NP-MRD: Showing NP-Card for methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate (NP0205307)

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Record Information

Version

2.0

Created at

2022-09-05 01:11:18 UTC

Updated at

2022-09-05 01:11:18 UTC

NP-MRD ID

NP0205307

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate

Description

Methyl (Z)-5-(1-propynyl)-2-thienylacrylate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Methyl (Z)-5-(1-propynyl)-2-thienylacrylate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methyl (Z)-5-(1-propynyl)-2-thienylacrylate has been detected, but not quantified in, herbs and spices. This could make methyl (Z)-5-(1-propynyl)-2-thienylacrylate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308062D          

 14 14  0  0  0  0            999 V2000
   -1.2995   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8146   -1.4901    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  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
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  3  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205307

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C/C1=CC=C(S1)C#CC

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O2S/c1-3-4-9-5-6-10(14-9)7-8-11(12)13-2/h5-8H,1-2H3/b8-7-

> <INCHI_KEY>
XXSPOWNRZKCIRF-FPLPWBNLSA-N

> <FORMULA>
C11H10O2S

> <MOLECULAR_WEIGHT>
206.261

> <EXACT_MASS>
206.040150254

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.39856124175852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.547899826333333

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.797278192426722

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
55.1761

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.426  -4.028   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.275   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.521  -2.782   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.941   4.390   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0      -0.186   1.175   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2   13                                                            
CONECT    3    1    4                                                       
CONECT    4    3    9                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9    4    5   14                                                  
CONECT   10    6    7   14                                                  
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13    2   11                                                       
CONECT   14    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Methyl (Z)-5-(1-propynyl)-2-thienylacrylic acid	Generator
Methyl (2Z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoic acid	Generator

Chemical Formula

C₁₁H₁₀O₂S

Average Mass

206.2610 Da

Monoisotopic Mass

206.04015 Da

IUPAC Name

methyl (2Z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate

Traditional Name

methyl (2Z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C/C1=CC=C(S1)C#CC

InChI Identifier

InChI=1S/C11H10O2S/c1-3-4-9-5-6-10(14-9)7-8-11(12)13-2/h5-8H,1-2H3/b8-7-

InChI Key

XXSPOWNRZKCIRF-FPLPWBNLSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
2,5-disubstituted thiophene
Thiophene
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	3.41	ALOGPS
logP	3.55	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.18 m³·mol⁻¹	ChemAxon
Polarizability	22.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034858

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013428

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

131751629

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate (NP0205307)

MOL for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

3D MOL for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

3D SDF for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

3D-SDF for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

PDB for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

3D PDB for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

SMILES for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

INCHI for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

Structure for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)

3D Structure for NP0205307 (methyl (2z)-3-[5-(prop-1-yn-1-yl)thiophen-2-yl]prop-2-enoate)