NP-MRD: Showing NP-Card for 3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid (NP0221995)

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Record Information

Version

2.0

Created at

2022-09-05 23:42:56 UTC

Updated at

2022-09-05 23:42:56 UTC

NP-MRD ID

NP0221995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid

Description

3-(Methylsulfanyl)-N-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid belongs to the class of organic compounds known as vinylogous thioesters. These are organic compounds containing a thioester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. 3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid is found in Aglaia tenuicaulis. 3-(Methylsulfanyl)-N-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171500462D          

 18 17  0  0  0  0            999 V2000
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC=CC(=O)NCCCCOC(=O)C=CSC

> <INCHI_IDENTIFIER>
InChI=1S/C12H19NO3S2/c1-17-9-5-11(14)13-7-3-4-8-16-12(15)6-10-18-2/h5-6,9-10H,3-4,7-8H2,1-2H3,(H,13,14)

> <INCHI_KEY>
GVFWUEUUBBYYPB-UHFFFAOYSA-N

> <FORMULA>
C12H19NO3S2

> <MOLECULAR_WEIGHT>
289.41

> <EXACT_MASS>
289.080635824

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.404855970284903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[3-(methylsulfanyl)prop-2-enamido]butyl 3-(methylsulfanyl)prop-2-enoate

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.7344651513333345

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.5687096967056

> <JCHEM_PKA_STRONGEST_BASIC>
-0.35332944682566036

> <JCHEM_POLAR_SURFACE_AREA>
55.4

> <JCHEM_REFRACTIVITY>
79.31

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[3-(methylsulfanyl)prop-2-enamido]butyl 3-(methylsulfanyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       1.595   4.001   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       6.930   4.001   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.598   4.771   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0      18.933   4.771   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0      18.933   6.311   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-(Methylsulfanyl)-N-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidate	Generator
3-(Methylsulphanyl)-N-(4-{[3-(methylsulphanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidate	Generator
3-(Methylsulphanyl)-N-(4-{[3-(methylsulphanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid	Generator

Chemical Formula

C₁₂H₁₉NO₃S₂

Average Mass

289.4100 Da

Monoisotopic Mass

289.08064 Da

IUPAC Name

4-[3-(methylsulfanyl)prop-2-enamido]butyl 3-(methylsulfanyl)prop-2-enoate

Traditional Name

4-[3-(methylsulfanyl)prop-2-enamido]butyl 3-(methylsulfanyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CSC=CC(=O)NCCCCOC(=O)C=CSC

InChI Identifier

InChI=1S/C12H19NO3S2/c1-17-9-5-11(14)13-7-3-4-8-16-12(15)6-10-18-2/h5-6,9-10H,3-4,7-8H2,1-2H3,(H,13,14)

InChI Key

GVFWUEUUBBYYPB-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
Aglaia tenuicaulis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous thioesters. These are organic compounds containing a thioester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous thioesters

Sub Class

Not Available

Direct Parent

Vinylogous thioesters

Alternative Parents

Substituents

Vinylogous thioester
Acrylic acid or derivatives
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Thioenolether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Sulfenyl compound
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.84	ALOGPS
logP	1.73	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.57	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	79.31 m³·mol⁻¹	ChemAxon
Polarizability	31.4 Å³	ChemAxon
Number of Rings	0	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid (NP0221995)

MOL for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

3D MOL for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

3D SDF for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

3D-SDF for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

PDB for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

3D PDB for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

SMILES for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

INCHI for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

Structure for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)

3D Structure for NP0221995 (3-(methylsulfanyl)-n-(4-{[3-(methylsulfanyl)prop-2-enoyl]oxy}butyl)prop-2-enimidic acid)