ID: ALA400768

Max Phase: Preclinical

Molecular Formula: C19H21N3O2

Molecular Weight: 323.40

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=CC(C)(C)c1[nH]c2ccccc2c1/C=C1\NC(=O)[C@H](C)NC1=O

Standard InChI:  InChI=1S/C19H21N3O2/c1-5-19(3,4)16-13(12-8-6-7-9-14(12)21-16)10-15-18(24)20-11(2)17(23)22-15/h5-11,21H,1H2,2-4H3,(H,20,24)(H,22,23)/b15-10-/t11-/m0/s1

Standard InChI Key:  MYRPIYZIAHOECW-SAIXKJTDSA-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: 323.40

Molecular Weight (Monoisotopic): 323.1634

AlogP: 2.61

#Rotatable Bonds: 3

Polar Surface Area: 73.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.58

CX Basic pKa:

CX LogP: 2.19

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.60

Np Likeness Score: 1.60

References

1. Wang WL, Lu ZY, Tao HW, Zhu TJ, Fang YC, Gu QQ, Zhu WM..  (2007)  Isoechinulin-type alkaloids, variecolorins A-L, from halotolerant Aspergillus variecolor.,  70  (10): [PMID:17896816] [10.1021/np070208z]

2. Pettit GR, Hogan F, Xu JP, Tan R, Nogawa T, Cichacz Z, Pettit RK, Du J, Ye QH, Cragg GM, Herald CL, Hoard MS, Goswami A, Searcy J, Tackett L, Doubek DL, Williams L, Hooper JN, Schmidt JM, Chapuis JC, Tackett DN, Craciunescu F..  (2008)  Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,).,  71  (3): [PMID:18327911] [10.1021/np700738k]

3. Ganihigama DU, Sureram S, Sangher S, Hongmanee P, Aree T, Mahidol C, Ruchirawat S, Kittakoop P..  (2015)  Antimycobacterial activity of natural products and synthetic agents: pyrrolodiquinolines and vermelhotin as anti-tubercular leads against clinical multidrug resistant isolates of Mycobacterium tuberculosis.,  89  [PMID:25462220] [10.1016/j.ejmech.2014.10.026]

4. Chen X, Si L, Liu D, Proksch P, Zhang L, Zhou D, Lin W..  (2015)  Neoechinulin B and its analogues as potential entry inhibitors of influenza viruses, targeting viral hemagglutinin.,  93  [PMID:25681711] [10.1016/j.ejmech.2015.02.006]

5. Meng LH, Du FY, Li XM, Pedpradab P, Xu GM, Wang BG..  (2015)  Rubrumazines A-C, Indolediketopiperazines of the Isoechinulin Class from Eurotium rubrum MA-150, a Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.,  78  (4): [PMID:25730346] [10.1021/np5007839]

6. Kamauchi H, Kinoshita K, Sugita T, Koyama K..  (2016)  Conditional changes enhanced production of bioactive metabolites of marine derived fungus Eurotium rubrum.,  26  (20): [PMID:27641468] [10.1016/j.bmcl.2016.09.017]

7. Nishiuchi K, Ohashi H, Nishioka K, Yamasaki M, Furuta M, Mashiko T, Tomoshige S, Ohgane K, Kamisuki S, Watashi K, Kuramochi K..  (2022)  Synthesis and Antiviral Activities of Neoechinulin B and Its Derivatives.,  85  (1.0): [PMID:34967639] [10.1021/acs.jnatprod.1c01120]

Source

Source(1):

• Scientific Literature