NP-MRD: Showing NP-Card for 2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid (NP0258988)

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Record Information

Version

2.0

Created at

2022-09-08 00:42:10 UTC

Updated at

2022-09-08 00:42:11 UTC

NP-MRD ID

NP0258988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid

Description

2-[(2S)-4-ethyl-3-hydroxy-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-5-oxo-2,5-dihydrothiophen-2-yl]ethanimidic acid belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. 2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid is found in Streptomyces olivaceus. Based on a literature review very few articles have been published on 2-[(2S)-4-ethyl-3-hydroxy-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-5-oxo-2,5-dihydrothiophen-2-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.7894    3.3512    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6906    2.5673    0.6645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    2.7005   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260    4.0042   -0.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    1.6183   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667    0.2477   -0.9169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6814    0.1735   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678   -0.8287    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.9638    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221   -0.8188    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -1.7517    0.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -0.9129   -2.2151 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380   -1.0420   -1.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9131   -1.4008   -2.1480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757   -0.6573   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8238   -0.9914    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018   -0.3083    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -0.0264    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3600    0.3916    1.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    4.7870   -0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217    1.8129   -2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424    1.6600   -1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690    0.9884   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231   -1.9208    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1066   -2.8783    0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182   -2.2279   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2793    0.0576   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4369   -1.6658    1.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867   -2.6289    1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135   -2.0787    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -0.7212    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8874    0.6478   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6427   -0.9403   -0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7670   -0.1063    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1052    0.8622    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 18  2  0
 18 19  1  0
 18  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  6 12  1  0
 12 13  1  0
 13 14  2  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 13 15  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 16 30  1  0
 16 31  1  0
 19 35  1  0
  5 21  1  0
  5 22  1  0
  4 20  1  0
  2  1  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END


  Mrv1652309082202422D          

 18 18  0  0  1  0            999 V2000
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    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
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2707    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2814    3.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0776    2.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 S   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
   -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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C(O)[C@@](CC(O)=N)(SC1=O)\C=C(/C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C13H17NO3S/c1-4-8(3)6-13(7-10(14)15)11(16)9(5-2)12(17)18-13/h4,6,16H,1,5,7H2,2-3H3,(H2,14,15)/b8-6+/t13-/m1/s1

> <INCHI_KEY>
GNZUNOUXZMJOPW-STMXVASLSA-N

> <FORMULA>
C13H17NO3S

> <MOLECULAR_WEIGHT>
267.34

> <EXACT_MASS>
267.092914585

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.280093889982645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S)-4-ethyl-3-hydroxy-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-5-oxo-2,5-dihydrothiophen-2-yl]ethanimidic acid

> <JCHEM_LOGP>
-0.2829435187182357

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.4504644633954635

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.6840761027597528

> <JCHEM_PKA_STRONGEST_BASIC>
13.140596375032429

> <JCHEM_POLAR_SURFACE_AREA>
81.38

> <JCHEM_REFRACTIVITY>
85.407

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S)-4-ethyl-3-hydroxy-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.151   5.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.627   4.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.597   2.904   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.073   1.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.505   4.689   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.525   5.834   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.012   5.009   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       2.306   1.175   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   18  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                                                       
CONECT    6    5    7   11   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    6   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-[(2S)-4-Ethyl-3-hydroxy-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-5-oxo-2,5-dihydrothiophen-2-yl]ethanimidate	Generator

Chemical Formula

C₁₃H₁₇NO₃S

Average Mass

267.3400 Da

Monoisotopic Mass

267.09291 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC1=C(O)[C@@](CC(O)=N)(SC1=O)\C=C(/C)C=C

InChI Identifier

InChI=1S/C13H17NO3S/c1-4-8(3)6-13(7-10(14)15)11(16)9(5-2)12(17)18-13/h4,6,16H,1,5,7H2,2-3H3,(H2,14,15)/b8-6+/t13-/m1/s1

InChI Key

GNZUNOUXZMJOPW-STMXVASLSA-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
Streptomyces olivaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Fatty amide
Fatty acyl
2,5-dihydrothiophene
Vinylogous acid
Carbothioic s-lactone
Carboxamide group
Primary carboxylic acid amide
Thiocarboxylic acid ester
Carboxylic acid derivative
Enol
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163084632

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid (NP0258988)

MOL for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

3D MOL for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

3D SDF for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

3D-SDF for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

PDB for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

3D PDB for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

SMILES for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

INCHI for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

Structure for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)

3D Structure for NP0258988 (2-[(2s)-4-ethyl-3-hydroxy-2-[(1e)-2-methylbuta-1,3-dien-1-yl]-5-oxothiophen-2-yl]ethanimidic acid)