ID: ALA313478

Max Phase: Preclinical

Molecular Formula: C9H9N5O

Molecular Weight: 203.21

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ncnc2c1ncn2C=C=CCO

Standard InChI:  InChI=1S/C9H9N5O/c10-8-7-9(12-5-11-8)14(6-13-7)3-1-2-4-15/h2-3,5-6,15H,4H2,(H2,10,11,12)

Standard InChI Key:  TYQIYCWCVLIXPH-UHFFFAOYSA-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: 203.21

Molecular Weight (Monoisotopic): 203.0807

AlogP: 0.03

#Rotatable Bonds: 2

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 3.40

CX LogP: -0.46

CX LogD: -0.46

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.67

Np Likeness Score: 0.34

References

1. Legraverend M, Boumchita H, Zerial A, Huel C, Lemaitre M, Bisagni E..  (1990)  Synthesis of new (+-)-3,5-dihydroxypentyl nucleoside analogues from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation.,  33  (9): [PMID:2391689] [10.1021/jm00171a022]

2. Egron D, Périgaud C, Gosselin G, Aubertin AM, Gatanaga H, Mitsuya H, Zemlicka J, Imbach JL..  (2002)  Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.,  12  (2): [PMID:11755368] [10.1016/s0960-894x(01)00728-4]

3. Winter H, Maeda Y, Mitsuya H, Zemlicka J..  (1996)  Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.,  39  (17): [PMID:8765513] [10.1021/jm960330n]

4. Winter H, Maeda Y, Mitsuya H, Zemlicka J..  (1996)  Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.,  39  (17): [PMID:8765513] [10.1021/jm960330n]

5. Megati S, Goren Z, Silverton JV, Orlina J, Nishimura H, Shirasaki T, Mitsuya H, Zemlicka J..  (1992)  (R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.,  35  (22): [PMID:1304169] [10.1021/jm00100a016]

6. Megati S, Goren Z, Silverton JV, Orlina J, Nishimura H, Shirasaki T, Mitsuya H, Zemlicka J..  (1992)  (R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.,  35  (22): [PMID:1304169] [10.1021/jm00100a016]

7. Megati S, Goren Z, Silverton JV, Orlina J, Nishimura H, Shirasaki T, Mitsuya H, Zemlicka J..  (1992)  (R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.,  35  (22): [PMID:1304169] [10.1021/jm00100a016]

8. Phadtare S, Kessel D, Corbett TH, Renis HE, Court BA, Zimlicka J..  (1991)  Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.,  34  (1): [PMID:1992143] [10.1021/jm00105a064]

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Diversity Set V,  [10.6019/CHEMBL4296182]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data