MiMeDB: Showing metabocard for 2-acetyl-3,4a,8,10,11,12a-hexahydroxy-1,4,4a,5,12,12a-hexahydrotetracene-1,12-dione (MMDBc0055205)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:46:12 UTC

Update Date

2022-08-12 20:09:16 UTC

Metabolite ID

MMDBc0055205

Metabolite Identification

Common Name

2-acetyl-3,4a,8,10,11,12a-hexahydroxy-1,4,4a,5,12,12a-hexahydrotetracene-1,12-dione

Description

8-acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-6,6a,7,10,10a,11-hexahydrotetracen-2-olate belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Based on a literature review very few articles have been published on 8-acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-6,6a,7,10,10a,11-hexahydrotetracen-2-olate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221462D          

 29 32  0  0  0  0            999 V2000
   -0.7145   -1.2375    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  5  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
  9  5  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  4  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21  7  2  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  2  0  0  0  0
 27 18  2  0  0  0  0
 28 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  CHG  1  22  -1
M  END


  Mrv1652306172221462D          

 29 32  0  0  0  0            999 V2000
   -0.7145   -1.2375    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  5  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
  9  5  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  4  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21  7  2  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  2  0  0  0  0
 27 18  2  0  0  0  0
 28 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  CHG  1  22  -1
M  END
> <DATABASE_ID>
MMDBc0055205

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)C1=C(O)CC2(O)CC3=C(C(O)=C4C(O)=CC([O-])=CC4=C3)C(=O)C2(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O9/c1-7(21)13-12(24)6-19(28)5-9-2-8-3-10(22)4-11(23)14(8)16(25)15(9)18(27)20(19,29)17(13)26/h2-4,22-25,28-29H,5-6H2,1H3/p-1

> <INCHI_KEY>
QUQTYIYOYNVOJS-UHFFFAOYSA-M

> <FORMULA>
C20H15O9

> <MOLECULAR_WEIGHT>
399.332

> <EXACT_MASS>
399.072155643

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.29456787028258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-6,6a,7,10,10a,11-hexahydrotetracen-2-olate

> <JCHEM_LOGP>
0.8623652083333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.719592081214134

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4556880793895894

> <JCHEM_PKA_STRONGEST_BASIC>
-3.688197488922957

> <JCHEM_POLAR_SURFACE_AREA>
175.42

> <JCHEM_REFRACTIVITY>
109.98149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-10,11-dihydrotetracen-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      -1.334  -2.310   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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8    9                                                       
CONECT    3    8   10                                                       
CONECT    4   10   11                                                       
CONECT    5    9   19                                                       
CONECT    6   12   19                                                       
CONECT    7    1   13   21                                                  
CONECT    8    2    3   14                                                  
CONECT    9    2    5   15                                                  
CONECT   10    3    4   22                                                  
CONECT   11    4   14   23                                                  
CONECT   12    6   13   24                                                  
CONECT   13    7   12   17                                                  
CONECT   14    8   11   16                                                  
CONECT   15    9   16   18                                                  
CONECT   16   14   15   25                                                  
CONECT   17   13   20   26                                                  
CONECT   18   15   20   27                                                  
CONECT   19    5    6   20   28                                             
CONECT   20   17   18   19   29                                             
CONECT   21    7                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

Synonyms

Value	Source
8-Acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-6,6a,7,10,10a,11-hexahydrotetracen-2-olic acid	Generator

Molecular Formula

C₂₀H₁₅O₉

Average Mass

399.332

Monoisotopic Mass

399.072155643

IUPAC Name

8-acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-6,6a,7,10,10a,11-hexahydrotetracen-2-olate

Traditional Name

8-acetyl-4,5,6a,9,10a-pentahydroxy-6,7-dioxo-10,11-dihydrotetracen-2-olate

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)CC2(O)CC3=C(C(O)=C4C(O)=CC([O-])=CC4=C3)C(=O)C2(O)C1=O

InChI Identifier

InChI=1S/C20H16O9/c1-7(21)13-12(24)6-19(28)5-9-2-8-3-10(22)4-11(23)14(8)16(25)15(9)18(27)20(19,29)17(13)26/h2-4,22-25,28-29H,5-6H2,1H3/p-1

InChI Key

QUQTYIYOYNVOJS-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
2-naphthol
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Vinylogous acid
Tertiary alcohol
Ketone
1,2-diol
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic anion
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.86	ChemAxon
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	175.42 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	109.98 m³·mol⁻¹	ChemAxon
Polarizability	37.29 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

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	2	Human feces

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 2-acetyl-3,4a,8,10,11,12a-hexahydroxy-1,4,4a,5,12,12a-hexahydrotetracene-1,12-dione (MMDBc0055205)

MOL for #<Metabolite:0x00007fdb0818dce8>

3D MOL for #<Metabolite:0x00007fdb0818dce8>

3D SDF for #<Metabolite:0x00007fdb0818dce8>

3D-SDF for #<Metabolite:0x00007fdb0818dce8>

PDB for #<Metabolite:0x00007fdb0818dce8>

3D PDB for #<Metabolite:0x00007fdb0818dce8>

SMILES for #<Metabolite:0x00007fdb0818dce8>

INCHI for #<Metabolite:0x00007fdb0818dce8>

Structure for #<Metabolite:0x00007fdb0818dce8>

3D Structure for #<Metabolite:0x00007fdb0818dce8>