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122380-18-1 | 2,5-Piperazinedione, 3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-, (3R,6S)-
CAS No: 122380-18-1 Catalog No: AG00176P MDL No:
Product Description
Catalog Number:
AG00176P
Chemical Name:
2,5-Piperazinedione, 3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-, (3R,6S)-
CAS Number:
122380-18-1
Molecular Formula:
C22H22N4O6
Molecular Weight:
438.4333
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
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
InChI Key:
QRDNJYNIEGRRKV-PGRDOPGGSA-N
SMILES:
Oc1cccc(c1)C[C@]1(O)N(C)C(=O)[C@@H](N(C1=O)C)Cc1c[nH]c2c1c(ccc2)[N+](=O)[O-]
NSC Number:
630669
Properties
Complexity:
759
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
438.154g/mol
Formal Charge:
0
Heavy Atom Count:
32
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
438.44g/mol
Monoisotopic Mass:
438.154g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
143A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.9
Literature
| Title | Journal |
|---|---|
| Potato suberin induces differentiation and secondary metabolism in the genus Streptomyces. | Microbes and environments 20120301 |
| Tryptophan regulates thaxtomin A and indole-3-acetic acid production in Streptomyces scabiei and modifies its interactions with radish seedlings. | Phytopathology 20110901 |
| The ability of Pseudomonas sp. LBUM 223 to produce phenazine-1-carboxylic acid affects the growth of Streptomyces scabies, the expression of thaxtomin biosynthesis genes and the biological control potential against common scab of potato. | FEMS microbiology ecology 20110101 |
| Involvement of the plant polymer Suberin and the disaccharide cellobiose in triggering thaxtomin A biosynthesis, a phytotoxin produced by the pathogenic agent streptomyces scabies. | Phytopathology 20100101 |
| Habituation to thaxtomin A in hybrid poplar cell suspensions provides enhanced and durable resistance to inhibitors of cellulose synthesis. | BMC plant biology 20100101 |
| Streptomyces scabiei and its toxin thaxtomin A induce scopoletin biosynthesis in tobacco and Arabidopsis thaliana. | Plant cell reports 20091201 |
| 4-Nitrotryptophan is a substrate for the non-ribosomal peptide synthetase TxtB in the thaxtomin A biosynthetic pathway. | Molecular microbiology 20090801 |
| Transcriptional profiling in response to inhibition of cellulose synthesis by thaxtomin A and isoxaben in Arabidopsis thaliana suspension cells. | Plant cell reports 20090501 |
| The thaxtomin phytotoxins: sources, synthesis, biosynthesis, biotransformation and biological activity. | Phytochemistry 20090501 |
| Thaxtomin A affects CESA-complex density, expression of cell wall genes, cell wall composition, and causes ectopic lignification in Arabidopsis thaliana seedlings. | Journal of experimental botany 20090301 |
| Thaxtomin biosynthesis: the path to plant pathogenicity in the genus Streptomyces. | Antonie van Leeuwenhoek 20080601 |
| Effect of carbohydrates on the production of thaxtomin A by Streptomyces acidiscabies. | Archives of microbiology 20070701 |
| Influence of thaxtomins in different combinations and concentrations on growth of micropropagated potato shoot cultures. | Journal of agricultural and food chemistry 20060503 |
| Nitric oxide synthase inhibitors and nitric oxide donors modulate the biosynthesis of thaxtomin A, a nitrated phytotoxin produced by Streptomyces spp. | Nitric oxide : biology and chemistry 20050201 |
| Characterization of Streptomyces scabies mutants deficient in melanin biosynthesis. | Canadian journal of microbiology 20040901 |
| Nitration of a peptide phytotoxin by bacterial nitric oxide synthase. | Nature 20040506 |
| Effect of amino acids on thaxtomin A biosynthesis by Streptomyces scabies. | Canadian journal of microbiology 20020401 |
| Herbicidal properties of the thaxtomin group of phytotoxins. | Journal of agricultural and food chemistry 20010501 |
| Production of thaxtomin a by two species of Streptomyces causing potato scab. | Acta microbiologica et immunologica Hungarica 20010101 |
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