MiMeDB: Showing metabocard for Astringin (MMDBc0033596)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:55:07 UTC

Update Date

2022-08-31 22:36:57 UTC

Metabolite ID

MMDBc0033596

Metabolite Identification

Common Name

Astringin

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007392D          

 29 31  0  0  0  0            999 V2000
 9988.5438 9990.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4056 9990.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1200 9990.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5529 9992.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9817 9991.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9743 9987.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1133 9987.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3981 9987.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1133 9991.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6829 9990.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6829 9988.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1133 9990.4731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9986.3988 9990.0606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9986.3988 9989.2356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.1133 9988.8232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9987.8277 9989.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.8277 9990.0606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.9741 9990.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2597 9990.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2597 9989.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9741 9988.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6886 9989.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6886 9990.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2654 9991.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5509 9991.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8365 9991.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8364 9990.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5508 9990.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2654 9990.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  1  1  6  0  0  0
 15  7  1  6  0  0  0
 14 11  1  1  0  0  0
 13 10  1  6  0  0  0
 12  9  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 24  1  0  0  0  0
  3 27  1  0  0  0  0
 25  4  1  0  0  0  0
 24  5  1  0  0  0  0
  1 19  1  0  0  0  0
 23  2  1  0  0  0  0
 21  6  1  0  0  0  0
M  END


  Mrv1652309272007392D          

 29 31  0  0  0  0            999 V2000
 9988.5438 9990.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4056 9990.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1200 9990.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5529 9992.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9817 9991.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9743 9987.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1133 9987.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3981 9987.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1133 9991.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6829 9990.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6829 9988.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1133 9990.4731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9986.3988 9990.0606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9986.3988 9989.2356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.1133 9988.8232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9987.8277 9989.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.8277 9990.0606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.9741 9990.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2597 9990.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2597 9989.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9741 9988.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6886 9989.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6886 9990.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2654 9991.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5509 9991.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8365 9991.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8364 9990.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5508 9990.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2654 9990.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  1  1  6  0  0  0
 15  7  1  6  0  0  0
 14 11  1  1  0  0  0
 13 10  1  6  0  0  0
 12  9  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 24  1  0  0  0  0
  3 27  1  0  0  0  0
 25  4  1  0  0  0  0
 24  5  1  0  0  0  0
  1 19  1  0  0  0  0
 23  2  1  0  0  0  0
 21  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033596

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(\C=C\C3=CC(O)=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
PERPNFLGJXUDDW-CUYWLFDKSA-N

> <FORMULA>
C20H22O9

> <MOLECULAR_WEIGHT>
406.387

> <EXACT_MASS>
406.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.838151086985405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.8307574713333334

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.096600192142327

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.492505059442484

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343730565

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
101.58080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
astringin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8645.2828648.882   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8650.6248648.882   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8651.9578648.115   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8654.6328652.740   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8657.2998651.198   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8647.9528644.259   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8642.6128644.259   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8641.2768643.490   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8642.6128650.424   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8639.9418648.882   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8639.9418645.800   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8642.6128648.883   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8641.2788648.113   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8641.2788646.573   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8642.6128645.803   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8643.9458646.573   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8643.9458648.113   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8647.9528648.883   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8646.6188648.113   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8646.6188646.573   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8647.9528645.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8649.2858646.573   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8649.2858648.113   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8655.9628650.424   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8654.6288651.194   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8653.2958650.424   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8653.2958648.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8654.6288648.114   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8655.9628648.884   0.000  0.00  0.00           C+0
CONECT    1   17   19                                                       
CONECT    2    3   23                                                       
CONECT    3    2   27                                                       
CONECT    4   25                                                            
CONECT    5   24                                                            
CONECT    6   21                                                            
CONECT    7    8   15                                                       
CONECT    8    7                                                            
CONECT    9   12                                                            
CONECT   10   13                                                            
CONECT   11   14                                                            
CONECT   12   13   17    9                                                  
CONECT   13   12   14   10                                                  
CONECT   14   13   15   11                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16    1                                                  
CONECT   18   19   23                                                       
CONECT   19   18   20    1                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    6                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18    2                                                  
CONECT   24   25   29    5                                                  
CONECT   25   24   26    4                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28    3                                                  
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

Synonyms

Value	Source
(e)-Astringin	ChEBI
3,4,3',5'-Tetrahydroxystilbene 3'-glucoside	ChEBI
Piceatannol 3-beta-D-glucoside	ChEBI
Piceatannol 3-beta-glucoside	ChEBI
Piceatannol 3-O-beta-D-glucoside	ChEBI
Piceatannol 3-b-D-glucoside	Generator
Piceatannol 3-β-D-glucoside	Generator
Piceatannol 3-b-glucoside	Generator
Piceatannol 3-β-glucoside	Generator
Piceatannol 3-O-b-D-glucoside	Generator
Piceatannol 3-O-β-D-glucoside	Generator
trans-Astringin	MeSH
3-[(1E)-2-(3,4-Dihydroxyphenyl)ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside	PhytoBank
3-[(1E)-2-(3,4-Dihydroxyphenyl)ethenyl]-5-hydroxyphenyl β-D-glucopyranoside	PhytoBank
3,4,3’,5’-Tetrahydroxystilbene 3’-glucoside	PhytoBank

Molecular Formula

C₂₀H₂₂O₉

Average Mass

406.387

Monoisotopic Mass

406.126382288

IUPAC Name

(2S,3R,4S,5S,6R)-2-{3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

astringin

CAS Registry Number

29884-49-9

SMILES

OC[C@H]1O[C@@H](OC2=CC(\C=C\C3=CC(O)=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

InChI Key

PERPNFLGJXUDDW-CUYWLFDKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Phenoxy compound
Phenol ether
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:2899 )
monosaccharide derivative (CHEBI:2899 )
polyphenol (CHEBI:2899 )
stilbenoid (CHEBI:2899 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10245 )
Stilbenes (C10245 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090007 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.83	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.58 m³·mol⁻¹	ChemAxon
Polarizability	40.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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	Unknown

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

C00002870

Chemspider ID

Not Available

KEGG Compound ID

C10245

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Astringin

METLIN ID

Not Available

PubChem Compound

5281712

PDB ID

Not Available

ChEBI ID

2899

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for Astringin (MMDBc0033596)

MOL for #<Metabolite:0x00007f121c1d0f80>

3D MOL for #<Metabolite:0x00007f121c1d0f80>

3D SDF for #<Metabolite:0x00007f121c1d0f80>

3D-SDF for #<Metabolite:0x00007f121c1d0f80>

PDB for #<Metabolite:0x00007f121c1d0f80>

3D PDB for #<Metabolite:0x00007f121c1d0f80>

SMILES for #<Metabolite:0x00007f121c1d0f80>

INCHI for #<Metabolite:0x00007f121c1d0f80>

Structure for #<Metabolite:0x00007f121c1d0f80>

3D Structure for #<Metabolite:0x00007f121c1d0f80>