Thaxtomin C

ID: ALA2270641

Cas Number: 140111-05-3

PubChem CID: 11101250

Product Number: T344154, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H20N4O4

Molecular Weight: 392.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]1Cc1c[nH]c2cccc([N+](=O)[O-])c12

Standard InChI:  InChI=1S/C21H20N4O4/c1-24-18(11-14-12-22-15-8-5-9-17(19(14)15)25(28)29)20(26)23-16(21(24)27)10-13-6-3-2-4-7-13/h2-9,12,16,18,22H,10-11H2,1H3,(H,23,26)/t16-,18-/m0/s1

Standard InChI Key:  IAIWBAHUWORDTI-WMZOPIPTSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   16.3383   -4.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3371   -5.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0452   -5.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0434   -4.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7520   -4.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7523   -5.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5309   -5.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0120   -5.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5305   -4.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0394   -3.4444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3305   -3.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7459   -3.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7828   -3.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5820   -3.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1286   -4.0855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9248   -3.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1811   -3.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6350   -2.5325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8324   -2.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2866   -2.0915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4695   -4.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8948   -2.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9065   -1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6230   -1.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6364   -0.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9336   -0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2169   -0.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2083   -1.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8732   -4.8617    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
 15 29  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270641

   Thaxtomin 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: 392.42

Molecular Weight (Monoisotopic): 392.1485

AlogP: 2.19

#Rotatable Bonds: 5

Polar Surface Area: 108.34

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: 0.45

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