MiMeDB: Showing metabocard for Bicoumanigrin (MMDBc0016036)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:45:54 UTC

Update Date

2022-08-31 06:40:17 UTC

Metabolite ID

MMDBc0016036

Metabolite Identification

Common Name

Bicoumanigrin

Description

4,7-dihydroxy-4',7'-dimethoxy-5,5'-dimethyl-2H,2'H-[3,3'-bichromene]-2,2'-dione belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 4,7-dihydroxy-4',7'-dimethoxy-5,5'-dimethyl-2H,2'H-[3,3'-bichromene]-2,2'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171516172D          

 30 33  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    0.0000   -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
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
   -2.1434    1.2375    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  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
   -0.7145    2.0625    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
    0.7145   -0.4125    0.0000 C   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  3 16  1  0  0  0  0
  8 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END


  Mrv1533004171516172D          

 30 33  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    0.0000   -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
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
   -2.1434    1.2375    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  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
   -0.7145    2.0625    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
    0.7145   -0.4125    0.0000 C   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  3 16  1  0  0  0  0
  8 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016036

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(C)=C2C(OC(=O)C(=C2OC)C2=C(O)C3=C(C)C=C(O)C=C3OC2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O8/c1-9-5-11(23)7-13-15(9)19(24)17(21(25)29-13)18-20(28-4)16-10(2)6-12(27-3)8-14(16)30-22(18)26/h5-8,23-24H,1-4H3

> <INCHI_KEY>
LESVQQSUHUNTRC-UHFFFAOYSA-N

> <FORMULA>
C22H18O8

> <MOLECULAR_WEIGHT>
410.378

> <EXACT_MASS>
410.10016754

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
41.047307236228775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4,7-dihydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethoxy-5-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.176296759333333

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.829432497474804

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.030256670980676

> <JCHEM_PKA_STRONGEST_BASIC>
-4.55444342076654

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
107.86949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4,7-dihydroxy-5-methyl-2-oxochromen-3-yl)-4,7-dimethoxy-5-methylchromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   1.540   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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    3    8                                                  
CONECT   17    4   18   29                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   17   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Synonyms

Value	Source
33'-Bicoumarin bicoumanigrin	ChEMBL

Molecular Formula

C₂₂H₁₈O₈

Average Mass

410.378

Monoisotopic Mass

410.10016754

IUPAC Name

3-(4,7-dihydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethoxy-5-methyl-2H-chromen-2-one

Traditional Name

3-(4,7-dihydroxy-5-methyl-2-oxochromen-3-yl)-4,7-dimethoxy-5-methylchromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C2C(OC(=O)C(=C2OC)C2=C(O)C3=C(C)C=C(O)C=C3OC2=O)=C1

InChI Identifier

InChI=1S/C22H18O8/c1-9-5-11(23)7-13-15(9)19(24)17(21(25)29-13)18-20(28-4)16-10(2)6-12(27-3)8-14(16)30-22(18)26/h5-8,23-24H,1-4H3

InChI Key

LESVQQSUHUNTRC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
7-hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	0.026 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.18	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	5.03	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.87 m³·mol⁻¹	ChemAxon
Polarizability	41.05 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

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

54704239

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 Bicoumanigrin (MMDBc0016036)

MOL for #<Metabolite:0x00007f92307bbac8>

3D MOL for #<Metabolite:0x00007f92307bbac8>

3D SDF for #<Metabolite:0x00007f92307bbac8>

3D-SDF for #<Metabolite:0x00007f92307bbac8>

PDB for #<Metabolite:0x00007f92307bbac8>

3D PDB for #<Metabolite:0x00007f92307bbac8>

SMILES for #<Metabolite:0x00007f92307bbac8>

INCHI for #<Metabolite:0x00007f92307bbac8>

Structure for #<Metabolite:0x00007f92307bbac8>

3D Structure for #<Metabolite:0x00007f92307bbac8>