2-[(2,6-Dimethyl-phenyl)-(2-methoxy-acetyl)-amino]-propionic acid methyl ester

ID: ALA105809

Cas Number: 57837-19-1

PubChem CID: 42586

Product Number: M110059, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H21NO4

Molecular Weight: 279.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Metalaxyl | METALAXYL|57837-19-1|Ridomil|Allegiance|Metalaxil|Metanaxin|Metasyl|Metaxanin|Apron|Jiashuangling|Ridomil 72WP|Subdue|Ridomil Vino|Apron FL|Apron SD 35|IPO-FS|Methyl 2-(N-(2,6-dimethylphenyl)-2-methoxyacetamido)propanoate|(+/-)-Metalaxyl|L-Metalaxyl|CG 117|CGA 48988|DL-Alanine, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-, methyl ester|CGA-48988|DTXSID6024175|CHEBI:82790|methyl 2-(N-(2-methoxyacetyl)-2,6-dimethylanilino)propanoate|Methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaniShow More⌵

Canonical SMILES:  COCC(=O)N(c1c(C)cccc1C)C(C)C(=O)OC

Standard InChI:  InChI=1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3

Standard InChI Key:  ZQEIXNIJLIKNTD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    5.9500   -6.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -7.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -6.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -8.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250   -6.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -8.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875   -6.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -4.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875   -6.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1125   -7.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -8.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -7.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250   -8.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250   -6.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -8.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  6  2  2  0
  7  2  1  0
  8  3  2  0
  9  5  2  0
 10  5  1  0
 11  3  1  0
 12  4  1  0
 13 11  1  0
 14 15  1  0
 15  7  2  0
 16  6  1  0
 17  7  1  0
 18  6  1  0
 19 10  1  0
 20 13  1  0
 14 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA105809

   Metalaxyl solution

Molecule Features

Natural Product: Yes

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

Calculated Properties

Molecular Weight: 279.34

Molecular Weight (Monoisotopic): 279.1471

AlogP: 1.84

#Rotatable Bonds: 5

Polar Surface Area: 55.84

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.12

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.77

Np Likeness Score: -0.47

References

1. Lidert Z, Young DH, Bowers-Daines MM, Sherba SE, Mehta RJ, Lange BC, Swithenbank C, Kiyokawa H, Johnson MG, Morris-Natschke SL, Lee K.  (1997)  1,4-Bis-(2,3-epoxypropylamino)-9,10-anthracenedione and related compounds as potent antifungal and antimicrobial agents,  7  (24): [10.1016/S0960-894X(97)10176-7]

2. Lee JY, Moon SS, Yun BS, Yoo ID, Hwang BK..  (2004)  Thiobutacin, a novel antifungal and antioomycete antibiotic from Lechevalieria aerocolonigenes.,  67  (12): [PMID:15620255] [10.1021/np049786v]

3. 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]

4. Pushpalatha HG, Mythrashree SR, Shetty R, Geetha NP, Sharathchandra RG, Amruthesh KN, Shetty HS..  (2007)  Ability of vitamins to induce downy mildew disease resistance and growth promotion in pearl millet,  26  (11): [10.1016/j.cropro.2007.02.012]

5. Chattapadhyay TK, Dureja P..  (2006)  Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones.,  54  (6): [PMID:16536586] [10.1021/jf052792s]

6. Park HJ, Lee JY, Hwang IS, Yun BS, Kim BS, Hwang BK..  (2006)  Isolation and antifungal and antioomycete activities of staurosporine from Streptomyces roseoflavus strain LS-A24.,  54  (8): [PMID:16608228] [10.1021/jf0532617]

7. Kim BS, Moon SS, Hwang BK..  (2000)  Structure elucidation and antifungal activity of an anthracycline antibiotic, daunomycin, isolated from Actinomadura roseola.,  48  (5): [PMID:10820108] [10.1021/jf990402u]

8. Abdel-Aty AS.  (2010)  Fungicidal activity of indole derivatives against some plant pathogenic fungi,  35  (4): [10.1584/jpestics.G09-66]

9. Angioni A, Barra A, Arlorio M, Coisson JD, Russo MT, Pirisi FM, Satta M, Cabras P..  (2003)  Chemical composition, plant genetic differences, and antifungal activity of the essential oil of Helichrysum italicum G. Don ssp. microphyllum (Willd) Nym.,  51  (4): [PMID:12568568] [10.1021/jf025940c]

10. Dan Y, Liu HY, Gao WW, Chen SL..  (2010)  Activities of essential oils from Asarum heterotropoides var. mandshuricum against five phytopathogens,  29  (3): [10.1016/j.cropro.2009.12.007]

11. Miyake Y, Sakai J, Shibata M, Yonekura N, Miura I, Kumakura K, Nagayama K.  (2005)  Fungicidial Activity of Benthiavalicarb-isopropyl against Phytophthora infestans and Its Controlling Activity against Late Blight Diseases,  30  (4): [10.1584/jpestics.30.390]

12. Amponsah NT, Jones E, Ridgway HJ, Jaspers MV..  (2012)  Evaluation of fungicides for the management of Botryosphaeria dieback diseases of grapevines.,  68  (5): [PMID:22290833] [10.1002/ps.2309]

13. PubChem BioAssay data set, 

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

17. PubChem BioAssay data set, 

18. Dai JK, Dan WJ, Wan JB..  (2022)  Natural and synthetic β-carboline as a privileged antifungal scaffolds.,  229  [PMID:34954591] [10.1016/j.ejmech.2021.114057]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays