Des-N-methylthaxtomin C

ID: ALA2270635

PubChem CID: 76334137

Max Phase: Preclinical

Molecular Formula: C20H18N4O4

Molecular Weight: 378.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@@H](Cc2c[nH]c3cccc([N+](=O)[O-])c23)C(=O)N[C@H]1Cc1ccccc1

Standard InChI:  InChI=1S/C20H18N4O4/c25-19-15(9-12-5-2-1-3-6-12)22-20(26)16(23-19)10-13-11-21-14-7-4-8-17(18(13)14)24(27)28/h1-8,11,15-16,21H,9-10H2,(H,22,26)(H,23,25)/t15-,16-/m0/s1

Standard InChI Key:  NBRLIEDDTJSMAU-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   17.1679  -11.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1667  -12.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8748  -12.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8730  -11.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5816  -11.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5819  -12.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3605  -12.6694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8415  -12.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3601  -11.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8690  -10.3699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1601   -9.9634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5755   -9.9592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6123  -10.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4116  -10.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9581  -11.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7543  -10.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0107  -10.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4645   -9.4580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6620   -9.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1162   -9.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2991  -11.4526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7244   -9.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7360   -8.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4526   -8.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4660   -7.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7632   -7.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0465   -7.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0379   -8.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 10 12  1  0
  4 10  1  0
  9 13  1  0
 14 13  1  1
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16 21  2  0
 17 22  1  1
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270635

   DES-N-METHYLTHAXTOMIN C

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

Calculated Properties

Molecular Weight: 378.39

Molecular Weight (Monoisotopic): 378.1328

AlogP: 1.84

#Rotatable Bonds: 5

Polar Surface Area: 117.13

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.61

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 0.12

References

1. King RR, Lawrence CH, Gray JA..  (2001)  Herbicidal properties of the thaxtomin group of phytotoxins.,  49  (5): [PMID:11368592] [10.1021/jf0012998]

Source

Source(1):

• Scientific Literature