Thaxtomin A

ID: ALA2270642

Cas Number: 122380-18-1

PubChem CID: 180098

Product Number: T276425, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H22N4O6

Molecular Weight: 438.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)[C@](O)(Cc2cccc(O)c2)N(C)C(=O)[C@@H]1Cc1c[nH]c2cccc([N+](=O)[O-])c12

Standard InChI:  InChI=1S/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22+/m0/s1

Standard InChI Key:  QRDNJYNIEGRRKV-PGRDOPGGSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    0.6589   -5.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -6.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3658   -6.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3641   -4.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -5.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729   -6.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516   -6.2681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3326   -5.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8512   -4.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601   -3.9685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512   -3.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666   -3.5578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -4.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027   -3.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -4.6096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   -4.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018   -3.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9556   -3.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -3.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073   -2.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7901   -5.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155   -3.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2271   -2.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9437   -2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9571   -1.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5376   -1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5290   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -4.2428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1938   -5.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -2.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6713   -0.8427    0.0000 O   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  0
 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
 17 29  1  6
 15 30  1  0
 18 31  1  0
 25 32  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270642

   Thaxtomin A

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: 438.44

Molecular Weight (Monoisotopic): 438.1539

AlogP: 1.55

#Rotatable Bonds: 5

Polar Surface Area: 140.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.44

CX Basic pKa: ┄

CX LogP: 2.16

CX LogD: 2.15

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: 0.43

References

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

2. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Gene Expression Atlas Compounds