NP-MRD: Showing NP-Card for {[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid (NP0299530)

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Record Information

Version

2.0

Created at

2022-09-10 11:24:10 UTC

Updated at

2022-09-10 11:24:10 UTC

NP-MRD ID

NP0299530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid

Description

Violaceimide C belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. {[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid is found in Aspergillus violaceus. Based on a literature review very few articles have been published on Violaceimide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    0.2438    3.3373    2.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3444    2.6993    1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.5712    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1705    1.1114    1.6986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658    0.9129   -0.5128 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1908    0.5322   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.6215    0.4744 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.9703    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3930    0.2346    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4847    0.9896   -0.8147 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563    0.5615    1.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351   -0.2148   -0.6357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655   -1.4173    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -1.5209    1.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759   -2.4553   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8463   -1.6602   -1.4726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1225   -1.5562   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -0.3355   -1.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    0.5194   -2.4569 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136    4.2351    2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021    3.6879    2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5673    2.6683    3.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115    1.6882   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2816    0.1029   -1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    1.4763   -0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.3095   -1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820   -1.7767    0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    0.2606    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -2.8225   -1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -3.2931   -0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -2.1144   -2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0157   -1.4773   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237   -2.4192    0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0209   -0.6239   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  6
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  6
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv1652309102213242D          

 19 19  0  0  1  0            999 V2000
    2.1285    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986   -0.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488   -0.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -1.5335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2889   -1.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290   -1.0657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -1.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9893   -0.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9091    0.1816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -2.1571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257   -2.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857   -3.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -3.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7957   -2.8467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9922   -3.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -2.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904   -1.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0299530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](CSCC(O)=O)N1C(=O)C[C@@H](C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO6S/c1-6-3-8(13)12(10(6)16)7(11(17)18-2)4-19-5-9(14)15/h6-7H,3-5H2,1-2H3,(H,14,15)/t6-,7-/m1/s1

> <INCHI_KEY>
XGOZKMUGJUCPHS-RNFRBKRXSA-N

> <FORMULA>
C11H15NO6S

> <MOLECULAR_WEIGHT>
289.3

> <EXACT_MASS>
289.062008381

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.423527148314896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2S)-3-methoxy-2-[(3R)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid

> <JCHEM_LOGP>
-0.43195701566666644

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8492232216230207

> <JCHEM_PKA_STRONGEST_BASIC>
-6.784081077441835

> <JCHEM_POLAR_SURFACE_AREA>
100.98

> <JCHEM_REFRACTIVITY>
65.70970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{[(2S)-3-methoxy-2-[(3R)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.973   0.339   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.477  -1.116   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.990  -1.407   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.998  -0.243   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.494  -2.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.006  -3.153   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       9.014  -1.989   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      10.526  -2.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.534  -1.116   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.047  -1.407   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      11.030   0.339   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.485  -4.027   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.835  -5.526   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.253  -6.126   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.516  -6.322   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.352  -5.314   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.852  -5.663   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.951  -3.895   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.155  -2.577   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₅NO₆S

Average Mass

289.3000 Da

Monoisotopic Mass

289.06201 Da

IUPAC Name

2-{[(2S)-3-methoxy-2-[(3R)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid

Traditional Name

{[(2S)-3-methoxy-2-[(3R)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](CSCC(O)=O)N1C(=O)C[C@@H](C)C1=O

InChI Identifier

InChI=1S/C11H15NO6S/c1-6-3-8(13)12(10(6)16)7(11(17)18-2)4-19-5-9(14)15/h6-7H,3-5H2,1-2H3,(H,14,15)/t6-,7-/m1/s1

InChI Key

XGOZKMUGJUCPHS-RNFRBKRXSA-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
Aspergillus violaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Cysteine or derivatives
Heterocyclic fatty acid
Fatty acyl
Fatty acid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Carboxylic acid imide, n-substituted
Dicarboxylic acid or derivatives
Methyl ester
Pyrrolidine
Dicarboximide
Carboxylic acid imide
Lactam
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-0.43	ChemAxon
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	65.71 m³·mol⁻¹	ChemAxon
Polarizability	27.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

71048474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid (NP0299530)

MOL for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

3D MOL for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

3D SDF for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

3D-SDF for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

PDB for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

3D PDB for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

SMILES for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

INCHI for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

Structure for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)

3D Structure for NP0299530 ({[(2s)-3-methoxy-2-[(3r)-3-methyl-2,5-dioxopyrrolidin-1-yl]-3-oxopropyl]sulfanyl}acetic acid)