heinzlmeir S and Wilhelm M et al.  (2017)  The target landscape of clinical kinase drugs.,  358  (6367): [PMID:29191878] [10.1126/science.aan4368]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• Kuster lab chemical proteomics drug profiling