1-(but-2-enyl)-3-(8-(4-imino-2-oxo-1,3,5-triazacyclotridecan-1-yl)octyl)guanidine

ID: ALA575667

Chembl Id: CHEMBL575667

PubChem CID: 44203963

Max Phase: Preclinical

Molecular Formula: C23H45N7O

Molecular Weight: 435.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C/CNC(=N)NCCCCCCCCN1CCCCCCCCNC(=N)NC1=O

Standard InChI:  InChI=1S/C23H45N7O/c1-2-3-16-26-21(24)27-17-12-8-4-6-10-14-19-30-20-15-11-7-5-9-13-18-28-22(25)29-23(30)31/h2-3H,4-20H2,1H3,(H3,24,26,27)(H3,25,28,29,31)/b3-2+

Standard InChI Key:  MQSMYZIWVVXCPW-NSCUHMNNSA-N

Alternative Forms

1. Parent:

   

   ALA575667

   1-[(E)-but-2-enyl]-3-[8-(4-imino-2-oxo-1,3,5-triazacyclotridec-1-yl)octyl]guanidine

2. Alternative Forms:

   

   ALA575667

   ---

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: 435.66

Molecular Weight (Monoisotopic): 435.3686

AlogP: 3.91

#Rotatable Bonds: 11

Polar Surface Area: 116.13

Molecular Species: BASE

HBA: 3

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.31

CX Basic pKa: 12.39

CX LogP: 3.49

CX LogD: 1.41

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.13

Np Likeness Score: 0.13

References

1. Manetti F, Castagnolo D, Raffi F, Zizzari AT, Rajamäki S, D'Arezzo S, Visca P, Cona A, Fracasso ME, Doria D, Posteraro B, Sanguinetti M, Fadda G, Botta M..  (2009)  Synthesis of new linear guanidines and macrocyclic amidinourea derivatives endowed with high antifungal activity against Candida spp. and Aspergillus spp.,  52  (23): [PMID:19650630] [10.1021/jm900760k]

2. Sanguinetti M, Sanfilippo S, Castagnolo D, Sanglard D, Posteraro B, Donzellini G, Botta M..  (2013)  Novel Macrocyclic Amidinoureas: Potent Non-Azole Antifungals Active against Wild-Type and Resistant Candida Species.,  4  (9): [PMID:24900759] [10.1021/ml400187w]

3. Deodato D, Maccari G, De Luca F, Sanfilippo S, Casian A, Martini R, D'Arezzo S, Bonchi C, Bugli F, Posteraro B, Vandeputte P, Sanglard D, Docquier JD, Sanguinetti M, Visca P, Botta M..  (2016)  Biological Characterization and in Vivo Assessment of the Activity of a New Synthetic Macrocyclic Antifungal Compound.,  59  (8): [PMID:27045868] [10.1021/acs.jmedchem.6b00018]

4. Maccari G, Deodato D, Fiorucci D, Orofino F, Truglio GI, Pasero C, Martini R, De Luca F, Docquier JD, Botta M..  (2017)  Design and synthesis of a novel inhibitor of T. Viride chitinase through an in silico target fishing protocol.,  27  (15): [PMID:28610983] [10.1016/j.bmcl.2017.06.016]

5. Balestri LJI, Trivisani CI, Orofino F, Fiorucci D, Truglio GI, D'Agostino I, Poggialini F, Botta L, Docquier JD, Dreassi E..  (2023)  Discovery and Optimization of a Novel Macrocyclic Amidinourea Series Active as Acidic Mammalian Chitinase Inhibitors.,  14  (4): [PMID:37077400] [10.1021/acsmedchemlett.2c00472]

Source

Source(1):

• Scientific Literature