MiMeDB: Showing metabocard for (2S-3S)-versiconal hemiacetal (MMDBc0054838)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:36:00 UTC

Update Date

2022-08-12 20:09:06 UTC

MiMeDB ID

MMDBc0054838

Metabolite Identification

Common Name

(2S-3S)-versiconal hemiacetal

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221362D          

 28 31  0  0  1  0            999 V2000
    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
    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
    0.5363    5.1687    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
    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
  2  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  1  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 19  2  1  0  0  0  0
 20  6  1  0  0  0  0
 21 10  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  2  0  0  0  0
 24 17  1  0  0  0  0
 18 25  1  6  0  0  0
 26 11  1  0  0  0  0
 26 18  1  0  0  0  0
  7 27  1  6  0  0  0
 18 28  1  1  0  0  0
M  CHG  1  20  -1
M  END


  Mrv1652306172221362D          

 28 31  0  0  1  0            999 V2000
    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
    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
    0.5363    5.1687    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
    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
  2  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  1  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 19  2  1  0  0  0  0
 20  6  1  0  0  0  0
 21 10  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  2  0  0  0  0
 24 17  1  0  0  0  0
 18 25  1  6  0  0  0
 26 11  1  0  0  0  0
 26 18  1  0  0  0  0
  7 27  1  6  0  0  0
 18 28  1  1  0  0  0
M  CHG  1  20  -1
M  END
> <DATABASE_ID>
MMDBc0054838

> <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])CCO

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O8/c19-2-1-7-13-11(26-18(7)25)5-9-14(17(13)24)16(23)12-8(15(9)22)3-6(20)4-10(12)21/h3-5,7,18-21,24-25H,1-2H2/p-1/t7-,18-/m0/s1

> <INCHI_KEY>
CMMJVRKBQZHKPV-VIIUKITBSA-M

> <FORMULA>
C18H13O8

> <MOLECULAR_WEIGHT>
357.295

> <EXACT_MASS>
357.061590959

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.577084316013796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.084515550333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.343278063671853

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.292985582851966

> <JCHEM_PKA_STRONGEST_BASIC>
-2.385552616953447

> <JCHEM_POLAR_SURFACE_AREA>
147.35

> <JCHEM_REFRACTIVITY>
99.50319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2,4,6-trihydroxy-3-(2-hydroxyethyl)-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       2.983   7.863   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.477   8.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.459   6.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.554   5.153   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.001   9.648   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.260   3.613   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0      11.592   8.233   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.925   2.073   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.925   8.233   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.014   5.153   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.459   3.907   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       4.548   7.488   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.855   3.781   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1   19                                                       
CONECT    3    6    8                                                       
CONECT    4    6   10                                                       
CONECT    5    9   11                                                       
CONECT    6    3    4   20                                                  
CONECT    7    1   13   18   27                                             
CONECT    8    3   12   15                                                  
CONECT    9    5   14   15                                                  
CONECT   10    4   12   21                                                  
CONECT   11    5   13   26                                                  
CONECT   12    8   10   16                                                  
CONECT   13    7   11   17                                                  
CONECT   14    9   16   17                                                  
CONECT   15    8    9   22                                                  
CONECT   16   12   14   23                                                  
CONECT   17   13   14   24                                                  
CONECT   18    7   25   26   28                                             
CONECT   19    2                                                            
CONECT   20    6                                                            
CONECT   21   10                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   11   18                                                       
CONECT   27    7                                                            
CONECT   28   18                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

Synonyms

Value	Source
(2S-3S)-Versiconal hemiacetal	ChEBI

Chemical Formula

C₁₈H₁₃O₈

Average Molecular Weight

357.295

Monoisotopic Molecular Weight

357.061590959

IUPAC Name

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

Traditional Name

(2S,3S)-2,4,6-trihydroxy-3-(2-hydroxyethyl)-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])CCO

InChI Identifier

InChI=1S/C18H14O8/c19-2-1-7-13-11(26-18(7)25)5-9-14(17(13)24)16(23)12-8(15(9)22)3-6(20)4-10(12)21/h3-5,7,18-21,24-25H,1-2H2/p-1/t7-,18-/m0/s1

InChI Key

CMMJVRKBQZHKPV-VIIUKITBSA-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
Naphthofuran
Coumaran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenoxide
Vinylogous acid
Hemiacetal
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenolate anion (CHEBI:77950 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.08	ChemAxon
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	147.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.5 m³·mol⁻¹	ChemAxon
Polarizability	34.58 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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	5

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

31150444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86289428

PDB ID

Not Available

ChEBI ID

77950

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 (2S-3S)-versiconal hemiacetal (MMDBc0054838)

MOL for #<Metabolite:0x000055b76dd12d90>

3D MOL for #<Metabolite:0x000055b76dd12d90>

3D SDF for #<Metabolite:0x000055b76dd12d90>

3D-SDF for #<Metabolite:0x000055b76dd12d90>

PDB for #<Metabolite:0x000055b76dd12d90>

3D PDB for #<Metabolite:0x000055b76dd12d90>

SMILES for #<Metabolite:0x000055b76dd12d90>

INCHI for #<Metabolite:0x000055b76dd12d90>

Structure for #<Metabolite:0x000055b76dd12d90>

3D Structure for #<Metabolite:0x000055b76dd12d90>