MiMeDB: Showing metabocard for Rubrofusarin-6-O-Î±-D-ribofuranoside (MMDBc0016444)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:06:13 UTC

Update Date

2022-08-31 06:41:01 UTC

Metabolite ID

MMDBc0016444

Metabolite Identification

Common Name

Rubrofusarin-6-O-Î±-D-ribofuranoside

Description

Rubrofusarin-6-O-alpha-D-ribofuranoside belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. Based on a literature review very few articles have been published on Rubrofusarin-6-O-alpha-D-ribofuranoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109062D          

 33 36  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6985    3.9038    0.0000 C   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
    2.1434    1.2375    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
    0.0000    2.4750    0.0000 C   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781    3.9900    0.0000 C   0  0  2  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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    4.7045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586    4.5330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1835    4.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8011    5.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455    5.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260    3.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274    4.6819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    5.3457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    4.2373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.8886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  1  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21  7  1  0  0  0  0
 22 11  2  0  0  0  0
 17 23  1  6  0  0  0
 24 18  1  0  0  0  0
 19 25  1  6  0  0  0
 26  2  1  0  0  0  0
 26 10  1  0  0  0  0
 27  8  1  0  0  0  0
 27 12  1  0  0  0  0
 28 13  1  0  0  0  0
 20 28  1  6  0  0  0
 29 14  1  0  0  0  0
 29 20  1  0  0  0  0
 14 30  1  6  0  0  0
 17 31  1  1  0  0  0
 19 32  1  1  0  0  0
 20 33  1  1  0  0  0
M  END


  Mrv1652305152109062D          

 33 36  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6985    3.9038    0.0000 C   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
    2.1434    1.2375    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
    0.0000    2.4750    0.0000 C   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781    3.9900    0.0000 C   0  0  2  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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    4.7045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586    4.5330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1835    4.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8011    5.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455    5.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260    3.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274    4.6819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    5.3457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    4.2373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.8886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  1  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21  7  1  0  0  0  0
 22 11  2  0  0  0  0
 17 23  1  6  0  0  0
 24 18  1  0  0  0  0
 19 25  1  6  0  0  0
 26  2  1  0  0  0  0
 26 10  1  0  0  0  0
 27  8  1  0  0  0  0
 27 12  1  0  0  0  0
 28 13  1  0  0  0  0
 20 28  1  6  0  0  0
 29 14  1  0  0  0  0
 29 20  1  0  0  0  0
 14 30  1  6  0  0  0
 17 31  1  1  0  0  0
 19 32  1  1  0  0  0
 20 33  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016444

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(CO)O[C@]([H])(OC2=C3C(O)=C4C(=O)C=C(C)OC4=CC3=CC(OC)=C2)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O9/c1-8-3-11(22)16-12(27-8)5-9-4-10(26-2)6-13(15(9)18(16)24)28-20-19(25)17(23)14(7-21)29-20/h3-6,14,17,19-21,23-25H,7H2,1-2H3/t14-,17-,19-,20+/m1/s1

> <INCHI_KEY>
SIZIWNVEXFRCBS-JRJVTICQSA-N

> <FORMULA>
C20H20O9

> <MOLECULAR_WEIGHT>
404.371

> <EXACT_MASS>
404.110732224

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.294541842602904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-8-methoxy-2-methyl-4H-benzo[g]chromen-4-one

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.108494965666667

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.264640413426575

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.790104223612367

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811523914790055

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
100.1643

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-8-methoxy-2-methylbenzo[g]chromen-4-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      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.637   7.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   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       9.106   7.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.336   8.782   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.829   8.462   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.542   8.533   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.962  10.189   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.685   9.492   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.075   6.304   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       9.944   8.740   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.367   9.979   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.392   7.910   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.749   5.392   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   26                                                            
CONECT    3    8   11                                                       
CONECT    4    9   10                                                       
CONECT    5    9   12                                                       
CONECT    6   10   13                                                       
CONECT    7   14   21                                                       
CONECT    8    1    3   27                                                  
CONECT    9    4    5   15                                                  
CONECT   10    4    6   26                                                  
CONECT   11    3   16   22                                                  
CONECT   12    5   16   27                                                  
CONECT   13    6   15   28                                                  
CONECT   14    7   17   29   30                                             
CONECT   15    9   13   18                                                  
CONECT   16   11   12   18                                                  
CONECT   17   14   19   23   31                                             
CONECT   18   15   16   24                                                  
CONECT   19   17   20   25   32                                             
CONECT   20   19   28   29   33                                             
CONECT   21    7                                                            
CONECT   22   11                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26    2   10                                                       
CONECT   27    8   12                                                       
CONECT   28   13   20                                                       
CONECT   29   14   20                                                       
CONECT   30   14                                                            
CONECT   31   17                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

Synonyms

Value	Source
Rubrofusarin-6-O-a-D-ribofuranoside	Generator
Rubrofusarin-6-O-α-D-ribofuranoside	Generator

Molecular Formula

C₂₀H₂₀O₉

Average Mass

404.371

Monoisotopic Mass

404.110732224

IUPAC Name

6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-8-methoxy-2-methyl-4H-benzo[g]chromen-4-one

Traditional Name

6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-8-methoxy-2-methylbenzo[g]chromen-4-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO)O[C@]([H])(OC2=C3C(O)=C4C(=O)C=C(C)OC4=CC3=CC(OC)=C2)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C20H20O9/c1-8-3-11(22)16-12(27-8)5-9-4-10(26-2)6-13(15(9)18(16)24)28-20-19(25)17(23)14(7-21)29-20/h3-6,14,17,19-21,23-25H,7H2,1-2H3/t14-,17-,19-,20+/m1/s1

InChI Key

SIZIWNVEXFRCBS-JRJVTICQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranone glycosides

Alternative Parents

Substituents

Naphthopyranone glycoside
Phenolic glycoside
Chromone
Glycosyl compound
1-naphthol
O-glycosyl compound
Benzopyran
Naphthalene
1-benzopyran
Pentose monosaccharide
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monosaccharide
Benzenoid
Pyran
Tetrahydrofuran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Acetal
Oxacycle
Ether
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Primary 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	0.74 g/L	ALOGPS
logP	0.98	ALOGPS
logP	1.11	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.16 m³·mol⁻¹	ChemAxon
Polarizability	40.29 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

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

78441396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587610

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 Rubrofusarin-6-O-Î±-D-ribofuranoside (MMDBc0016444)

MOL for #<Metabolite:0x00007f923126d480>

3D MOL for #<Metabolite:0x00007f923126d480>

3D SDF for #<Metabolite:0x00007f923126d480>

3D-SDF for #<Metabolite:0x00007f923126d480>

PDB for #<Metabolite:0x00007f923126d480>

3D PDB for #<Metabolite:0x00007f923126d480>

SMILES for #<Metabolite:0x00007f923126d480>

INCHI for #<Metabolite:0x00007f923126d480>

Structure for #<Metabolite:0x00007f923126d480>

3D Structure for #<Metabolite:0x00007f923126d480>