MiMeDB: Showing metabocard for Versiconol (MMDBc0015885)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:38:59 UTC

Update Date

2022-08-31 06:39:56 UTC

Metabolite ID

MMDBc0015885

Metabolite Identification

Common Name

Versiconol

Description

(S)-versiconol 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 (S)-versiconol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108392D          

 27 29  0  0  1  0            999 V2000
    3.5724    2.0625    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
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  1  1  1  0  0  0
  7  6  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  2  1  0  0  0  0
 20  6  1  0  0  0  0
 21  8  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24 16  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  2  0  0  0  0
  7 27  1  6  0  0  0
M  END


  Mrv1652305152108392D          

 27 29  0  0  1  0            999 V2000
    3.5724    2.0625    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
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  1  1  1  0  0  0
  7  6  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  2  1  0  0  0  0
 20  6  1  0  0  0  0
 21  8  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24 16  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  2  0  0  0  0
  7 27  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015885

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O8/c19-2-1-7(6-20)13-12(23)5-10-15(17(13)25)18(26)14-9(16(10)24)3-8(21)4-11(14)22/h3-5,7,19-23,25H,1-2,6H2/t7-/m1/s1

> <INCHI_KEY>
ZLIRCPWCWHTYNP-SSDOTTSWSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.318

> <EXACT_MASS>
360.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.053166333147686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S)-1,4-dihydroxybutan-2-yl]-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
1.8986191003333335

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.883579598275262

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.194686789744955

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3833350406832823

> <JCHEM_POLAR_SURFACE_AREA>
155.51999999999998

> <JCHEM_REFRACTIVITY>
91.64679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S)-1,4-dihydroxybutan-2-yl]-1,3,6,8-tetrahydroxyanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  15.400   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       8.002   3.080   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1   19                                                       
CONECT    3    8    9                                                       
CONECT    4    8   11                                                       
CONECT    5   10   12                                                       
CONECT    6    7   20                                                       
CONECT    7    1    6   13   27                                             
CONECT    8    3    4   21                                                  
CONECT    9    3   14   16                                                  
CONECT   10    5   15   16                                                  
CONECT   11    4   14   22                                                  
CONECT   12    5   13   23                                                  
CONECT   13    7   12   17                                                  
CONECT   14    9   11   18                                                  
CONECT   15   10   17   18                                                  
CONECT   16    9   10   24                                                  
CONECT   17   13   15   25                                                  
CONECT   18   14   15   26                                                  
CONECT   19    2                                                            
CONECT   20    6                                                            
CONECT   21    8                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   18                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Synonyms

Value	Source
Versiconol	MeSH

Molecular Formula

C₁₈H₁₆O₈

Average Mass

360.318

Monoisotopic Mass

360.084517475

IUPAC Name

2-[(2S)-1,4-dihydroxybutan-2-yl]-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-[(2S)-1,4-dihydroxybutan-2-yl]-1,3,6,8-tetrahydroxyanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H16O8/c19-2-1-7(6-20)13-12(23)5-10-15(17(13)25)18(26)14-9(16(10)24)3-8(21)4-11(14)22/h3-5,7,19-23,25H,1-2,6H2/t7-/m1/s1

InChI Key

ZLIRCPWCWHTYNP-SSDOTTSWSA-N

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
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

versiconol (CHEBI:71665 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	1.16	ALOGPS
logP	1.9	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.19	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.65 m³·mol⁻¹	ChemAxon
Polarizability	35.05 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015430	Versiconol	(2S-3S)-versiconal hemiacetal	Versiconal hemiacetal acetate reductase	Reduction	RHEA	34755880
MMDBr0015433	(3S)-versiconol acetic acid	Versiconol	Versiconal hemiacetal acetate esterase	Ester hydrolysis	RHEA	34755880

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

Source Type	Source Sub-type	Species	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

141760

KEGG Compound ID

C20508

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161385

PDB ID

Not Available

ChEBI ID

71665

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 Versiconol (MMDBc0015885)

MOL for #<Metabolite:0x00007fa4ac08dc40>

3D MOL for #<Metabolite:0x00007fa4ac08dc40>

3D SDF for #<Metabolite:0x00007fa4ac08dc40>

3D-SDF for #<Metabolite:0x00007fa4ac08dc40>

PDB for #<Metabolite:0x00007fa4ac08dc40>

3D PDB for #<Metabolite:0x00007fa4ac08dc40>

SMILES for #<Metabolite:0x00007fa4ac08dc40>

INCHI for #<Metabolite:0x00007fa4ac08dc40>

Structure for #<Metabolite:0x00007fa4ac08dc40>

3D Structure for #<Metabolite:0x00007fa4ac08dc40>