MiMeDB: Showing metabocard for 1'-(2-phenyl-ethylene)-ditryptophenaline (MMDBc0016065)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:47:23 UTC

Update Date

2025-10-07 16:06:30 UTC

Metabolite ID

MMDBc0016065

Metabolite Identification

Common Name

1'-(2-phenyl-ethylene)-ditryptophenaline

Description

1'-(2-phenyl-ethylene)-ditryptophenaline is a dimeric diketopiperazine, a class of compounds characterized by their cyclic structure formed from two amino acids. This compound was isolated from the fungus Aspergillus flavus, where it was found alongside another diketopiperazine, ditryptophenaline (PMID:7528269 ). The chemical structure of 1'-(2-phenyl-ethylene)-ditryptophenaline features a unique phenyl-ethylene moiety that contributes to its distinct properties and biological interactions. Diketopiperazines are known for their diverse biological activities, including potential roles in signaling pathways and interactions with various biological targets, although the specific pathways involving 1'-(2-phenyl-ethylene)-ditryptophenaline remain to be fully elucidated. The presence of such metabolites in fungi like Aspergillus flavus suggests their involvement in ecological interactions or defense mechanisms, potentially impacting microbial competition and survival. Further research into this compound may reveal additional insights into its chemical behavior and biological implications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108472D          

 62 72  0  0  0  0            999 V2000
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M  END


  Mrv1652305152108472D          

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M  END
> <DATABASE_ID>
MMDBc0016065

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC=CC=C1)N1C2N3C(CC2(C2=CC=CC=C12)C12CC4N(C1NC1=CC=CC=C21)C(=O)C(CC1=CC=CC=C1)N(C)C4=O)C(=O)N(C)C(CC1=CC=CC=C1)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C50H46N6O4/c1-52-39(28-33-18-8-4-9-19-33)45(59)55-41(43(52)57)30-49(35-22-12-14-24-37(35)51-47(49)55)50-31-42-44(58)53(2)40(29-34-20-10-5-11-21-34)46(60)56(42)48(50)54(38-25-15-13-23-36(38)50)27-26-32-16-6-3-7-17-32/h3-27,39-42,47-48,51H,28-31H2,1-2H3/b27-26+

> <INCHI_KEY>
JFPDNRWQLIIEKO-CYYJNZCTSA-N

> <FORMULA>
C50H46N6O4

> <MOLECULAR_WEIGHT>
794.956

> <EXACT_MASS>
794.358053985

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
84.71698161636985

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-benzyl-9-{4-benzyl-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl}-5-methyl-16-[(E)-2-phenylethenyl]-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
6.557293705333334

