NP-MRD: Showing NP-Card for 1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol (NP0084677)

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Record Information

Version

2.0

Created at

2022-04-29 05:20:47 UTC

Updated at

2022-04-29 05:20:47 UTC

NP-MRD ID

NP0084677

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol

Description

5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene, also known as 1-chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol, 8CI, 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. 5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene has been detected, but not quantified in, herbs and spices. 1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol is found in Pterocaulon virgatum and Tagetes minuta . This could make 5-(4-chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307012D          

 16 17  0  0  0  0            999 V2000
    3.2088   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787    4.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938    3.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289    2.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4841    5.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6636    5.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9690    5.7924    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3280    5.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638    2.4242    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  3  0  0  0  0
  6  5  1  0  0  0  0
  7  1  2  0  0  0  0
  9  3  1  0  0  0  0
  9  8  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  2  2  0  0  0  0
 12  6  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CCl)C#CC1=CC=C(S1)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C12H9ClOS2/c13-8-9(14)3-4-10-5-6-12(16-10)11-2-1-7-15-11/h1-2,5-7,9,14H,8H2

> <INCHI_KEY>
GFYWABYZRGXGNU-UHFFFAOYSA-N

> <FORMULA>
C12H9ClOS2

> <MOLECULAR_WEIGHT>
268.782

> <EXACT_MASS>
267.978333997

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.945405059042315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.82

> <JCHEM_LOGP>
3.7379578186666667

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.546966278723328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8717569496864153

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.2194

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

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

> <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       5.990  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.466   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.800   8.482   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.895   7.236   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.450   5.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.974   4.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.450  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.237   9.566   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.705   9.727   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.990   5.990   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.220   2.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.220   3.620   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      11.142  10.812   0.000  0.00  0.00          Cl+0
HETATM   14  O   UNK     0       8.079  11.134   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       3.974   1.175   0.000  0.00  0.00           S+0
HETATM   16  S   UNK     0       6.466   4.525   0.000  0.00  0.00           S+0
CONECT    1    2    7                                                       
CONECT    2    1   11                                                       
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7    1   15                                                       
CONECT    8    9   13                                                       
CONECT    9    3    8   14                                                  
CONECT   10    4    5   16                                                  
CONECT   11    2   12   15                                                  
CONECT   12    6   11   16                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    7   11                                                       
CONECT   16   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol, 8ci	HMDB

Chemical Formula

C₁₂H₉ClOS₂

Average Mass

268.7820 Da

Monoisotopic Mass

267.97833 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC(CCl)C#CC1=CC=C(S1)C1=CC=CS1

InChI Identifier

InChI=1S/C12H9ClOS2/c13-8-9(14)3-4-10-5-6-12(16-10)11-2-1-7-15-11/h1-2,5-7,9,14H,8H2

InChI Key

GFYWABYZRGXGNU-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pterocaulon virgatum	LOTUS Database	35616633
Tagetes minuta	Plant	KNApSAcK

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
Secondary alcohol
Halohydrin
Chlorohydrin
Alcohol
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Alkyl halide
Alkyl chloride
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	3.82	ALOGPS
logP	3.74	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.22 m³·mol⁻¹	ChemAxon
Polarizability	27.95 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

HMDB0033269

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011292

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

85528914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol (NP0084677)

MOL for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

3D MOL for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

3D SDF for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

3D-SDF for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

PDB for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

3D PDB for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

SMILES for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

INCHI for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

Structure for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)

3D Structure for NP0084677 (1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol)