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3-[(4-Hydroxyphenyl)Methyl]-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

Basic information

CPKB ID CP00276
IUPAC Name
3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms
3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
3-(4-Hydroxybenzyl)Octahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
3-[(4-Hydroxyphenyl)Methyl]-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
5654-84-2
Akos015954954
Chebi:176817
Chembl1980823
Cyclo(-Pro-Tyr)
Cyclo(Tyr-Pro)
Dtxsid601157236
Hexahydro-3-[(4-Hydroxyphenyl)Methyl]Pyrrolo[1,2-A]Pyrazine-1,4-Dione
Megxm0_000419
Ncgc00384639-01
Nci60_015871
Nsc646120
Nsc-646120
Schembl4320879
Sr-01000089494
Sr-01000089494-1
Source

Microdochium nivale [Division : Plants and Fungi]

Taxonomy :5520 (Fungi-Ascomycota-Xylariales-Sordariomycetes-Microdochiaceae Microdochium)  

Wikipedia: Microdochium nivale

Alternaria alternata [Division : Plants and Fungi]

Taxonomy :5599 (Fungi-Ascomycota-Pleosporales-Dothideomycetes-Pleosporaceae Alternaria)  

Wikipedia: Alternaria alternata

PubChem  

Information

3-[(4-Hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is a natural product found in Microdochium nivale and Alternaria alternata with data available. 7-aminoactinomycin D is a chromopeptide. It has a role as a fluorochrome.

PubChem|371682  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C14H16N2O3
Molecular Weight 260.1160924 g/mol
SMILES

RUN SEA Predictions

 O=C1N[C@H](Cc2ccc(O)cc2)C(=O)N2CCC[C@@H]12  

PubChem|371682
InChI
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)  
InChIKey
LSGOTAXPWMCUCK-USGQBGAGNA-N
2D Structure
PubChem|371682
3D Structure
PubChem|371682

Sequence

Graph alignment
Local alignment
One letter code from Structure
YP  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Tyr--Pro  

CyclicPepedia|Struct2seq
Description of the conversion sequence The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 260.1160924
Number of Rings 3.0
Complexity 1.263157895
XlogP3 AA 0.4241
Heavy Atom Count 19.0
Hydrogen Bond Donor Count 2.0
Hydrogen Bond Acceptor Count 3.0
Rotatable Bond Count 2.0
Property Name Property Value
Formal Charge 0.0
Refractivity 68.4765
Rule_of_Five 1.0
Number of Atoms 19.0
Topological Polar Surface Area 69.64
Refractivity 68.4765
Veber Rule 1.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000010100000100100100011011000010000100111010000101010000000000010101111101000100110000010110010000101000001001010001000110010000001001000111000001111000100100100001010100010100110011111100100100100101001001000000000000000010100000101001110001100011100101111000110001000000010001001100000000010011010010000001001000001010100000010111011010110101000000010011000000001000010000000000000000010010100000100000100001100000010000000101000110011110011100000000100010110111000010000000000000010001010010100100000101100110000000100100110010101100110000100100010010110001000000100010010000000000000011000101000110001100010011000100000001001100000110110000010100110000001000110001010000000000100011100011100010000100101000000000100100011001001011000100010000010001110101010001110010010000001100001001010001000001000001000100000001001111010110000010011101001010000110010011101000001010100000100111000000011001101000010111000010100011100011010000000011110001000001010010101010000011000010100001000000001010100000000000000101101001101110011110110001010100000001010000000001010101001100001000001001001110110000001001101010010000000101000000110001001010010000000101000001000100110100110100111001000010010001110000001000000000001011101010010100000011100110111000010010000100101000010001000100000000000110000110001001001011010100001000001100010100001000011101110000001010110110001010000010000000101001000001000000101100000001100000001000101100010001000000011111110001101001011000100000110010000100001010000111011011001000000100100100111000000100000000000010000010010100100000010100000000110100110001001010101100010010001000010000001000000100010110000000100000000100010010000000001000011000100101010000101000010000001011110000100100101000001010110001000100000100011011001010100000010010110100000000000100001010010000000000011111001101100000010110000011110100111110011000000100000000000100011100000010000001101101100000100101101000001010000010001010010000111110110000001011001011001001000000011001001100110000001000000100010010000000001101110000100000000101000000011
Morgan Fingerprint
0000110000100000000100000000100000000000000000000000000000000000000000000000000010000000001000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000001100000000000100000000100010000000000000000000000000100000000000000010000000000000000000000000000000000000000000000000000000000000000000000000001000000000000010000000001010000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000000000000000000000000000000000001000100000000000000100000000100000000000000000000000000000000000000000000000000001000100000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000010000000010000000000000000000001000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000000000000000000000000000001000101000011100110101100110000110100011011100001110100001101001101111011111111110111110

Sequence Properties

Property Name Property Value
Boman Index 0.07
Charge -0.00286611482556564

Manufacturers

Forecasting tools

Forecasting tools Value
Structure to Sequence
Structure Properties
Sequence to Structure
YP
Sequence Properties
YP
Expasy ProtParam Tool YP
SEA RUN SEA Predictions

Information Source

Reference

Pubmed_ID Title DOI Journal

14695551

 Highly efficient biomimetic total synthesis and structural verification of bistratamides E and J from Lissoclinum bistratum 10.1002/chem.200305504.

Chemistry

Highly efficient biomimetic total synthesis and structural verification of bistratamides E and J from Lissoclinum bistratum

Abstract

  • The interesting biological activities of heterocycle-containing cyclic peptide-derived natural products, isolated from marine organisms over the past twenty years, have attracted the interest of many synthetic and natural products chemists. Bistratamides E-J, members of this class of natural products that were isolated very recently from Lissoclinum bistratum, exhibited cytotoxic activity against a human colon tumor (HCT-116) cell line. Here we report the first total syntheses of bistratamides E (1) and J (2) in overall yields of 19 and 34 %, respectively. The thiazole substructures have been synthesized by oxidation of their corresponding thiazoline substructures, which were obtained from cysteine containing peptides using a novel biomimetic approach wherein Val-Cys dipeptide units were converted to thiazolines by a bisphosphonium salt. The final macrocyclization was promoted efficiently using the combination of PyBOP and DMAP. This approach allows the use of readily available Fmoc-protected amino acids to make complex thiazole and oxazoline-containing natural products.