NP-MRD: Showing NP-Card for (3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione (NP0219362)

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Record Information

Version

2.0

Created at

2022-09-05 20:19:40 UTC

Updated at

2022-09-05 20:19:40 UTC

NP-MRD ID

NP0219362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione

Description

(3S)-1,4-Dimethyl-3alpha,6alpha-bis(methylthio)-3-[4-(prenyloxy)benzyl]piperazine-2,5-dione belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione is found in Penicillium solitum. Based on a literature review very few articles have been published on (3S)-1,4-Dimethyl-3alpha,6alpha-bis(methylthio)-3-[4-(prenyloxy)benzyl]piperazine-2,5-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222192D          

 27 28  0  0  1  0            999 V2000
    2.4256   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -4.0752    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -3.2502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9966   -2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -3.2502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -2.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -1.6002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1808   -0.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630   -0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9327    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2148    1.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    2.1327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219    2.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    3.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    3.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0613    3.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560    4.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754   -0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.9683    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -2.8377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -3.2502    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
  8 22  1  1  0  0  0
 22 23  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv1652309052222192D          

 27 28  0  0  1  0            999 V2000
    2.4256   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -4.0752    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -3.2502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9966   -2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -3.2502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -2.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -1.6002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1808   -0.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630   -0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9327    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2148    1.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    2.1327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219    2.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    3.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    3.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0613    3.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560    4.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754   -0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.9683    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -2.8377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -3.2502    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
  8 22  1  1  0  0  0
 22 23  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS[C@@H]1N(C)C(=O)[C@](CC2=CC=C(OCC=C(C)C)C=C2)(SC)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N2O3S2/c1-14(2)11-12-25-16-9-7-15(8-10-16)13-20(27-6)19(24)21(3)18(26-5)17(23)22(20)4/h7-11,18H,12-13H2,1-6H3/t18-,20-/m0/s1

> <INCHI_KEY>
XBKBUMFBHNQOLC-ICSRJNTNSA-N

> <FORMULA>
C20H28N2O3S2

> <MOLECULAR_WEIGHT>
408.58

> <EXACT_MASS>
408.154135118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.62835309641173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione

> <JCHEM_LOGP>
3.972160463666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.036165170310955

> <JCHEM_PKA_STRONGEST_BASIC>
-4.856840211257786

> <JCHEM_POLAR_SURFACE_AREA>
49.85

> <JCHEM_REFRACTIVITY>
114.5019

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.528  -8.377   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       3.194  -7.607   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       3.194  -6.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.860  -5.297   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.527  -6.067   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       1.860  -3.757   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.527  -2.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.194  -2.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.204  -1.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.731  -0.360   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.741   0.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.268   2.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.784   2.534   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.311   3.981   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.828   4.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.354   5.696   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.364   6.875   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.848   6.608   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.891   8.322   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.774   1.354   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.247  -0.093   0.000  0.00  0.00           C+0
HETATM   22  S   UNK     0       4.184  -1.807   0.000  0.00  0.00           S+0
HETATM   23  C   UNK     0       5.701  -2.075   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.528  -3.757   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.861  -2.987   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       4.528  -5.297   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       5.861  -6.067   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   22   24                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13   21                                                       
CONECT   21   20   10                                                       
CONECT   22    8   23                                                       
CONECT   23   22                                                            
CONECT   24    8   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    3   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
(3S)-1,4-Dimethyl-3a,6a-bis(methylthio)-3-[4-(prenyloxy)benzyl]piperazine-2,5-dione	Generator
(3S)-1,4-Dimethyl-3α,6α-bis(methylthio)-3-[4-(prenyloxy)benzyl]piperazine-2,5-dione	Generator

Chemical Formula

C₂₀H₂₈N₂O₃S₂

Average Mass

408.5800 Da

Monoisotopic Mass

408.15414 Da

IUPAC Name

(3S,6S)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione

Traditional Name

(3S,6S)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

CS[C@@H]1N(C)C(=O)[C@](CC2=CC=C(OCC=C(C)C)C=C2)(SC)N(C)C1=O

InChI Identifier

InChI=1S/C20H28N2O3S2/c1-14(2)11-12-25-16-9-7-15(8-10-16)13-20(27-6)19(24)21(3)18(26-5)17(23)22(20)4/h7-11,18H,12-13H2,1-6H3/t18-,20-/m0/s1

InChI Key

XBKBUMFBHNQOLC-ICSRJNTNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium solitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

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 acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Thiodioxopiperazine
Phenoxy compound
Dioxopiperazine
Phenol ether
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
N-methylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Piperazine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Ether
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Hemithioaminal
Thioether
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Carbonyl group
Organic oxide
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	3.97	ChemAxon
pKa (Strongest Acidic)	16.04	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.5 m³·mol⁻¹	ChemAxon
Polarizability	43.63 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

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

13877561

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione (NP0219362)

MOL for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

3D MOL for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

3D SDF for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

3D-SDF for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

PDB for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

3D PDB for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

SMILES for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

INCHI for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

Structure for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)

3D Structure for NP0219362 ((3s,6s)-1,4-dimethyl-3-({4-[(3-methylbut-2-en-1-yl)oxy]phenyl}methyl)-3,6-bis(methylsulfanyl)piperazine-2,5-dione)