ID: ALA70590

Max Phase: Preclinical

Molecular Formula: C28H43NO6

Molecular Weight: 489.65

Molecule Type: Small molecule

Representations

Synonyms (1): Borrelidin
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@@H]1C[C@H](C)C[C@H](C)[C@@H](O)CC(=O)O[C@H]([C@@H]2CCC[C@H]2C(=O)O)C/C=C/C=C(/C#N)[C@H](O)[C@@H](C)C1

Standard InChI:  InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1

Standard InChI Key:  OJCKRNPLOZHAOU-UGKRXNSESA-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: 489.65

Molecular Weight (Monoisotopic): 489.3090

AlogP: 4.64

#Rotatable Bonds: 2

Polar Surface Area: 127.85

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.87

CX Basic pKa:

CX LogP: 4.66

CX LogD: 1.43

Aromatic Rings: 0

Heavy Atoms: 35

QED Weighted: 0.48

Np Likeness Score: 1.43

References

1. Eastwood EL, Schaus SE..  (2003)  Borrelidin induces the transcription of amino acid biosynthetic enzymes via a GCN4-dependent pathway.,  13  (13): [PMID:12798341] [10.1016/s0960-894x(03)00406-2]

2. Wilkinson B, Gregory MA, Moss SJ, Carletti I, Sheridan RM, Kaja A, Ward M, Olano C, Mendez C, Salas JA, Leadlay PF, vanGinckel R, Zhang MQ..  (2006)  Separation of anti-angiogenic and cytotoxic activities of borrelidin by modification at the C17 side chain.,  16  (22): [PMID:16962775] [10.1016/j.bmcl.2006.08.073]

3. Gutierrez-Lugo MT, Bewley CA..  (2011)  Susceptibility and mode of binding of the Mycobacterium tuberculosis cysteinyl transferase mycothiol ligase to tRNA synthetase inhibitors.,  21  (8): [PMID:21392992] [10.1016/j.bmcl.2011.02.042]

4. Liu CX, Zhang J, Wang XJ, Qian PT, Wang JD, Gao YM, Yan YJ, Zhang SZ, Xu PF, Li WB, Xiang WS..  (2012)  Antifungal activity of borrelidin produced by a Streptomyces strain isolated from soybean.,  60  (5): [PMID:22242825] [10.1021/jf2044982]

5. Gao YM, Wang XJ, Zhang J, Li M, Liu CX, An J, Jiang L, Xiang WS..  (2012)  Borrelidin, a potent antifungal agent: insight into the antifungal mechanism against Phytophthora sojae.,  60  (39): [PMID:22967236] [10.1021/jf302857x]

6. Sugawara A, Tanaka T, Hirose T, Ishiyama A, Iwatsuki M, Takahashi Y, Otoguro K, Ōmura S, Sunazuka T..  (2013)  Borrelidin analogues with antimalarial activity: design, synthesis and biological evaluation against Plasmodium falciparum parasites.,  23  (8): [PMID:23499502] [10.1016/j.bmcl.2013.02.075]

7. Schulze CJ, Bray WM, Loganzo F, Lam MH, Szal T, Villalobos A, Koehn FE, Linington RG..  (2014)  Borrelidin B: isolation, biological activity, and implications for nitrile biosynthesis.,  77  (11): [PMID:25393949] [10.1021/np500727g]

8. Sidhu A, Miller JR, Tripathi A, Garshott DM, Brownell AL, Chiego DJ, Arevang C, Zeng Q, Jackson LC, Bechler SA, Callaghan MU, Yoo GH, Sethi S, Lin HS, Callaghan JH, Tamayo-Castillo G, Sherman DH, Kaufman RJ, Fribley AM..  (2015)  Borrelidin Induces the Unfolded Protein Response in Oral Cancer Cells and Chop-Dependent Apoptosis.,  6  (11): [PMID:26617965] [10.1021/acsmedchemlett.5b00133]

9.  (2016)  7  (8): [10.1039/C6MD00274A]

10. Hu C, Su H, Luo J, Han L, Liu Q, Wu W, Mu Y, Guan P, Sun T, Huang X..  (2018)  Design, synthesis and antifungal evaluation of borrelidin derivatives.,  26  (23-24): [PMID:30442507] [10.1016/j.bmc.2018.11.005]

Source

Source(1):

• Scientific Literature