MiMeDB: Showing metabocard for Neoglucobrassicin (MMDBc0053507)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:26:38 UTC

Update Date

2024-04-30 20:49:28 UTC

Metabolite ID

MMDBc0053507

Metabolite Identification

Common Name

Neoglucobrassicin

Description

Neoglucobrassicin, also known as MIMG, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Outside of the human body, neoglucobrassicin has been detected, but not quantified in, several different foods, such as swedes, garden cress, Brussel sprouts, Chinese cabbages, and kohlrabis. This could make neoglucobrassicin a potential biomarker for the consumption of these foods. Neoglucobrassicin is widespread in Brassica species and found in the Cruciferae, Tovariaceae, Capparidaceae, and Resedaceae.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023472D          

 31 33  0  0  0  0            999 V2000
    1.4358    3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -3.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4509   -2.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -1.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -0.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350   -0.3332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -1.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302   -0.2722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20  8  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 27  1  1  0  0  0  0
 27 19  1  0  0  0  0
 28 12  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 13  1  0  0  0  0
 30 17  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  2  0  0  0  0
 31 26  2  0  0  0  0
 31 29  1  0  0  0  0
M  END


  Mrv1652306222023472D          

 31 33  0  0  0  0            999 V2000
    1.4358    3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -3.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4509   -2.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -1.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -0.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350   -0.3332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -1.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302   -0.2722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20  8  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 27  1  1  0  0  0  0
 27 19  1  0  0  0  0
 28 12  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 13  1  0  0  0  0
 30 17  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  2  0  0  0  0
 31 26  2  0  0  0  0
 31 29  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053507

> <DATABASE_NAME>
MIME

> <SMILES>
CON1C=C(C\C(SC2OC(CO)C(O)C(O)C2O)=N/OS(O)(=O)=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O10S2/c1-27-19-7-9(10-4-2-3-5-11(10)19)6-13(18-29-31(24,25)26)30-17-16(23)15(22)14(21)12(8-20)28-17/h2-5,7,12,14-17,20-23H,6,8H2,1H3,(H,24,25,26)/b18-13+

> <INCHI_KEY>
PKKMITFKYRCCOL-QGOAFFKASA-N

> <FORMULA>
C17H22N2O10S2

> <MOLECULAR_WEIGHT>
478.494

> <EXACT_MASS>
478.071586314

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
45.44860864209625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-[2-(1-methoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-1.04

> <JCHEM_LOGP>
-2.383309845407698

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447138728249943

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.5140521076486637

> <JCHEM_PKA_STRONGEST_BASIC>
-0.35294585737401885

> <JCHEM_POLAR_SURFACE_AREA>
180.26999999999998

> <JCHEM_REFRACTIVITY>
108.89109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-[2-(1-methoxyindol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       2.680   6.698   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.296  -5.910   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.772  -4.445   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.278  -4.125   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.754  -2.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.723  -1.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.217  -1.836   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.204  -2.477   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       6.326  -7.055   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.308  -5.270   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.260  -2.340   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.199  -0.052   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.812  -0.622   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.477  -2.683   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.363  -0.508   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.741  -3.301   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.698  -2.797   0.000  0.00  0.00           O+0
HETATM   30  S   UNK     0       4.187  -0.692   0.000  0.00  0.00           S+0
HETATM   31  S   UNK     0      -0.332  -1.653   0.000  0.00  0.00           S+0
CONECT    1   27                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   13                                                       
CONECT    7    9   19                                                       
CONECT    8   12   20                                                       
CONECT    9    6    7   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    5   10   19                                                  
CONECT   12    8   14   28                                                  
CONECT   13    6   18   30                                                  
CONECT   14   12   15   21                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   28   30                                                  
CONECT   18   13   29                                                       
CONECT   19    7   11   27                                                  
CONECT   20    8                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   31                                                            
CONECT   25   31                                                            
CONECT   26   31                                                            
CONECT   27    1   19                                                       
CONECT   28   12   17                                                       
CONECT   29   18   31                                                       
CONECT   30   13   17                                                       
CONECT   31   24   25   26   29                                             
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

Synonyms

Value	Source
1-Methoxy-3-indolylmethyl glucosinolate	HMDB
1-Methoxy-3-indolylmethylglucosinolate	HMDB
1-Methoxyindol-3-ylmethylglucosinolate	HMDB
MIMG	HMDB
N-Methoxyglucobrassicin	HMDB
NGBS CPD	MeSH

Molecular Formula

C₁₇H₂₂N₂O₁₀S₂

Average Mass

478.494

Monoisotopic Mass

478.071586314

IUPAC Name

{[(E)-[2-(1-methoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid

Traditional Name

[(E)-[2-(1-methoxyindol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

CON1C=C(C\C(SC2OC(CO)C(O)C(O)C2O)=N/OS(O)(=O)=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C17H22N2O10S2/c1-27-19-7-9(10-4-2-3-5-11(10)19)6-13(18-29-31(24,25)26)30-17-16(23)15(22)14(21)12(8-20)28-17/h2-5,7,12,14-17,20-23H,6,8H2,1H3,(H,24,25,26)/b18-13+

InChI Key

PKKMITFKYRCCOL-QGOAFFKASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
3-alkylindole
Indole
Indole or derivatives
Oxane
Benzenoid
Substituted pyrrole
Monothioacetal
Heteroaromatic compound
Organic sulfuric acid or derivatives
Pyrrole
Secondary alcohol
Oxacycle
Azacycle
Polyol
Organoheterocyclic compound
Sulfenyl compound
Organosulfur compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Organic oxide
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	2.31 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.4	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.27 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.89 m³·mol⁻¹	ChemAxon
Polarizability	45.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

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

HMDB0038384

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017734

KNApSAcK ID

C00000126

Chemspider ID

Not Available

KEGG Compound ID

C08424

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6828856

PDB ID

Not Available

ChEBI ID

27506

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Neoglucobrassicin (MMDBc0053507)

MOL for #<Metabolite:0x00007f91f5885ea8>

3D MOL for #<Metabolite:0x00007f91f5885ea8>

3D SDF for #<Metabolite:0x00007f91f5885ea8>

3D-SDF for #<Metabolite:0x00007f91f5885ea8>

PDB for #<Metabolite:0x00007f91f5885ea8>

3D PDB for #<Metabolite:0x00007f91f5885ea8>

SMILES for #<Metabolite:0x00007f91f5885ea8>

INCHI for #<Metabolite:0x00007f91f5885ea8>

Structure for #<Metabolite:0x00007f91f5885ea8>

3D Structure for #<Metabolite:0x00007f91f5885ea8>