4-(3-{4-[amino(imino)methyl]phenyl}triaz-1-enyl)benzenecarboximidamide; (acetylamino)acetic acid

ID: ALA124025

Chembl Id: CHEMBL124025

Cas Number: 15114-96-2

PubChem CID: 65060

Max Phase: Preclinical

Molecular Formula: C18H22N8O3

Molecular Weight: 281.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Diminazene Aceturate | Diaminazene aceturate|Azidine|Ganasag|Ganaseg|berenil|Diminazine aceturate|Beronal|Azidin|Diminazene monoaceturate|Bevenil|M011GS5PF5|UNII-M011GS5PF5|p,p'-Diguanyldiazoaminobenzene diaceturate|4,4'-(Diazoamino)dibenzamidine diaceturate|4,4'-Diamidinodiazoaminobenzene diaceturate|1,3-Bis(4-guanylphenyl)triazene diaceturate|1,3-Bis(p-amidinophenyl)triazene bis(N-acetylglycinate)|15114-96-2|JI8SAD85NO|Di-(4-amidinophenyl)-triazine-(N-1,3)-diaceturate|Diminazenaceturate|bis(2-Show More⌵

Canonical SMILES:  CC(=O)NCC(=O)O.N=C(N)c1ccc(/N=N/Nc2ccc(C(=N)N)cc2)cc1

Standard InChI:  InChI=1S/C14H15N7.C4H7NO3/c15-13(16)9-1-5-11(6-2-9)19-21-20-12-7-3-10(4-8-12)14(17)18;1-3(6)5-2-4(7)8/h1-8H,(H3,15,16)(H3,17,18)(H,19,20);2H2,1H3,(H,5,6)(H,7,8)

Standard InChI Key:  XJLITJHUQRBWPN-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

Calculated Properties

Molecular Weight: 281.32

Molecular Weight (Monoisotopic): 281.1389

AlogP: 2.37

#Rotatable Bonds: 5

Polar Surface Area: 136.49

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 12.07

CX LogP: 1.76

CX LogD: -3.04

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.25

Np Likeness Score: -0.47

References

1. Antonini I, Polucci P, Jenkins TC, Kelland LR, Menta E, Pescalli N, Stefanska B, Mazerski J, Martelli S..  (1997)  1-[(omega-aminoalkyl)amino]-4-[N-(omega-aminoalkyl)carbamoyl]-9-oxo-9, 10-dihydroacridines as intercalating cytotoxic agents: synthesis, DNA binding, and biological evaluation.,  40  (23): [PMID:9371240] [10.1021/jm970114u]

2. Ulrich P, Cerami A..  (1984)  Trypanocidal 1,3-arylene diketone bis(guanylhydrazone)s. Structure-activity relationships among substituted and heterocyclic analogues.,  27  (1): [PMID:6690682] [10.1021/jm00367a007]

3. Subeki, Matsuura H, Takahashi K, Nabeta K, Yamasaki M, Maede Y, Katakura K..  (2007)  Screening of Indonesian medicinal plant extracts for antibabesial activity and isolation of new quassinoids from Brucea javanica.,  70  (10): [PMID:17896817] [10.1021/np070236h]

4. Subeki S, Matsuura H, Takahashi K, Yamasaki M, Yamato O, Maede Y, Katakura K, Kobayashi S, Trimurningsih T, Chairul C, Yoshihara T..  (2005)  Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri.,  68  (4): [PMID:15844943] [10.1021/np0497245]

5. Changtam C, de Koning HP, Ibrahim H, Sajid MS, Gould MK, Suksamrarn A..  (2010)  Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.,  45  (3): [PMID:20004045] [10.1016/j.ejmech.2009.11.035]

6. Nakaminami H, Noguchi N, Sasatsu M..  (2010)  Fluoroquinolone efflux by the plasmid-mediated multidrug efflux pump QacB variant QacBIII in Staphylococcus aureus.,  54  (10): [PMID:20660673] [10.1128/aac.01065-09]

7. Cimbora-Zovko T, Brozovic A, Piantanida I, Fritz G, Virag A, Alič B, Majce V, Kočevar M, Polanc S, Osmak M..  (2011)  Synthesis and biological evaluation of 4-nitro-substituted 1,3-diaryltriazenes as a novel class of potent antitumor agents.,  46  (7): [PMID:21550697] [10.1016/j.ejmech.2011.04.024]

8. Rodenko B, Al-Salabi MI, Teka IA, Ho W, El-Sabbagh N, Ali JA, Ibrahim HM, Wanner MJ, Koomen GJ, de Koning HP..  (2011)  Synthesis of marine-derived 3-alkylpyridinium alkaloids with potent antiprotozoal activity.,  2  (12): [PMID:24900279] [10.1021/ml200160k]

9. Li L, Chenna BC, Yang KS, Cole TR, Goodall ZT, Giardini M, Moghadamchargari Z, Hernandez EA, Gomez J, Calvet CM, Bernatchez JA, Mellott DM, Zhu J, Rademacher A, Thomas D, Blankenship LR, Drelich A, Laganowsky A, Tseng CK, Liu WR, Wand AJ, Cruz-Reyes J, Siqueira-Neto JL, Meek TD..  (2021)  Self-Masked Aldehyde Inhibitors: A Novel Strategy for Inhibiting Cysteine Proteases.,  64  (15.0): [PMID:34288674] [10.1021/acs.jmedchem.1c00628]

Source

Source(1):

• Scientific Literature