NP-MRD: Showing NP-Card for 3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate (NP0321430)

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Record Information

Version

2.0

Created at

2022-09-11 23:38:01 UTC

Updated at

2022-09-11 23:38:01 UTC

NP-MRD ID

NP0321430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate

Description

3-(Hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1λ⁴,2-dithiin-1-one belongs to the class of organic compounds known as dithiins. Dithiins are compounds comprising a dithiin ring, which is an unsaturated six-member heterocycle containing four carbon atoms, two sulfur atoms and two double bonds. 3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate is found in Ambrosia chamissonis. 3-(Hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1λ⁴,2-dithiin-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251513422D          

 16 16  0  0  0  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  3  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  3  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC#CC1=CC=C(SS1=O)C#CC#CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C13H8OS2/c1-3-5-6-7-9-12-10-11-13(8-4-2)16(14)15-12/h3,10-11H,1H2,2H3

> <INCHI_KEY>
BSMKHCHYHFVZRI-UHFFFAOYSA-N

> <FORMULA>
C13H8OS2

> <MOLECULAR_WEIGHT>
244.33

> <EXACT_MASS>
244.001657226

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
26.899884861522537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1λ⁴,2-dithiin-1-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.5890000000000004

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.016206509985177

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
75.6243

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1λ⁴,2-dithiin-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0       0.000   1.540   0.000  0.00  0.00           S+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₈OS₂

Average Mass

244.3300 Da

Monoisotopic Mass

244.00166 Da

IUPAC Name

3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1λ⁴,2-dithiin-1-one

Traditional Name

3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1λ⁴,2-dithiin-1-one

CAS Registry Number

Not Available

SMILES

CC#CC1=CC=C(SS1=O)C#CC#CC=C

InChI Identifier

InChI=1S/C13H8OS2/c1-3-5-6-7-9-12-10-11-13(8-4-2)16(14)15-12/h3,10-11H,1H2,2H3

InChI Key

BSMKHCHYHFVZRI-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
Ambrosia chamissonis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithiins. Dithiins are compounds comprising a dithiin ring, which is an unsaturated six-member heterocycle containing four carbon atoms, two sulfur atoms and two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiins

Sub Class

Not Available

Direct Parent

Dithiins

Alternative Parents

Substituents

1,2-dithiin
Thiosulfinic acid ester
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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
logP	3.55	ALOGPS
logP	3.59	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.62 m³·mol⁻¹	ChemAxon
Polarizability	26.9 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

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

14777884

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate (NP0321430)

MOL for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

3D MOL for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

3D SDF for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

3D-SDF for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

PDB for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

3D PDB for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

SMILES for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

INCHI for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

Structure for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)

3D Structure for NP0321430 (3-(hex-5-en-1,3-diyn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiin-1-ium-1-olate)