MiMeDB: Showing metabocard for Globosuxanthone B (MMDBc0011188)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:07:08 UTC

Update Date

2022-08-31 06:32:43 UTC

Metabolite ID

MMDBc0011188

Metabolite Identification

Common Name

Globosuxanthone B

Description

globosuxanthone B belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. globosuxanthone B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on globosuxanthone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152105072D          

 26 28  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0416    3.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    3.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    3.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    3.9031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  1  0  0  0
 17  7  1  0  0  0  0
 18 13  2  0  0  0  0
 14 19  1  1  0  0  0
 20 15  2  0  0  0  0
 16 21  1  6  0  0  0
 22  1  1  0  0  0  0
 10 22  1  6  0  0  0
 23  2  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24  9  1  0  0  0  0
 10 25  1  1  0  0  0
 14 26  1  6  0  0  0
M  END


  Mrv1652305152105072D          

 26 28  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0416    3.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    3.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    3.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    3.9031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  1  0  0  0
 17  7  1  0  0  0  0
 18 13  2  0  0  0  0
 14 19  1  1  0  0  0
 20 15  2  0  0  0  0
 16 21  1  6  0  0  0
 22  1  1  0  0  0  0
 10 22  1  6  0  0  0
 23  2  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24  9  1  0  0  0  0
 10 25  1  1  0  0  0
 14 26  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0011188

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC2=C(C(=O)C3=C(O)C=CC=C3O2)[C@](O)(C(=O)OC)[C@]1([H])O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c1-22-10-6-9-12(16(21,14(10)19)15(20)23-2)13(18)11-7(17)4-3-5-8(11)24-9/h3-5,10,14,17,19,21H,6H2,1-2H3/t10-,14+,16+/m0/s1

> <INCHI_KEY>
DKCFLWCWQILBFZ-DRZCJDIDSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.783093025221895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,3S)-1,2,8-trihydroxy-3-methoxy-9-oxo-2,3,4,9-tetrahydro-1H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.1586423243333342

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.567209785364108

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.390347086823242

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8038386705696423

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
80.6076

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,3S)-1,2,8-trihydroxy-3-methoxy-9-oxo-3,4-dihydro-2H-xanthene-1-carboxylate

> <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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.300   7.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944   5.980   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.405   6.033   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.390   5.980   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.760   7.286   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.334   5.390   0.000  0.00  0.00           H+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    4   11   17                                                  
CONECT    8    5   11   24                                                  
CONECT    9    6   12   24                                                  
CONECT   10    6   14   22   25                                             
CONECT   11    7    8   13                                                  
CONECT   12    9   13   16                                                  
CONECT   13   11   12   18                                                  
CONECT   14   10   16   19   26                                             
CONECT   15   16   20   23                                                  
CONECT   16   12   14   15   21                                             
CONECT   17    7                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22    1   10                                                       
CONECT   23    2   15                                                       
CONECT   24    8    9                                                       
CONECT   25   10                                                            
CONECT   26   14                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Synonyms

Value	Source
1R,2R,8-trihydroxy-3S*-methoxy-1,2,3,4-tetrahydroxanthenone-1-carboxylic acid ester	ChEBI
1R,2R,8-trihydroxy-3S*-methoxy-1,2,3,4-tetrahydroxanthenone-1-carboxylate ester	Generator

Molecular Formula

C₁₆H₁₆O₈

Average Mass

336.296

Monoisotopic Mass

336.084517475

IUPAC Name

methyl (1R,2R,3S)-1,2,8-trihydroxy-3-methoxy-9-oxo-2,3,4,9-tetrahydro-1H-xanthene-1-carboxylate

Traditional Name

methyl (1R,2R,3S)-1,2,8-trihydroxy-3-methoxy-9-oxo-3,4-dihydro-2H-xanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=C(C(=O)C3=C(O)C=CC=C3O2)[C@](O)(C(=O)OC)[C@]1([H])O)OC

InChI Identifier

InChI=1S/C16H16O8/c1-22-10-6-9-12(16(21,14(10)19)15(20)23-2)13(18)11-7(17)4-3-5-8(11)24-9/h3-5,10,14,17,19,21H,6H2,1-2H3/t10-,14+,16+/m0/s1

InChI Key

DKCFLWCWQILBFZ-DRZCJDIDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Hydroxy acid
Heteroaromatic compound
Vinylogous acid
Methyl ester
Tertiary alcohol
1,2-diol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Polyol
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:68713 )
ether (CHEBI:68713 )
methyl ester (CHEBI:68713 )
xanthones (CHEBI:68713 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	10.5 g/L	ALOGPS
logP	0.72	ALOGPS
logP	0.16	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.61 m³·mol⁻¹	ChemAxon
Polarizability	31.78 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

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	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

30785582

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71768066

PDB ID

Not Available

ChEBI ID

68713

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 Globosuxanthone B (MMDBc0011188)

MOL for #<Metabolite:0x00007f922c8c0d28>

3D MOL for #<Metabolite:0x00007f922c8c0d28>

3D SDF for #<Metabolite:0x00007f922c8c0d28>

3D-SDF for #<Metabolite:0x00007f922c8c0d28>

PDB for #<Metabolite:0x00007f922c8c0d28>

3D PDB for #<Metabolite:0x00007f922c8c0d28>

SMILES for #<Metabolite:0x00007f922c8c0d28>

INCHI for #<Metabolite:0x00007f922c8c0d28>

Structure for #<Metabolite:0x00007f922c8c0d28>

3D Structure for #<Metabolite:0x00007f922c8c0d28>