ID: ALA6269

Max Phase: Preclinical

Molecular Formula: C33H52N6O4

Molecular Weight: 596.82

Molecule Type: Small molecule

Representations

Synonyms (1): SC-58272
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1nccn1CCCCc1ccc(CC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)NCCC2CCCCC2)cc1

Standard InChI:  InChI=1S/C33H52N6O4/c1-25-35-20-22-39(25)21-8-6-11-27-13-15-28(16-14-27)23-31(41)37-30(24-40)33(43)38-29(12-5-7-18-34)32(42)36-19-17-26-9-3-2-4-10-26/h13-16,20,22,26,29-30,40H,2-12,17-19,21,23-24,34H2,1H3,(H,36,42)(H,37,41)(H,38,43)/t29-,30-/m0/s1

Standard InChI Key:  WHLPIOSHBKQGHA-KYJUHHDHSA-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: 596.82

Molecular Weight (Monoisotopic): 596.4050

AlogP: 2.93

#Rotatable Bonds: 19

Polar Surface Area: 151.37

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.20

CX Basic pKa: 10.20

CX LogP: 2.39

CX LogD: -0.38

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: -0.45

References

1. Devadas B, Freeman SK, McWherter CA, Kishore NS, Lodge JK, Jackson-Machelski E, Gordon JI, Sikorski JA..  (1998)  Novel biologically active nonpeptidic inhibitors of myristoylCoA:protein N-myristoyltransferase.,  41  (6): [PMID:9526574] [10.1021/jm980001q]

2. Masubuchi M, Kawasaki K, Ebiike H, Ikeda Y, Tsujii S, Sogabe S, Fujii T, Sakata K, Shiratori Y, Aoki Y, Ohtsuka T, Shimma N..  (2001)  Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1.,  11  (14): [PMID:11459642] [10.1016/s0960-894x(01)00319-5]

3. Devadas B, Zupec ME, Freeman SK, Brown DL, Nagarajan S, Sikorski JA, McWherter CA, Getman DP, Gordon JI..  (1995)  Design and syntheses of potent and selective dipeptide inhibitors of Candida albicans myristoyl-CoA:protein N-myristoyltransferase.,  38  (11): [PMID:7783114] [10.1021/jm00011a001]

4. Devadas B, Freeman SK, McWherter CA, Kuneman DW, Vinjamoori DV, Sikorski JA.  (1996)  A chiral recognition element with an unusual size constraint affects the potency and selectivity for peptidomimetic inhibitors of Candida albicans myristoyl-CoA:protein N-myristoyltransferase,  6  (16): [10.1016/0960-894X(96)00354-X]

5. Devadas B, Freeman SK, Zupec ME, Lu HF, Nagarajan SR, Kishore NS, Lodge JK, Kuneman DW, McWherter CA, Vinjamoori DV, Getman DP, Gordon JI, Sikorski JA..  (1997)  Design and synthesis of novel imidazole-substituted dipeptide amides as potent and selective inhibitors of Candida albicans myristoylCoA:protein N-myristoyltransferase and identification of related tripeptide inhibitors with mechanism-based antifungal activity.,  40  (16): [PMID:9258368] [10.1021/jm970094w]

6. Brown DL, Devadas B, Lu H, Nagarajan S, Zupec ME, Freeman SK, McWherter CA, Getman DP, Sikorski JA.  (1997)  Replacements for lysine in l-seryl-l-lysyl dipeptide amide inhibitors of candida albicans myristoyl-CoA:protein N-myristoyltransferase,  7  (3): [10.1016/S0960-894X(97)00030-9]

7. Wu J, Tao Y, Zhang M, Howard MH, Gutteridge S, Ding J..  (2007)  Crystal structures of Saccharomyces cerevisiae N-myristoyltransferase with bound myristoyl-CoA and inhibitors reveal the functional roles of the N-terminal region.,  282  (30): [PMID:17513302] [10.1074/jbc.m702696200]

Source

Source(1):

• Scientific Literature