MiMeDB: Showing metabocard for Terragine B (MMDBc0003245)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:22:23 UTC

Update Date

2022-08-31 06:20:37 UTC

Metabolite ID

MMDBc0003245

Metabolite Identification

Common Name

Terragine B

Description

N-[5-(2,5-dioxopyrrolidin-1-yl)pentyl]-N-hydroxy-2-phenylacetamide belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. N-[5-(2,5-dioxopyrrolidin-1-yl)pentyl]-N-hydroxy-2-phenylacetamide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241506502D          

 23 24  0  0  0  0            999 V2000
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -5.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -6.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232   -4.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -3.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427   -4.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -3.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   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  1  0  0  0  0
  4  5  1  0  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0003245

> <DATABASE_NAME>
MIME

> <SMILES>
ON(CCCCCN1C(=O)CCC1=O)C(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O4/c20-15-9-10-16(21)18(15)11-5-2-6-12-19(23)17(22)13-14-7-3-1-4-8-14/h1,3-4,7-8,23H,2,5-6,9-13H2

> <INCHI_KEY>
BIBKONJGMVYAQA-UHFFFAOYSA-N

> <FORMULA>
C17H22N2O4

> <MOLECULAR_WEIGHT>
318.373

> <EXACT_MASS>
318.157957196

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.677583905560084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[5-(2,5-dioxopyrrolidin-1-yl)pentyl]-N-hydroxy-2-phenylacetamide

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.1051164663333328

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.358263854149975

> <JCHEM_PKA_STRONGEST_BASIC>
-5.703895390194799

> <JCHEM_POLAR_SURFACE_AREA>
77.92

> <JCHEM_REFRACTIVITY>
85.16920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[5-(2,5-dioxopyrrolidin-1-yl)pentyl]-N-hydroxy-2-phenylacetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      10.669  -9.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.260  -9.866   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.940 -11.373   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.230  -8.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.000  -7.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.506  -7.708   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.651  -6.678   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Synonyms

Not Available

Molecular Formula

C₁₇H₂₂N₂O₄

Average Mass

318.373

Monoisotopic Mass

318.157957196

IUPAC Name

N-[5-(2,5-dioxopyrrolidin-1-yl)pentyl]-N-hydroxy-2-phenylacetamide

Traditional Name

N-[5-(2,5-dioxopyrrolidin-1-yl)pentyl]-N-hydroxy-2-phenylacetamide

CAS Registry Number

Not Available

SMILES

ON(CCCCCN1C(=O)CCC1=O)C(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H22N2O4/c20-15-9-10-16(21)18(15)11-5-2-6-12-19(23)17(22)13-14-7-3-1-4-8-14/h1,3-4,7-8,23H,2,5-6,9-13H2

InChI Key

BIBKONJGMVYAQA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
Carboxylic acid imide, n-substituted
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Carboxylic acid imide
Dicarboximide
Pyrrolidine
Hydroxamic acid
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.11	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.17 m³·mol⁻¹	ChemAxon
Polarizability	33.68 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

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

Not Available

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
Bacteria	Actinobacteria	1		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

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

102461360

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 Terragine B (MMDBc0003245)

MOL for #<Metabolite:0x00007fecf0012928>

3D MOL for #<Metabolite:0x00007fecf0012928>

3D SDF for #<Metabolite:0x00007fecf0012928>

3D-SDF for #<Metabolite:0x00007fecf0012928>

PDB for #<Metabolite:0x00007fecf0012928>

3D PDB for #<Metabolite:0x00007fecf0012928>

SMILES for #<Metabolite:0x00007fecf0012928>

INCHI for #<Metabolite:0x00007fecf0012928>

Structure for #<Metabolite:0x00007fecf0012928>

3D Structure for #<Metabolite:0x00007fecf0012928>