ID: ALA3329237

Max Phase: Preclinical

Molecular Formula: C31H35N7O4

Molecular Weight: 569.67

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(/C(=N/NC(=O)NNC(=O)NCCCC(C)Nc2cc(OC)cc3cccnc23)c2ccccc2)cc1

Standard InChI:  InChI=1S/C31H35N7O4/c1-21(34-27-20-26(42-3)19-24-12-8-17-32-29(24)27)9-7-18-33-30(39)36-38-31(40)37-35-28(22-10-5-4-6-11-22)23-13-15-25(41-2)16-14-23/h4-6,8,10-17,19-21,34H,7,9,18H2,1-3H3,(H2,33,36,39)(H2,37,38,40)/b35-28+

Standard InChI Key:  XKFBGYTWFFMFHI-AWQADKOQSA-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: 569.67

Molecular Weight (Monoisotopic): 569.2751

AlogP: 4.80

#Rotatable Bonds: 11

Polar Surface Area: 138.00

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.88

CX Basic pKa: 4.06

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.10

Np Likeness Score: -0.96

References

1. Pavić K, Perković I, Cindrić M, Pranjić M, Martin-Kleiner I, Kralj M, Schols D, Hadjipavlou-Litina D, Katsori AM, Zorc B..  (2014)  Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: synthesis, cytostatic and antioxidative activity.,  86  [PMID:25203780] [10.1016/j.ejmech.2014.09.013]

2. Levatić J, Pavić K, Perković I, Uzelac L, Ester K, Kralj M, Kaiser M, Rottmann M, Supek F, Zorc B..  (2018)  Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity.,  146  [PMID:29407988] [10.1016/j.ejmech.2018.01.062]

3. Pavić K, Perković I, Pospíšilová Š, Machado M, Fontinha D, Prudêncio M, Jampilek J, Coffey A, Endersen L, Rimac H, Zorc B..  (2018)  Primaquine hybrids as promising antimycobacterial and antimalarial agents.,  143  [PMID:29220797] [10.1016/j.ejmech.2017.11.083]

Source

Source(1):

• Scientific Literature