NP-MRD: Showing NP-Card for 4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate (NP0195744)

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Record Information

Version

2.0

Created at

2022-09-04 13:39:54 UTC

Updated at

2022-09-04 13:39:54 UTC

NP-MRD ID

NP0195744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate

Description

5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene, also known as 4-(2,2'-bithien-5-yl)but-3-yn-1-yl acetate, belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms. Thus, 5-(4-acetoxy-1-butynyl)-2,2'-bithiophene is considered to be an oxygenated hydrocarbon lipid molecule. 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene has been detected, but not quantified in, herbs and spices. 4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate is found in Tagetes erecta. This could make 5-(4-acetoxy-1-butynyl)-2,2'-bithiophene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -7.3679    0.4245   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8768    0.4169   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2433    1.4570    0.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1893   -0.7130   -0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7874   -0.7614   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601   -0.4712    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -0.5332    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133   -0.5830    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329   -0.6226    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -1.4900   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892   -1.3303   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144   -0.3370   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0337    0.0339    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5804    1.0226    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9140    1.1618    0.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6180    0.2848    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3868   -0.6945   -0.5858 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426    0.3741    0.7147 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6002    0.5424    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7959   -0.5140   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7226    1.2913   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4952   -1.7848   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -0.0446   -1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3176    0.5255    0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051   -1.2109    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2174   -2.2720   -1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7564   -1.9852   -1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423    1.6989    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813    1.9354    1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7116    0.2404   -0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 18  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 18  9  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv0541 05061307492D          

 18 19  0  0  0  0            999 V2000
   -0.6126    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9595    2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8994    2.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1526    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    3.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5071    3.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7560    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0458    3.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6139    2.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7401    2.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9196    3.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271    2.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415    1.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2921    3.5736    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676    2.4337    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  2  3  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  1  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  6  2  0  0  0  0
 14  8  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O2S2/c1-11(15)16-9-3-2-5-12-7-8-14(18-12)13-6-4-10-17-13/h4,6-8,10H,3,9H2,1H3

> <INCHI_KEY>
KHPAKGUGOFYJNA-UHFFFAOYSA-N

> <FORMULA>
C14H12O2S2

> <MOLECULAR_WEIGHT>
276.374

> <EXACT_MASS>
276.027871008

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.132654216023088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

> <ALOGPS_LOGP>
4.61

> <JCHEM_LOGP>
3.7434875199999995

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.976341584319819

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
71.1124

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

> <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      -1.144   2.859   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.812   3.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.478   2.859   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.724   4.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.146   4.399   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -15.218   4.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.640   6.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.147   7.021   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.145   3.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -16.885   6.044   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.477   3.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.479   5.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.448   5.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.917   5.687   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.477   5.169   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.811   2.859   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0     -15.479   6.671   0.000  0.00  0.00           S+0
HETATM   18  S   UNK     0     -11.886   4.543   0.000  0.00  0.00           S+0
CONECT    1   11                                                            
CONECT    2    3    5                                                       
CONECT    3    2    9                                                       
CONECT    4    6   10                                                       
CONECT    5    2   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9    3   16                                                       
CONECT   10    4   17                                                       
CONECT   11    1   15   16                                                  
CONECT   12    5    7   18                                                  
CONECT   13    6   14   17                                                  
CONECT   14    8   13   18                                                  
CONECT   15   11                                                            
CONECT   16    9   11                                                       
CONECT   17   10   13                                                       
CONECT   18   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
4-(5-(2-Thienyl)-2-thienyl)-3-butyn-1-ol acetate	ChEBI
4-(5-(2-Thienyl)-2-thienyl)-3-butyn-1-ol acetic acid	Generator
3-Butyn-1-ol, 4-(5-(2-thienyl)-2-thienyl)-, acetate	HMDB
4-(2,2'-Bithien-5-yl)but-3-yn-1-yl acetate	HMDB
5-(4-Acetoxybut-1-ynyl)-2,2'-bithiophene	HMDB
5-(4-Acetoxybut-1-ynyl)-2-2'-bithiophene	HMDB
5-4-ACETOXYBUT-1-ynyl-2-2-bithiophene	HMDB
4-([2,2'-Bithiophen]-5-yl)but-3-yn-1-yl acetic acid	Generator

Chemical Formula

C₁₄H₁₂O₂S₂

Average Mass

276.3740 Da

Monoisotopic Mass

276.02787 Da

IUPAC Name

4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

Traditional Name

4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS1

InChI Identifier

InChI=1S/C14H12O2S2/c1-11(15)16-9-3-2-5-12-7-8-14(18-12)13-6-4-10-17-13/h4,6-8,10H,3,9H2,1H3

InChI Key

KHPAKGUGOFYJNA-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
African marigold	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Bi- and oligothiophenes

Sub Class

Not Available

Direct Parent

Bi- and oligothiophenes

Alternative Parents

Substituents

Bithiophene
2,5-disubstituted thiophene
Heteroaromatic compound
Thiophene
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

2,2'-bithiophenes (CHEBI:17181 )
a small molecule (5-4-ACETOXYBUT-1-YNYL-2-2-BITHIOPHENE )

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	4.61	ALOGPS
logP	3.74	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-7	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	6	ChemAxon
Refractivity	71.11 m³·mol⁻¹	ChemAxon
Polarizability	30.13 Å³	ChemAxon
Number of Rings	2	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

HMDB0034454

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012863

KNApSAcK ID

Not Available

Chemspider ID

389319

KEGG Compound ID

C04485

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440356

PDB ID

Not Available

ChEBI ID

17181

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate (NP0195744)

MOL for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

3D MOL for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

3D SDF for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

3D-SDF for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

PDB for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

3D PDB for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

SMILES for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

INCHI for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

Structure for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)

3D Structure for NP0195744 (4-{[2,2'-bithiophen]-5-yl}but-3-yn-1-yl acetate)