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.336671195965444

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.154121318736113

> <JCHEM_PKA_STRONGEST_BASIC>
2.1108758281668596

> <JCHEM_POLAR_SURFACE_AREA>
96.50999999999999

> <JCHEM_REFRACTIVITY>
230.14470000000017

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-benzyl-9-{4-benzyl-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl}-5-methyl-16-[(E)-2-phenylethenyl]-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      11.873   3.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.623   2.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.882  -7.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.644   5.464   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.065   1.634   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.410  -6.852   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.953  -5.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.340   6.974   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.488   4.446   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.909   0.101   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.816   2.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.299   4.008   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.170   2.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.996   5.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.594   1.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.010  -5.433   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.553  -4.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.881   7.466   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.029   4.938   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.505  -0.530   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.411   1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.759   3.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.711   3.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.031   6.354   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.438   0.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.681  -2.786   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.704  -1.492   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.266   6.940   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.774  -0.296   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.457   3.131   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.013   3.688   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.081  -4.205   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.725   6.448   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.256   0.371   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.794   4.352   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.675   2.467   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.490   5.862   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.979   0.957   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.110   5.922   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.359   0.897   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.799   3.887   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.671   2.932   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.258   3.395   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.211   3.424   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.651   6.414   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.819   0.405   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.965   5.574   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.504   1.245   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.324   4.174   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.146   2.645   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0       4.832   6.617   0.000  0.00  0.00           N+0
HETATM   52  N   UNK     0      10.414   4.413   0.000  0.00  0.00           N+0
HETATM   53  N   UNK     0       0.056   2.406   0.000  0.00  0.00           N+0
HETATM   54  N   UNK     0       5.637   0.202   0.000  0.00  0.00           N+0
HETATM   55  N   UNK     0       7.495   5.396   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0       2.974   1.423   0.000  0.00  0.00           N+0
HETATM   57  O   UNK     0      10.013   2.053   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.443   4.914   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       8.347   7.924   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       1.937  -1.237   0.000  0.00  0.00           O+0
HETATM   61  H   UNK     0       8.209  -2.596   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.253  -2.011   0.000  0.00  0.00           H+0
CONECT    1   52                                                            
CONECT    2   53                                                            
CONECT    3    6    7                                                       
CONECT    4    8    9                                                       
CONECT    5   10   11                                                       
CONECT    6    3   16                                                       
CONECT    7    3   17                                                       
CONECT    8    4   18                                                       
CONECT    9    4   19                                                       
CONECT   10    5   20                                                       
CONECT   11    5   21                                                       
CONECT   12   14   22                                                       
CONECT   13   15   23                                                       
CONECT   14   12   24                                                       
CONECT   15   13   25                                                       
CONECT   16    6   32                                                       
CONECT   17    7   32                                                       
CONECT   18    8   33                                                       
CONECT   19    9   33                                                       
CONECT   20   10   34                                                       
CONECT   21   11   34                                                       
CONECT   22   12   35                                                       
CONECT   23   13   36                                                       
CONECT   24   14   37                                                       
CONECT   25   15   38                                                       
CONECT   26   27   32   61                                                  
CONECT   27   26   54   62                                                  
CONECT   28   33   39                                                       
CONECT   29   34   40                                                       
CONECT   30   41   49                                                       
CONECT   31   42   50                                                       
CONECT   32   16   17   26                                                  
CONECT   33   18   19   28                                                  
CONECT   34   20   21   29                                                  
CONECT   35   22   37   49                                                  
CONECT   36   23   38   50                                                  
CONECT   37   24   35   51                                                  
CONECT   38   25   36   54                                                  
CONECT   39   28   45   52                                                  
CONECT   40   29   46   53                                                  
CONECT   41   30   43   55                                                  
CONECT   42   31   44   56                                                  
CONECT   43   41   52   57                                                  
CONECT   44   42   53   58                                                  
CONECT   45   39   55   59                                                  
CONECT   46   40   56   60                                                  
CONECT   47   49   51   55                                                  
CONECT   48   50   54   56                                                  
CONECT   49   30   35   47   50                                             
CONECT   50   31   36   48   49                                             
CONECT   51   37   47                                                       
CONECT   52    1   39   43                                                  
CONECT   53    2   40   44                                                  
CONECT   54   27   38   48                                                  
CONECT   55   41   45   47                                                  
CONECT   56   42   46   48                                                  
CONECT   57   43                                                            
CONECT   58   44                                                            
CONECT   59   45                                                            
CONECT   60   46                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  144    0
END

Synonyms

Not Available

Molecular Formula

C₅₀H₄₆N₆O₄

Average Mass

794.956

Monoisotopic Mass

794.358053985

IUPAC Name

4-benzyl-9-{4-benzyl-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl}-5-methyl-16-[(E)-2-phenylethenyl]-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1)N1C2N3C(CC2(C2=CC=CC=C12)C12CC4N(C1NC1=CC=CC=C21)C(=O)C(CC1=CC=CC=C1)N(C)C4=O)C(=O)N(C)C(CC1=CC=CC=C1)C3=O

InChI Identifier

InChI=1S/C50H46N6O4/c1-52-39(28-33-18-8-4-9-19-33)45(59)55-41(43(52)57)30-49(35-22-12-14-24-37(35)51-47(49)55)50-31-42-44(58)53(2)40(29-34-20-10-5-11-21-34)46(60)56(42)48(50)54(38-25-15-13-23-36(38)50)27-26-32-16-6-3-7-17-32/h3-27,39-42,47-48,51H,28-31H2,1-2H3/b27-26+

InChI Key

JFPDNRWQLIIEKO-CYYJNZCTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
Styrene
Secondary aliphatic/aromatic amine
N-alkylpiperazine
N-methylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Amino acid or derivatives
Lactam
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid derivative
Enamine
Hydrocarbon derivative
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0046 g/L	ALOGPS
logP	5.11	ALOGPS
logP	6.56	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	2.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	96.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	230.14 m³·mol⁻¹	ChemAxon
Polarizability	84.72 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587509

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 1'-(2-phenyl-ethylene)-ditryptophenaline (MMDBc0016065)

MOL for #<Metabolite:0x00007f8de8b46c48>

3D MOL for #<Metabolite:0x00007f8de8b46c48>

3D SDF for #<Metabolite:0x00007f8de8b46c48>

3D-SDF for #<Metabolite:0x00007f8de8b46c48>

PDB for #<Metabolite:0x00007f8de8b46c48>

3D PDB for #<Metabolite:0x00007f8de8b46c48>

SMILES for #<Metabolite:0x00007f8de8b46c48>

INCHI for #<Metabolite:0x00007f8de8b46c48>

Structure for #<Metabolite:0x00007f8de8b46c48>

3D Structure for #<Metabolite:0x00007f8de8b46c48>