NP-MRD: Showing NP-Card for 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene (NP0084678)

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Record Information

Version

2.0

Created at

2022-04-29 05:20:49 UTC

Updated at

2022-04-29 05:20:49 UTC

NP-MRD ID

NP0084678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene

Description

5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene, also known as triptolid or TPL, 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-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene is found in Tagetes erecta . 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    7.7795    0.3034   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3579    0.5153   -0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0555    1.2868   -1.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323   -0.1203    0.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0144    0.1350   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -0.6096    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -1.3319    1.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426   -0.5410    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4498   -0.4820    0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.3873    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023   -0.5804   -1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0466   -0.4389   -0.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.1149    0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9933    0.0911    0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0374   -0.0057   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2660    0.2213    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3642    0.5304    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7355    0.4926    2.0476 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2022   -0.0173    1.2635 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3894    1.1405   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8935    0.2117    0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0953   -0.6382   -0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    1.2224   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -0.1226   -1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.8456   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -0.5725   -1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8932   -0.2623   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2033    0.1737   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2868    0.7465    2.1060 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  2  0
  6  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 19  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 19 10  1  0
 18 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv0541 05061310282D          

 19 20  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
   -8.9595    2.4176    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
   -4.1849    1.9442    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
   -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
   -9.0458    3.2380    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
   -1.3271    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
   -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
   -3.4705    0.7067    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  4  3  0  0  0  0
  7  6  1  0  0  0  0
  8  2  2  0  0  0  0
 10  1  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  2  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  2  0  0  0  0
 17  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084678

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O3S2/c1-10(15)17-9-11(16)4-5-12-6-7-14(19-12)13-3-2-8-18-13/h2-3,6-8H,9H2,1H3

> <INCHI_KEY>
DTTMMEKKOHDZHY-UHFFFAOYSA-N

> <FORMULA>
C14H10O3S2

> <MOLECULAR_WEIGHT>
290.357

> <EXACT_MASS>
290.007135566

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.141713568595854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
3.439667547333333

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.0965473318785

> <JCHEM_PKA_STRONGEST_BASIC>
-6.947974802231669

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
71.55319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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     -16.724   4.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.218   4.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.812   3.629   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     -10.640   6.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.147   7.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.885   6.044   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      -2.477   3.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.478   2.859   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      -6.478   1.319   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.811   2.859   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0     -15.479   6.671   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0     -11.886   4.543   0.000  0.00  0.00           S+0
CONECT    1   10                                                            
CONECT    2    3    8                                                       
CONECT    3    2   13                                                       
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8    2   18                                                       
CONECT    9   11   17                                                       
CONECT   10    1   15   17                                                  
CONECT   11    4    9   16                                                  
CONECT   12    5    6   19                                                  
CONECT   13    3   14   18                                                  
CONECT   14    7   13   19                                                  
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17    9   10                                                       
CONECT   18    8   13                                                       
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
TPL	HMDB
Triptolid	HMDB
Triptolide	HMDB
Triptolide (9ci)	HMDB
Triptolide, tripterygium wilfordii	HMDB
4-{[2,2'-bithiophene]-5-yl}-2-oxobut-3-yn-1-yl acetic acid	Generator

Chemical Formula

C₁₄H₁₀O₃S₂

Average Mass

290.3570 Da

Monoisotopic Mass

290.00714 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H10O3S2/c1-10(15)17-9-11(16)4-5-12-6-7-14(19-12)13-3-2-8-18-13/h2-3,6-8H,9H2,1H3

InChI Key

DTTMMEKKOHDZHY-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
African marigold	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
Alpha-acyloxy ketone
Thiophene
Alpha,beta-unsaturated ketone
Heteroaromatic compound
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
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	3.35	ALOGPS
logP	3.44	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	17.1	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.55 m³·mol⁻¹	ChemAxon
Polarizability	30.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038459

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017818

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

131752377

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene (NP0084678)

MOL for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D MOL for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D SDF for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D-SDF for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

PDB for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D PDB for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

SMILES for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

INCHI for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

Structure for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D Structure for NP0084678 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)