NP-MRD: Showing NP-Card for (2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one (NP0192852)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 10:09:32 UTC

Updated at

2022-09-04 10:09:32 UTC

NP-MRD ID

NP0192852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one

Description

Tenuazonic acid, also known as tenuazonate, belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Tenuazonic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one is found in Alternaria alternata and Pyricularia grisea. (2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one was first documented in 2022 (PMID: 35922406). Based on a literature review a small amount of articles have been published on tenuazonic acid (PMID: 35989708) (PMID: 35946597) (PMID: 35893751) (PMID: 35878437).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.4610   -1.0047   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9831   -0.7219   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085    0.2807    0.7900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4511    1.5529    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589    0.5990    0.9478 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3217    1.1534   -0.2348 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844    0.5548   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227    0.9131   -1.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211   -0.5495    0.3000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0094   -0.3213    1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2388   -0.1612    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -0.2708    2.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853   -0.5663    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4671   -1.4203    2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799   -1.1522   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0839   -0.2090    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632   -1.9891    0.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -0.2903   -1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4496   -1.6633   -0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166   -0.1382    1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666    1.8205    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678    2.4110    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456    1.4723   -0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444    1.3324    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325    0.2319   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164   -1.5192   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3715   -1.0288   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    0.7487   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -0.0645    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  1  0
 13 14  2  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  1
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
  8 25  1  0
  9 26  1  6
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END


  Mrv1652309042212092D          

 14 14  0  0  1  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  9 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0192852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1N=C(O)C(C(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,7-8H,4H2,1-3H3,(H,11,14)/t5-,7?,8-/m0/s1

> <INCHI_KEY>
KLBSRSYHIIAQTG-PZICIZFRSA-N

> <FORMULA>
C10H15NO3

> <MOLECULAR_WEIGHT>
197.234

> <EXACT_MASS>
197.105193347

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.492673790924233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-acetyl-2-[(2S)-butan-2-yl]-5-hydroxy-3,4-dihydro-2H-pyrrol-3-one

> <JCHEM_LOGP>
1.901307384666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.84189783310418

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.742607924459978

> <JCHEM_PKA_STRONGEST_BASIC>
1.6071070898072626

> <JCHEM_POLAR_SURFACE_AREA>
66.73

> <JCHEM_REFRACTIVITY>
51.15370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
L-tenuazonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.306   1.175   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9    5   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
(5S,8S)-3-Acetyl-5-sec-butylpyrrolidine-2,4-dione	Kegg
Tenuazonate	Generator

Chemical Formula

C₁₀H₁₅NO₃

Average Mass

197.2340 Da

Monoisotopic Mass

197.10519 Da

IUPAC Name

(2S)-4-acetyl-2-[(2S)-butan-2-yl]-5-hydroxy-3,4-dihydro-2H-pyrrol-3-one

Traditional Name

L-tenuazonic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1N=C(O)C(C(C)=O)C1=O

InChI Identifier

InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,7-8H,4H2,1-3H3,(H,11,14)/t5-,7?,8-/m0/s1

InChI Key

KLBSRSYHIIAQTG-PZICIZFRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria alternata	LOTUS Database	35616633
Magnaporthe grisea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Beta-diketones

Alternative Parents

Substituents

1,3-diketone
Pyrrolidone
2-pyrrolidone
3-pyrrolidone
Pyrrolidine
Cyclic ketone
Secondary carboxylic acid amide
Carboxamide group
Lactam
Ketone
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organic amino compound (CHEBI:9440 )
ketone (CHEBI:9440 )
Mycotoxins (C08511 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.9	ChemAxon
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	1.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.73 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.15 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tenuazonic_acid

METLIN ID

Not Available

PubChem Compound

441580

PDB ID

Not Available

ChEBI ID

9440

Good Scents ID

Not Available

References

General References

Zhu HJ, Zhang B, Wei W, Liu SH, Xiang L, Zhu J, Jiao RH, Igarashi Y, Bashiri G, Liang Y, Tan RX, Ge HM: AvmM catalyses macrocyclization through dehydration/Michael-type addition in alchivemycin A biosynthesis. Nat Commun. 2022 Aug 3;13(1):4499. doi: 10.1038/s41467-022-32088-4. [PubMed:35922406 ]
Wang F, Yang YY, Wan DB, Li JD, Liang YF, Li ZF, Shen YD, Xu ZL, Yang JY, Wang H, Gettemans J, Hammock BD, Sun YM: Nanobodies for Accurate Recognition of Iso-tenuazonic Acid and Development of Sensitive Immunoassay for Contaminant Detection in Foods. Food Control. 2022 Jun;136:108835. doi: 10.1016/j.foodcont.2022.108835. Epub 2022 Jan 20. [PubMed:35989708 ]
de Oliveira RC, Mendonca CMN, Verissimo NV, de Almeida SRY, Correa B, Watanabe IS, de Azevedo POS, Oliveira RPS: Evaluating the potential of Pediococcus pentosaceus as a biocontrol agent against tenuazonic acid-producing Alternaria alternata on livestock feeds. J Appl Microbiol. 2022 Nov;133(5):3020-3029. doi: 10.1111/jam.15746. Epub 2022 Aug 10. [PubMed:35946597 ]
Ji X, Xiao Y, Lyu W, Li M, Wang W, Tang B, Wang X, Yang H: Probabilistic Risk Assessment of Combined Exposure to Deoxynivalenol and Emerging Alternaria Toxins in Cereal-Based Food Products for Infants and Young Children in China. Toxins (Basel). 2022 Jul 25;14(8):509. doi: 10.3390/toxins14080509. [PubMed:35893751 ]
Pavicich MA, Nielsen KF, Patriarca A: Morphological and chemical characterization of Alternaria populations from apple fruit. Int J Food Microbiol. 2022 Oct 16;379:109842. doi: 10.1016/j.ijfoodmicro.2022.109842. Epub 2022 Jul 20. [PubMed:35878437 ]
LOTUS database [Link]

Showing NP-Card for (2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one (NP0192852)

MOL for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

3D MOL for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

3D SDF for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

3D-SDF for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

PDB for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

3D PDB for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

SMILES for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

INCHI for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

Structure for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)

3D Structure for NP0192852 ((2s)-4-acetyl-2-[(2s)-butan-2-yl]-5-hydroxy-2,4-dihydropyrrol-3-one)