ID: ALA447943

Max Phase: Preclinical

Molecular Formula: C14H28N2O4

Molecular Weight: 288.39

Molecule Type: Small molecule

Representations

Synonyms (1): N-Pentylpantothenamide
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO

Standard InChI:  InChI=1S/C14H28N2O4/c1-4-5-6-8-15-11(18)7-9-16-13(20)12(19)14(2,3)10-17/h12,17,19H,4-10H2,1-3H3,(H,15,18)(H,16,20)/t12-/m0/s1

Standard InChI Key:  HWNKKPMQPCHGBA-LBPRGKRZSA-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: 288.39

Molecular Weight (Monoisotopic): 288.2049

AlogP: 0.18

#Rotatable Bonds: 10

Polar Surface Area: 98.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.69

CX Basic pKa:

CX LogP: -0.17

CX LogD: -0.17

Aromatic Rings: 0

Heavy Atoms: 20

QED Weighted: 0.43

Np Likeness Score: -0.03

References

1. Mercer AC, Meier JL, Hur GH, Smith AR, Burkart MD..  (2008)  Antibiotic evaluation and in vivo analysis of alkynyl Coenzyme A antimetabolites in Escherichia coli.,  18  (22): [PMID:18701278] [10.1016/j.bmcl.2008.07.078]

2. Thomas J, Cronan JE..  (2010)  Antibacterial activity of N-pentylpantothenamide is due to inhibition of coenzyme a synthesis.,  54  (3): [PMID:20047918] [10.1128/aac.01473-09]

3. Akinnusi TO, Vong K, Auclair K..  (2011)  Geminal dialkyl derivatives of N-substituted pantothenamides: synthesis and antibacterial activity.,  19  (8): [PMID:21440446] [10.1016/j.bmc.2011.02.053]

4. de Villiers M, Macuamule C, Spry C, Hyun YM, Strauss E, Saliba KJ..  (2013)  Structural modification of pantothenamides counteracts degradation by pantetheinase and improves antiplasmodial activity.,  4  (8): [PMID:24900746] [10.1021/ml400180d]

5. Awuah E, Ma E, Hoegl A, Vong K, Habib E, Auclair K..  (2014)  Exploring structural motifs necessary for substrate binding in the active site of Escherichia coli pantothenate kinase.,  22  (12): [PMID:24814884] [10.1016/j.bmc.2014.04.030]

6. Moreau RJ, Skepper CK, Appleton BA, Blechschmidt A, Balibar CJ, Benton BM, Drumm JE, Feng BY, Geng M, Li C, Lindvall MK, Lingel A, Lu Y, Mamo M, Mergo W, Polyakov V, Smith TM, Takeoka K, Uehara K, Wang L, Wei JR, Weiss AH, Xie L, Xu W, Zhang Q, de Vicente J..  (2018)  Fragment-Based Drug Discovery of Inhibitors of Phosphopantetheine Adenylyltransferase from Gram-Negative Bacteria.,  61  (8): [PMID:29498517] [10.1021/acs.jmedchem.7b01691]

7. Guan J, Barnard L, Cresson J, Hoegl A, Chang JH, Strauss E, Auclair K..  (2018)  Probing the ligand preferences of the three types of bacterial pantothenate kinase.,  26  (22): [PMID:30429095] [10.1016/j.bmc.2018.10.042]

Source

Source(1):

• Scientific Literature