NP-MRD: Showing NP-Card for 1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone (NP0156750)

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Record Information

Version

2.0

Created at

2022-09-02 14:00:11 UTC

Updated at

2022-09-02 14:00:11 UTC

NP-MRD ID

NP0156750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone

Description

Tenuazonic acid, also known as tenuazonate or vivotoxin, belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. Tenuazonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Tenuazonic acid is a potentially toxic compound. It inhibits the protein synthesis machinery. Tenuazonic acid is produced by Aspergillus species Causes rice leaf rot Tenuazonic acid is a mycotoxin. 1-[2,4-dihydroxy-5-(sec-butyl)-5h-pyrrol-3-yl]ethanone is found in Alternaria alternata and Pyricularia grisea. Tenuazonic acid is a mycotoxin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.9567    1.2371   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -0.2017   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5191   -0.7758   -0.1657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4374   -0.6794    1.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -0.3627   -0.8901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0108    1.0168   -0.9490 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3075    1.2120   -0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    2.3044   -0.3010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8389   -0.0755   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1407   -0.3799    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0647    0.7487    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5133   -1.5304    0.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379   -0.9988   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807   -2.3548   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.8807   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749    1.3406    0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    1.6207    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6637   -0.8288   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116   -0.3248   -1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -1.9029   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8640    0.2057    1.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0215   -1.6063    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578   -0.5624    1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519   -0.8446   -1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    1.7821   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0252    0.4084    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2646    1.2792   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5940    1.4534    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7276   -3.0611   -0.6762 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  2  0
 13 14  1  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  6
  6 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
M  END


  Mrv0541 02241215302D          

 14 14  0  0  0  0            999 V2000
    1.9804   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -1.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475   -0.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    0.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1546   -1.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775   -0.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775    0.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    1.0311    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
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0156750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1NC(=O)C(C(C)=O)=C1O

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

> <INCHI_KEY>
CEIZFXOZIQNICU-UHFFFAOYSA-N

> <FORMULA>
C10H15NO3

> <MOLECULAR_WEIGHT>
197.231

> <EXACT_MASS>
197.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.60632372310234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
0.5687822743333341

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.049430920367062

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8067589277166642

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5461083056826469

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
52.73030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-acetyl-4-hydroxy-5-(sec-butyl)-1,5-dihydropyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.697  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.926   0.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.697   1.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.926   3.003   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.923  -2.541   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.462  -1.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.386   0.231   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.462   1.463   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -2.155  -3.003   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.310  -1.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.697  -0.846   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.078  -0.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.078   1.001   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.310   1.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7   12                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7   13                                                       
CONECT    9   10                                                            
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12    6   10   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Tenuazonate	Generator
3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one, 9ci	HMDB
3-Acetyl-5-sec-butyl-4-hydroxy-L-3-pyrrolin-2-one	HMDB
3-Acetyl-5-sec-butyl-pyrrole-2,4-diol	HMDB
3-Acetyl-5-sec-butyltetramic acid	HMDB
L-Tenuazonic acid	HMDB
Vivotoxin	HMDB
Acid, tenuazonic	HMDB
Tenuazonic acid	MeSH

Chemical Formula

C₁₀H₁₅NO₃

Average Mass

197.2310 Da

Monoisotopic Mass

197.10519 Da

IUPAC Name

3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

3-acetyl-4-hydroxy-5-(sec-butyl)-1,5-dihydropyrrol-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)C1NC(=O)C(C(C)=O)=C1O

InChI Identifier

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

InChI Key

CEIZFXOZIQNICU-UHFFFAOYSA-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 pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
Vinylogous acid
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Enol
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.17	ALOGPS
logP	0.57	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.73 m³·mol⁻¹	ChemAxon
Polarizability	20.61 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