Thaxtomin A, Cellulose synthesis inhibitor

Key facts

CAS number

122380-18-1

Purity

>98%

Form

Solid

form

Source

Streptomyces bottropensis

Molecular weight

438.4 Da

Molecular formula

C₂₂H₂₂N₄O₆

PubChem

180098

Nature

Native

Solubility

Soluble in ethanol

Soluble in DMSO

Biochemical name

Thaxtomin A

Biological description

Phytotoxin and potent necrotic agent. Cellulose synthesis inhibitor. Bacterial NOS metabolite. Inhibits cellulose synthesis in expanding plant tissues. Herbicidal effects in vivo.

Canonical smiles

CN1C(C(=O)N(C(C1=O)(CC2=CC(=CC=C2)O)O)C)CC3=CNC4=C3C(=CC=C4)[N+](=O)[O-]

Isomeric smiles

CN1[C@H](C(=O)N([C@](C1=O)(CC2=CC(=CC=C2)O)O)C)CC3=CNC4=C3C(=CC=C4)[N+](=O)[O-]

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

InChiKey

QRDNJYNIEGRRKV-PGRDOPGGSA-N

IUPAC Name

(3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione