MiMeDB: Showing metabocard for Norsolorinic acid (MMDBc0016864)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:23:51 UTC

Update Date

2022-08-31 06:41:36 UTC

Metabolite ID

MMDBc0016864

Metabolite Identification

Common Name

Norsolorinic acid

Description

norsolorinic acid, also known as norsolorinate, 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. norsolorinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). A polyketide that is anthraquinone bearing four hydroxy substituents at positions 1, 3, 6 and 8 as well as a hexanoyl substituent at position 2.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241509062D          

 27 29  0  0  0  0            999 V2000
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv1533004241509062D          

 27 29  0  0  0  0            999 V2000
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016864

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC(=O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O7/c1-2-3-4-5-12(22)17-14(24)8-11-16(20(17)27)19(26)15-10(18(11)25)6-9(21)7-13(15)23/h6-8,21,23-24,27H,2-5H2,1H3

> <INCHI_KEY>
XIJDBHLQUYAZJI-UHFFFAOYSA-N

> <FORMULA>
C20H18O7

> <MOLECULAR_WEIGHT>
370.357

> <EXACT_MASS>
370.10525292

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
37.71734226849666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hexanoyl-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
5.896334148666667

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.332149821993286

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.718988979875418

> <JCHEM_PKA_STRONGEST_BASIC>
-4.594231685871482

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
97.90729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hexanoyl-1,3,6,8-tetrahydroxyanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004  -6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      17.338  -3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.672  -6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      21.339  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.339  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.673  -8.470   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.006  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      22.673 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.006 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      25.340 -13.090   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      22.673 -13.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      20.005 -13.090   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.339 -10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      18.672 -10.780   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      20.005  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.338  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   12   26                                                  
CONECT   26   25    8   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Synonyms

Value	Source
Norsolorinate	Kegg
2-Hexanoyl-1,3,6,8-tetrahydroxy-9,10-anthraquinone	Kegg

Molecular Formula

C₂₀H₁₈O₇

Average Mass

370.357

Monoisotopic Mass

370.10525292

IUPAC Name

2-hexanoyl-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-hexanoyl-1,3,6,8-tetrahydroxyanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C20H18O7/c1-2-3-4-5-12(22)17-14(24)8-11-16(20(17)27)19(26)15-10(18(11)25)6-9(21)7-13(15)23/h6-8,21,23-24,27H,2-5H2,1H3

InChI Key

XIJDBHLQUYAZJI-UHFFFAOYSA-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
Butyrophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:71356 )
polyketide (CHEBI:71356 )
hydroxyanthraquinones (CHEBI:71356 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.55	ALOGPS
logP	5.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.72	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.91 m³·mol⁻¹	ChemAxon
Polarizability	37.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	8	Human feces	Metabolic reconstruction

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

Not Available

KEGG Compound ID

C20452

BioCyc ID

CPD-10162

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71356

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 Norsolorinic acid (MMDBc0016864)

MOL for #<Metabolite:0x00007f667e9aa588>

3D MOL for #<Metabolite:0x00007f667e9aa588>

3D SDF for #<Metabolite:0x00007f667e9aa588>

3D-SDF for #<Metabolite:0x00007f667e9aa588>

PDB for #<Metabolite:0x00007f667e9aa588>

3D PDB for #<Metabolite:0x00007f667e9aa588>

SMILES for #<Metabolite:0x00007f667e9aa588>

INCHI for #<Metabolite:0x00007f667e9aa588>

Structure for #<Metabolite:0x00007f667e9aa588>

3D Structure for #<Metabolite:0x00007f667e9aa588>