MiMeDB: Showing metabocard for Anthracyclinone blue B (MMDBc0010573)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:42:18 UTC

Update Date

2022-08-31 06:31:55 UTC

Metabolite ID

MMDBc0010573

Metabolite Identification

Common Name

Anthracyclinone blue B

Description

Anthracyclinone Blue B belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. Based on a literature review very few articles have been published on Anthracyclinone Blue B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104422D          

 33 36  0  0  0  0            999 V2000
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    4.2868    2.4750    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
    3.5724    2.0625    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
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    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
    3.5724    4.5375    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 11  1  0  0  0  0
 20 18  1  0  0  0  0
 21 15  1  0  0  0  0
 21 19  1  0  0  0  0
 22 16  1  0  0  0  0
 22 19  2  0  0  0  0
 23 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24 14  1  0  0  0  0
 25  7  1  0  0  0  0
 25 12  1  0  0  0  0
 26  8  1  0  0  0  0
 27 13  1  0  0  0  0
 28 20  2  0  0  0  0
 29 21  2  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 32 24  2  0  0  0  0
 33  2  1  0  0  0  0
 33 24  1  0  0  0  0
M  END


  Mrv1652305152104422D          

 33 36  0  0  0  0            999 V2000
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    4.2868    2.4750    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
    3.5724    2.0625    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
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    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
    3.5724    4.5375    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 11  1  0  0  0  0
 20 18  1  0  0  0  0
 21 15  1  0  0  0  0
 21 19  1  0  0  0  0
 22 16  1  0  0  0  0
 22 19  2  0  0  0  0
 23 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24 14  1  0  0  0  0
 25  7  1  0  0  0  0
 25 12  1  0  0  0  0
 26  8  1  0  0  0  0
 27 13  1  0  0  0  0
 28 20  2  0  0  0  0
 29 21  2  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 32 24  2  0  0  0  0
 33  2  1  0  0  0  0
 33 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0010573

> <DATABASE_NAME>
MIME

> <SMILES>
CCC1=CC(NCCO)=C2C(O)=C3C(=O)C4=C(C=CC=C4O)C(=O)C3=C(O)C2=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H21NO8/c1-3-10-9-12(25-7-8-26)16-17(14(10)24(32)33-2)23(31)18-19(22(16)30)21(29)15-11(20(18)28)5-4-6-13(15)27/h4-6,9,25-27,30-31H,3,7-8H2,1-2H3

> <INCHI_KEY>
QZOYVKFIBGXGPC-UHFFFAOYSA-N

> <FORMULA>
C24H21NO8

> <MOLECULAR_WEIGHT>
451.431

> <EXACT_MASS>
451.12671664

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
46.63294689964682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-ethyl-5,7,12-trihydroxy-4-[(2-hydroxyethyl)amino]-6,11-dioxo-6,11-dihydrotetracene-1-carboxylate

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
4.69163

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.323327309448871

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.614104781353737

> <JCHEM_PKA_STRONGEST_BASIC>
1.5720286630827536

> <JCHEM_POLAR_SURFACE_AREA>
153.39

> <JCHEM_REFRACTIVITY>
121.69749999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-ethyl-5,7,12-trihydroxy-4-[(2-hydroxyethyl)amino]-6,11-dioxotetracene-1-carboxylate

> <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      14.670   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      12.003   2.310   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      14.670  -0.770   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       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.337   9.240   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   33                                                            
CONECT    3    1   10                                                       
CONECT    4    5    6                                                       
CONECT    5    4   11                                                       
CONECT    6    4   13                                                       
CONECT    7    8   25                                                       
CONECT    8    7   26                                                       
CONECT    9   10   12                                                       
CONECT   10    3    9   14                                                  
CONECT   11    5   15   20                                                  
CONECT   12    9   16   25                                                  
CONECT   13    6   15   27                                                  
CONECT   14   10   17   24                                                  
CONECT   15   11   13   21                                                  
CONECT   16   12   17   22                                                  
CONECT   17   14   16   23                                                  
CONECT   18   19   20   23                                                  
CONECT   19   18   21   22                                                  
CONECT   20   11   18   28                                                  
CONECT   21   15   19   29                                                  
CONECT   22   16   19   30                                                  
CONECT   23   17   18   31                                                  
CONECT   24   14   32   33                                                  
CONECT   25    7   12                                                       
CONECT   26    8                                                            
CONECT   27   13                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33    2   24                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₂₁NO₈

Average Mass

451.431

Monoisotopic Mass

451.12671664

IUPAC Name

methyl 2-ethyl-5,7,12-trihydroxy-4-[(2-hydroxyethyl)amino]-6,11-dioxo-6,11-dihydrotetracene-1-carboxylate

Traditional Name

methyl 2-ethyl-5,7,12-trihydroxy-4-[(2-hydroxyethyl)amino]-6,11-dioxotetracene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CCC1=CC(NCCO)=C2C(O)=C3C(=O)C4=C(C=CC=C4O)C(=O)C3=C(O)C2=C1C(=O)OC

InChI Identifier

InChI=1S/C24H21NO8/c1-3-10-9-12(25-7-8-26)16-17(14(10)24(32)33-2)23(31)18-19(22(16)30)21(29)15-11(20(18)28)5-4-6-13(15)27/h4-6,9,25-27,30-31H,3,7-8H2,1-2H3

InChI Key

QZOYVKFIBGXGPC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
9,10-anthraquinone
1,4-anthraquinone
1-naphthalenecarboxylic acid or derivatives
1-naphthol
Aminobenzoic acid or derivatives
Aryl ketone
Hydroquinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Phenol
Vinylogous acid
Methyl ester
Amino acid or derivatives
1,2-aminoalcohol
Carboxylic acid ester
Ketone
Alkanolamine
Carboxylic acid derivative
Polyol
Secondary amine
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Amine
Primary alcohol
Organonitrogen compound
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
Water Solubility	0.028 g/L	ALOGPS
logP	3.77	ALOGPS
logP	4.69	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	1.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.39 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.7 m³·mol⁻¹	ChemAxon
Polarizability	46.63 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	Yes	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

Not Available

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
Bacteria	Actinobacteria	1		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

17624913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16720549

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Anthracyclinone blue B (MMDBc0010573)

MOL for #<Metabolite:0x00007fecec013520>

3D MOL for #<Metabolite:0x00007fecec013520>

3D SDF for #<Metabolite:0x00007fecec013520>

3D-SDF for #<Metabolite:0x00007fecec013520>

PDB for #<Metabolite:0x00007fecec013520>

3D PDB for #<Metabolite:0x00007fecec013520>

SMILES for #<Metabolite:0x00007fecec013520>

INCHI for #<Metabolite:0x00007fecec013520>

Structure for #<Metabolite:0x00007fecec013520>

3D Structure for #<Metabolite:0x00007fecec013520>