MiMeDB: Showing metabocard for 2-O-methylalternariol 4-O-Î²-[4-methoxyl-glucopyranoside] (MMDBc0017235)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:40:35 UTC

Update Date

2022-08-31 06:41:59 UTC

Metabolite ID

MMDBc0017235

Metabolite Identification

Common Name

2-O-methylalternariol 4-O-Î²-[4-methoxyl-glucopyranoside]

Description

2-O-methylalternariol 4-O-beta-[4-methoxyl-glucopyranoside] belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review very few articles have been published on 2-O-methylalternariol 4-O-beta-[4-methoxyl-glucopyranoside].

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109402D          

 32 35  0  0  0  0            999 V2000
    0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22 11  1  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 24  9  1  0  0  0  0
 25 12  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28 23  2  0  0  0  0
 29  2  1  0  0  0  0
 29 15  1  0  0  0  0
 30  3  1  0  0  0  0
 30 22  1  0  0  0  0
 31 13  1  0  0  0  0
 31 17  1  0  0  0  0
 32 16  1  0  0  0  0
 32 23  1  0  0  0  0
M  END


  Mrv1652305152109402D          

 32 35  0  0  0  0            999 V2000
    0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22 11  1  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 24  9  1  0  0  0  0
 25 12  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28 23  2  0  0  0  0
 29  2  1  0  0  0  0
 29 15  1  0  0  0  0
 30  3  1  0  0  0  0
 30 22  1  0  0  0  0
 31 13  1  0  0  0  0
 31 17  1  0  0  0  0
 32 16  1  0  0  0  0
 32 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0017235

> <DATABASE_NAME>
MIME

> <SMILES>
COC1C(CO)CC(OC2=CC3=C(C(=O)OC4=C3C(C)=CC(O)=C4)C(OC)=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O9/c1-10-4-12(25)6-16-18(10)14-7-13(8-15(29-2)19(14)23(28)32-16)31-17-5-11(9-24)22(30-3)21(27)20(17)26/h4,6-8,11,17,20-22,24-27H,5,9H2,1-3H3

> <INCHI_KEY>
PDRMBHJHPAWGEC-UHFFFAOYSA-N

> <FORMULA>
C23H26O9

> <MOLECULAR_WEIGHT>
446.452

> <EXACT_MASS>
446.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.69279878727447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-{[2,3-dihydroxy-5-(hydroxymethyl)-4-methoxycyclohexyl]oxy}-3-hydroxy-7-methoxy-1-methyl-6H-benzo[c]chromen-6-one

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.0073781286666663

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.827607556704383

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.715817015758647

> <JCHEM_PKA_STRONGEST_BASIC>
-2.632484014321249

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
113.03899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-{[2,3-dihydroxy-5-(hydroxymethyl)-4-methoxycyclohexyl]oxy}-3-hydroxy-7-methoxy-1-methylbenzo[c]chromen-6-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       1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.104   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.804  -3.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.056  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.056   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.874   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.494   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.826   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.104   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.516   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.746   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.564   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.206   3.437   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -9.034   0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.366   0.770   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -4.414  -4.565   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.494  -4.565   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.564   4.771   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.874   3.437   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -9.034  -1.897   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.746   3.437   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   29                                                            
CONECT    3   30                                                            
CONECT    4   10   12                                                       
CONECT    5   11   17                                                       
CONECT    6   12   16                                                       
CONECT    7   13   14                                                       
CONECT    8   13   15                                                       
CONECT    9   11   24                                                       
CONECT   10    1    4   18                                                  
CONECT   11    5    9   22                                                  
CONECT   12    4    6   25                                                  
CONECT   13    7    8   31                                                  
CONECT   14    7   18   19                                                  
CONECT   15    8   19   29                                                  
CONECT   16    6   18   32                                                  
CONECT   17    5   20   31                                                  
CONECT   18   10   14   16                                                  
CONECT   19   14   15   23                                                  
CONECT   20   17   21   26                                                  
CONECT   21   20   22   27                                                  
CONECT   22   11   21   30                                                  
CONECT   23   19   28   32                                                  
CONECT   24    9                                                            
CONECT   25   12                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   23                                                            
CONECT   29    2   15                                                       
CONECT   30    3   22                                                       
CONECT   31   13   17                                                       
CONECT   32   16   23                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Synonyms

Value	Source
2-O-Methylalternariol 4-O-b-[4-methoxyl-glucopyranoside]	Generator
2-O-Methylalternariol 4-O-β-[4-methoxyl-glucopyranoside]	Generator
2-O-Methylalternariol 4-O-beta-(4-methoxyl-glucopyranoside)	MeSH

Molecular Formula

C₂₃H₂₆O₉

Average Mass

446.452

Monoisotopic Mass

446.157682417

IUPAC Name

9-{[2,3-dihydroxy-5-(hydroxymethyl)-4-methoxycyclohexyl]oxy}-3-hydroxy-7-methoxy-1-methyl-6H-benzo[c]chromen-6-one

Traditional Name

9-{[2,3-dihydroxy-5-(hydroxymethyl)-4-methoxycyclohexyl]oxy}-3-hydroxy-7-methoxy-1-methylbenzo[c]chromen-6-one

CAS Registry Number

Not Available

SMILES

COC1C(CO)CC(OC2=CC3=C(C(=O)OC4=C3C(C)=CC(O)=C4)C(OC)=C2)C(O)C1O

InChI Identifier

InChI=1S/C23H26O9/c1-10-4-12(25)6-16-18(10)14-7-13(8-15(29-2)19(14)23(28)32-16)31-17-5-11(9-24)22(30-3)21(27)20(17)26/h4,6-8,11,17,20-22,24-27H,5,9H2,1-3H3

InChI Key

PDRMBHJHPAWGEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Coumarin
2-benzopyran
1-benzopyran
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Cyclohexanol
Alkyl aryl ether
Benzenoid
Pyran
Cyclitol or derivatives
Heteroaromatic compound
Vinylogous ester
Cyclic alcohol
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	0.27 g/L	ALOGPS
logP	1.49	ALOGPS
logP	1.01	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.04 m³·mol⁻¹	ChemAxon
Polarizability	45.69 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

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	2	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

78444693

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587853

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 2-O-methylalternariol 4-O-Î²-[4-methoxyl-glucopyranoside] (MMDBc0017235)

MOL for #<Metabolite:0x00007f1241117ad8>

3D MOL for #<Metabolite:0x00007f1241117ad8>

3D SDF for #<Metabolite:0x00007f1241117ad8>

3D-SDF for #<Metabolite:0x00007f1241117ad8>

PDB for #<Metabolite:0x00007f1241117ad8>

3D PDB for #<Metabolite:0x00007f1241117ad8>

SMILES for #<Metabolite:0x00007f1241117ad8>

INCHI for #<Metabolite:0x00007f1241117ad8>

Structure for #<Metabolite:0x00007f1241117ad8>

3D Structure for #<Metabolite:0x00007f1241117ad8>