MiMeDB: Showing metabocard for (3S)-versiconol acetic acid (MMDBc0054936)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:38:09 UTC

Update Date

2022-08-12 20:09:09 UTC

Metabolite ID

MMDBc0054936

Metabolite Identification

Common Name

(3S)-versiconol acetic acid

Description

(3S)-versiconol acetate(1-), also known as (3S)-versiconol acetic acid, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Based on a literature review very few articles have been published on (3S)-versiconol acetate(1-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221382D          

 30 32  0  0  1  0            999 V2000
    3.7638    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    7.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3013    7.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    8.4927    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.2388    7.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388    5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  1  0  0  0
  9  7  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  2  0  0  0  0
 13  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  2  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  2  0  0  0  0
 23 10  1  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 18  2  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29  3  1  0  0  0  0
 29  8  1  0  0  0  0
  9 30  1  6  0  0  0
M  CHG  1  23  -1
M  END


  Mrv1652306172221382D          

 30 32  0  0  1  0            999 V2000
    3.7638    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    7.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3013    7.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    8.4927    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.2388    7.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388    5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  1  0  0  0
  9  7  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  2  0  0  0  0
 13  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  2  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  2  0  0  0  0
 23 10  1  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 18  2  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29  3  1  0  0  0  0
 29  8  1  0  0  0  0
  9 30  1  6  0  0  0
M  CHG  1  23  -1
M  END
> <DATABASE_ID>
MMDBc0054936

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](CO)(CCOC(C)=O)C1=C(O)C=C2C(=O)C3=C(C(O)=CC([O-])=C3)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O9/c1-8(22)29-3-2-9(7-21)15-14(25)6-12-17(19(15)27)20(28)16-11(18(12)26)4-10(23)5-13(16)24/h4-6,9,21,23-25,27H,2-3,7H2,1H3/p-1/t9-/m1/s1

> <INCHI_KEY>
BWYUKBCRHDFWFF-SECBINFHSA-M

> <FORMULA>
C20H17O9

> <MOLECULAR_WEIGHT>
401.348

> <EXACT_MASS>
401.087805707

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.52319796012459

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2S)-4-(acetyloxy)-1-hydroxybutan-2-yl]-4,5,7-trihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-olate

> <JCHEM_LOGP>
2.339744510666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.537255550013608

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.917811687426222

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7049277981639843

> <JCHEM_POLAR_SURFACE_AREA>
164.42

> <JCHEM_REFRACTIVITY>
111.34859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2S)-4-(acetyloxy)-1-hydroxybutan-2-yl]-4,5,7-trihydroxy-9,10-dioxoanthracen-2-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       7.026   2.516   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.646   5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.876   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.266  13.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.956  14.519   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.266   7.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.956   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.566   2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.186   5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.496  14.519   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.496  11.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.496   9.185   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.186  13.186   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.496   6.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.956   6.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.956  11.852   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.956   9.185   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.266  10.518   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.186   7.851   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.186  10.518   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.186   2.516   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   1.183   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.266  15.853   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0      11.646  13.186   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.266   5.184   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      17.806  10.518   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.646   7.851   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      11.646  10.518   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      12.416   3.850   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    3    9                                                       
CONECT    3    2   29                                                       
CONECT    4   10   11                                                       
CONECT    5   10   13                                                       
CONECT    6   12   14                                                       
CONECT    7    9   21                                                       
CONECT    8    1   22   29                                                  
CONECT    9    2    7   15   30                                             
CONECT   10    4    5   23                                                  
CONECT   11    4   16   18                                                  
CONECT   12    6   17   18                                                  
CONECT   13    5   16   24                                                  
CONECT   14    6   15   25                                                  
CONECT   15    9   14   19                                                  
CONECT   16   11   13   20                                                  
CONECT   17   12   19   20                                                  
CONECT   18   11   12   26                                                  
CONECT   19   15   17   27                                                  
CONECT   20   16   17   28                                                  
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23   10                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29    3    8                                                       
CONECT   30    9                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Synonyms

Value	Source
(3S)-Versiconol acetate	ChEBI
(3S)-Versiconol acetic acid	Generator
(3S)-Versiconol acetic acid(1-)	Generator

Molecular Formula

C₂₀H₁₇O₉

Average Mass

401.348

Monoisotopic Mass

401.087805707

IUPAC Name

6-[(2S)-4-(acetyloxy)-1-hydroxybutan-2-yl]-4,5,7-trihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-olate

Traditional Name

6-[(2S)-4-(acetyloxy)-1-hydroxybutan-2-yl]-4,5,7-trihydroxy-9,10-dioxoanthracen-2-olate

CAS Registry Number

Not Available

SMILES

[H][C@](CO)(CCOC(C)=O)C1=C(O)C=C2C(=O)C3=C(C(O)=CC([O-])=C3)C(=O)C2=C1O

InChI Identifier

InChI=1S/C20H18O9/c1-8(22)29-3-2-9(7-21)15-14(25)6-12-17(19(15)27)20(28)16-11(18(12)26)4-10(23)5-13(16)24/h4-6,9,21,23-25,27H,2-3,7H2,1H3/p-1/t9-/m1/s1

InChI Key

BWYUKBCRHDFWFF-SECBINFHSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenoxide
Vinylogous acid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary alcohol
Organic anion
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

versiconol acetate(1-) (CHEBI:72673 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.34	ChemAxon
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	164.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.35 m³·mol⁻¹	ChemAxon
Polarizability	38.52 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	Yes	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	4

Exposure Sources

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

28639093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71296167

PDB ID

Not Available

ChEBI ID

72673

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (3S)-versiconol acetic acid (MMDBc0054936)

MOL for #<Metabolite:0x00007fdaf57a0df0>

3D MOL for #<Metabolite:0x00007fdaf57a0df0>

3D SDF for #<Metabolite:0x00007fdaf57a0df0>

3D-SDF for #<Metabolite:0x00007fdaf57a0df0>

PDB for #<Metabolite:0x00007fdaf57a0df0>

3D PDB for #<Metabolite:0x00007fdaf57a0df0>

SMILES for #<Metabolite:0x00007fdaf57a0df0>

INCHI for #<Metabolite:0x00007fdaf57a0df0>

Structure for #<Metabolite:0x00007fdaf57a0df0>

3D Structure for #<Metabolite:0x00007fdaf57a0df0>