MiMeDB: Showing metabocard for (2S,3S)-versiconal hemiacetal acetic acid (MMDBc0054844)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:36:10 UTC

Update Date

2022-08-12 20:09:06 UTC

Metabolite ID

MMDBc0054844

Metabolite Identification

Common Name

(2S,3S)-versiconal hemiacetal acetic acid

Description

(2S,3S)-versiconal hemiacetal acetate(1-) 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 (2S,3S)-versiconal hemiacetal acetate(1-).

Structure

MOL SDF PDB SMILES InChI

  Mrv1652306172221362D          

 31 34  0  0  1  0            999 V2000
   -0.5256    6.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983    4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913    4.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706    5.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    3.4279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8227    4.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433    2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    5.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    4.0112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    2.0254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  1  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20  9  1  0  0  0  0
 21  7  2  0  0  0  0
 22  8  1  0  0  0  0
 23 12  1  0  0  0  0
 24 17  2  0  0  0  0
 25 18  2  0  0  0  0
 26 19  1  0  0  0  0
 20 27  1  6  0  0  0
 28  3  1  0  0  0  0
 28  7  1  0  0  0  0
 29 13  1  0  0  0  0
 29 20  1  0  0  0  0
  9 30  1  6  0  0  0
 20 31  1  1  0  0  0
M  CHG  1  22  -1
M  END

  Mrv1652306172221362D          

 31 34  0  0  1  0            999 V2000
   -0.5256    6.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983    4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913    4.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706    5.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    3.4279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8227    4.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433    2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    5.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    4.0112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    2.0254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  1  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20  9  1  0  0  0  0
 21  7  2  0  0  0  0
 22  8  1  0  0  0  0
 23 12  1  0  0  0  0
 24 17  2  0  0  0  0
 25 18  2  0  0  0  0
 26 19  1  0  0  0  0
 20 27  1  6  0  0  0
 28  3  1  0  0  0  0
 28  7  1  0  0  0  0
 29 13  1  0  0  0  0
 29 20  1  0  0  0  0
  9 30  1  6  0  0  0
 20 31  1  1  0  0  0
M  CHG  1  22  -1
M  END
> <DATABASE_ID>
MMDBc0054844

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O)OC2=C(C(O)=C3C(=O)C4=C(C=C([O-])C=C4O)C(=O)C3=C2)[C@]1([H])CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O9/c1-7(21)28-3-2-9-15-13(29-20(9)27)6-11-16(19(15)26)18(25)14-10(17(11)24)4-8(22)5-12(14)23/h4-6,9,20,22-23,26-27H,2-3H2,1H3/p-1/t9-,20-/m0/s1

> <INCHI_KEY>
DYJNRRXQVSJBAA-LXGOIASLSA-M

> <FORMULA>
C20H15O9

> <MOLECULAR_WEIGHT>
399.332

> <EXACT_MASS>
399.072155643

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.949263537684665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-3-[2-(acetyloxy)ethyl]-2,4,6-trihydroxy-5,10-dioxo-2H,3H,5H,10H-anthra[2,3-b]furan-8-olate

> <JCHEM_LOGP>
2.5256409606666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.966752421401425

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.213182986419784

> <JCHEM_PKA_STRONGEST_BASIC>
-4.241333261547408

> <JCHEM_POLAR_SURFACE_AREA>
153.42

> <JCHEM_REFRACTIVITY>
108.65469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-[2-(acetyloxy)ethyl]-2,4,6-trihydroxy-5,10-dioxo-2H,3H-anthra[2,3-b]furan-8-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      -0.981  11.433   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.983   7.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.477   8.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.505   9.968   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.459   6.399   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.554   5.153   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.536   8.824   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.260   3.613   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      11.592   8.233   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.925   2.073   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.925   8.233   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.014   5.153   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.001   9.648   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.459   3.907   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.548   7.488   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.855   3.781   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    3    9                                                       
CONECT    3    2   28                                                       
CONECT    4    8   10                                                       
CONECT    5    8   12                                                       
CONECT    6   11   13                                                       
CONECT    7    1   21   28                                                  
CONECT    8    4    5   22                                                  
CONECT    9    2   15   20   30                                             
CONECT   10    4   14   17                                                  
CONECT   11    6   16   17                                                  
CONECT   12    5   14   23                                                  
CONECT   13    6   15   29                                                  
CONECT   14   10   12   18                                                  
CONECT   15    9   13   19                                                  
CONECT   16   11   18   19                                                  
CONECT   17   10   11   24                                                  
CONECT   18   14   16   25                                                  
CONECT   19   15   16   26                                                  
CONECT   20    9   27   29   31                                             
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23   12                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28    3    7                                                       
CONECT   29   13   20                                                       
CONECT   30    9                                                            
CONECT   31   20                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Synonyms

Value	Source
(2S,3S)-Versiconal hemiacetal acetate	ChEBI
(2S,3S)-Versiconal hemiacetal acetic acid	Generator
(2S,3S)-Versiconal hemiacetal acetic acid(1-)	Generator

Molecular Formula

C₂₀H₁₅O₉

Average Mass

399.332

Monoisotopic Mass

399.072155643

IUPAC Name

(2S,3S)-3-[2-(acetyloxy)ethyl]-2,4,6-trihydroxy-5,10-dioxo-2H,3H,5H,10H-anthra[2,3-b]furan-8-olate

Traditional Name

(2S,3S)-3-[2-(acetyloxy)ethyl]-2,4,6-trihydroxy-5,10-dioxo-2H,3H-anthra[2,3-b]furan-8-olate

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)OC2=C(C(O)=C3C(=O)C4=C(C=C([O-])C=C4O)C(=O)C3=C2)[C@]1([H])CCOC(C)=O

InChI Identifier

InChI=1S/C20H16O9/c1-7(21)28-3-2-9-15-13(29-20(9)27)6-11-16(19(15)26)18(25)14-10(17(11)24)4-8(22)5-12(14)23/h4-6,9,20,22-23,26-27H,2-3H2,1H3/p-1/t9-,20-/m0/s1

InChI Key

DYJNRRXQVSJBAA-LXGOIASLSA-M

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for (2S,3S)-versiconal hemiacetal acetic acid (MMDBc0054844)

MOL for #<Metabolite:0x00007fd5d0d85bf0>

3D MOL for #<Metabolite:0x00007fd5d0d85bf0>

3D SDF for #<Metabolite:0x00007fd5d0d85bf0>

3D-SDF for #<Metabolite:0x00007fd5d0d85bf0>

PDB for #<Metabolite:0x00007fd5d0d85bf0>

3D PDB for #<Metabolite:0x00007fd5d0d85bf0>

SMILES for #<Metabolite:0x00007fd5d0d85bf0>

INCHI for #<Metabolite:0x00007fd5d0d85bf0>

Structure for #<Metabolite:0x00007fd5d0d85bf0>

3D Structure for #<Metabolite:0x00007fd5d0d85bf0>