MiMeDB: Showing metabocard for Gillusdin (MMDBc0019148)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:15:39 UTC

Update Date

2022-08-31 06:44:56 UTC

Metabolite ID

MMDBc0019148

Metabolite Identification

Common Name

Gillusdin

Description

methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251504042D          

 27 29  0  0  0  0            999 V2000
    3.3996    3.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7949    2.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    2.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -1.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4121   -1.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -1.1491    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105   -0.3281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572    1.2631    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2831    2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790    1.9573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5609   -0.9379    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 27  1  0  0  0  0
M  END


  Mrv1533004251504042D          

 27 29  0  0  0  0            999 V2000
    3.3996    3.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7949    2.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    2.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -1.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4121   -1.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -1.1491    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105   -0.3281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572    1.2631    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2831    2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790    1.9573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5609   -0.9379    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 27  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019148

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)C1=CC(=O)C(O)=C(OC)C11OC2=C(Cl)C(O)=C(Cl)C(C)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H12Cl2O8/c1-5-8-13(10(19)12(22)9(5)18)27-17(14(8)23)6(16(24)26-3)4-7(20)11(21)15(17)25-2/h4,21-22H,1-3H3

> <INCHI_KEY>
GKDPVOBYIGAJSD-UHFFFAOYSA-N

> <FORMULA>
C17H12Cl2O8

> <MOLECULAR_WEIGHT>
415.18

> <EXACT_MASS>
413.9909227

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
37.04678412336175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.385762435666667

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.983824168529143

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.907666609472645

> <JCHEM_PKA_STRONGEST_BASIC>
-4.688531783714116

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000003

> <JCHEM_REFRACTIVITY>
95.94979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxospiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       6.346   6.490   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.084   5.138   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.244   3.761   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.870   4.448   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.807   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.693   0.661   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.807  -0.564   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.708  -2.223   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.369  -3.694   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.132  -0.476   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       0.546  -2.145   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.513  -0.613   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      -1.413   2.358   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.528   3.743   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.881   3.654   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.514  -1.751   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    5   14   25                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24   13   26                                                  
CONECT   26   25                                                            
CONECT   27    9                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Synonyms

Value	Source
Methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylic acid	Generator
5,7-Dichloro-5',6'-dihydroxy-6'-methoxy-4-methyl-3,4-dioxospiro(benzofuran-2(3H)-1'-(2,5)-cyclohexadiene)-2-carboxylic acid methyl ester	MeSH

Molecular Formula

C₁₇H₁₂Cl₂O₈

Average Mass

415.18

Monoisotopic Mass

413.9909227

IUPAC Name

methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

Traditional Name

methyl 5,7-dichloro-3',6-dihydroxy-2'-methoxy-4-methyl-3,4'-dioxospiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(=O)C(O)=C(OC)C11OC2=C(Cl)C(O)=C(Cl)C(C)=C2C1=O

InChI Identifier

InChI=1S/C17H12Cl2O8/c1-5-8-13(10(19)12(22)9(5)18)27-17(14(8)23)6(16(24)26-3)4-7(20)11(21)15(17)25-2/h4,21-22H,1-3H3

InChI Key

GKDPVOBYIGAJSD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Aryl chloride
Aryl halide
Benzenoid
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Cyclic ketone
Carboxylic acid ester
Ketone
Oxacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Organochloride
Hydrocarbon derivative
Organohalogen 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	0.046 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.39	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.91	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.95 m³·mol⁻¹	ChemAxon
Polarizability	37.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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

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

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

Not Available

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 Gillusdin (MMDBc0019148)

MOL for #<Metabolite:0x0000560bdf3c3b38>

3D MOL for #<Metabolite:0x0000560bdf3c3b38>

3D SDF for #<Metabolite:0x0000560bdf3c3b38>

3D-SDF for #<Metabolite:0x0000560bdf3c3b38>

PDB for #<Metabolite:0x0000560bdf3c3b38>

3D PDB for #<Metabolite:0x0000560bdf3c3b38>

SMILES for #<Metabolite:0x0000560bdf3c3b38>

INCHI for #<Metabolite:0x0000560bdf3c3b38>

Structure for #<Metabolite:0x0000560bdf3c3b38>

3D Structure for #<Metabolite:0x0000560bdf3c3b38>