MiMeDB: Showing metabocard for Deoxybrevianamide E (MMDBc0017250)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:41:10 UTC

Update Date

2024-10-17 16:54:58 UTC

Metabolite ID

MMDBc0017250

Metabolite Identification

Common Name

Deoxybrevianamide E

Description

Deoxybrevianamide E 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. Based on a literature review a small amount of articles have been published on Deoxybrevianamide E.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109412D          

 28 31  0  0  1  0            999 V2000
    7.3037    3.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5406    2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    2.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1760    1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.5475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  6  0  0  0
 17 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21 18  1  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  2  0  0  0  0
 24 11  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  2  0  0  0  0
 16 27  1  1  0  0  0
 17 28  1  1  0  0  0
M  END


  Mrv1652305152109412D          

 28 31  0  0  1  0            999 V2000
    7.3037    3.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5406    2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    2.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1760    1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.5475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  6  0  0  0
 17 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21 18  1  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  2  0  0  0  0
 24 11  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  2  0  0  0  0
 16 27  1  1  0  0  0
 17 28  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0017250

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=C(NC3=CC=CC=C13)C(C)(C)C=C)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C21H25N3O2/c1-4-21(2,3)18-14(13-8-5-6-9-15(13)22-18)12-16-20(26)24-11-7-10-17(24)19(25)23-16/h4-6,8-9,16-17,22H,1,7,10-12H2,2-3H3,(H,23,25)/t16-,17-/m0/s1

> <INCHI_KEY>
KUGNSEAHJVSMAJ-IRXDYDNUSA-N

> <FORMULA>
C21H25N3O2

> <MOLECULAR_WEIGHT>
351.45

> <EXACT_MASS>
351.194677057

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.76125808685311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.379958143666667

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.496210738549216

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.850726019846283

> <JCHEM_PKA_STRONGEST_BASIC>
1.5178263049518197

> <JCHEM_POLAR_SURFACE_AREA>
68.69

> <JCHEM_REFRACTIVITY>
101.6996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <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      13.634   5.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.342   3.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.355   3.353   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.169   5.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.728  -2.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.234  -2.921   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.252  -1.136   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.265  -1.776   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.283   0.008   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.789  -0.312   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.529   2.166   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.849   3.673   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      12.559   1.022   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       7.454   3.080   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.626  -1.532   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4    1   21                                                       
CONECT    5    6    8                                                       
CONECT    6    5    9                                                       
CONECT    7   10   11                                                       
CONECT    8    5   13                                                       
CONECT    9    6   15                                                       
CONECT   10    7   17                                                       
CONECT   11    7   24                                                       
CONECT   12   14   16                                                       
CONECT   13    8   14   15                                                  
CONECT   14   12   13   18                                                  
CONECT   15    9   13   22                                                  
CONECT   16   12   20   23   27                                             
CONECT   17   10   19   24   28                                             
CONECT   18   14   21   22                                                  
CONECT   19   17   23   25                                                  
CONECT   20   16   24   26                                                  
CONECT   21    2    3    4   18                                             
CONECT   22   15   18                                                       
CONECT   23   16   19                                                       
CONECT   24   11   17   20                                                  
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

Synonyms

Value	Source
Cyclo-2-(1,1-dimethylallyl)-L-tryptophyl-L-proline	ChEBI
Cyclo-L-prolyl-2-(1,1-dimethylallyl)-L-tryptophan	ChEBI
L-Prolyl-2-(1,1-dimethylallyl)-L-tryptophan anhydride	ChEBI

Molecular Formula

C₂₁H₂₅N₃O₂

Average Mass

351.45

Monoisotopic Mass

351.194677057

IUPAC Name

(3S,8aS)-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

Traditional Name

(3S,8aS)-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=C(NC3=CC=CC=C13)C(C)(C)C=C)N=C2O

InChI Identifier

InChI=1S/C21H25N3O2/c1-4-21(2,3)18-14(13-8-5-6-9-15(13)22-18)12-16-20(26)24-11-7-10-17(24)19(25)23-16/h4-6,8-9,16-17,22H,1,7,10-12H2,2-3H3,(H,23,25)/t16-,17-/m0/s1

InChI Key

KUGNSEAHJVSMAJ-IRXDYDNUSA-N

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
3-alkylindole
Indole
Indole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:72948 )
dipeptide (CHEBI:72948 )
indole alkaloid (CHEBI:72948 )
pyrrolopyrazine (CHEBI:72948 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.29	ALOGPS
logP	3.38	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.7 m³·mol⁻¹	ChemAxon
Polarizability	38.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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

Metabolic Reactions

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	6	Human feces; Human sputum; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

C00011277

Chemspider ID

158467

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182203

PDB ID

Not Available

ChEBI ID

72948

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Deoxybrevianamide E (MMDBc0017250)

MOL for #<Metabolite:0x00007fab2c9002e8>

3D MOL for #<Metabolite:0x00007fab2c9002e8>

3D SDF for #<Metabolite:0x00007fab2c9002e8>

3D-SDF for #<Metabolite:0x00007fab2c9002e8>

PDB for #<Metabolite:0x00007fab2c9002e8>

3D PDB for #<Metabolite:0x00007fab2c9002e8>

SMILES for #<Metabolite:0x00007fab2c9002e8>

INCHI for #<Metabolite:0x00007fab2c9002e8>

Structure for #<Metabolite:0x00007fab2c9002e8>

3D Structure for #<Metabolite:0x00007fab2c9002e8>