NP-MRD: Showing NP-Card for 1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone (NP0334882)

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Record Information

Version

2.0

Created at

2024-09-10 22:54:58 UTC

Updated at

2024-09-10 22:54:58 UTC

NP-MRD ID

NP0334882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone

Description

1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone 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. 1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone has been detected, but not quantified in, fruits. This could make 1,3,5,8-tetrahydroxy-6-methoxy-2-methylanthraquinone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310562D          

 23 25  0  0  0  0            999 V2000
    5.7158    2.4750    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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
    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
    1.4289    2.4750    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
    3.5724    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
    2.1434    1.2375    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
    2.8579    0.8250    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23  2  1  0  0  0  0
 23  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(C(O)=C1)C(=O)C1=C(O)C(C)=C(O)C=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-5-7(17)3-6-10(13(5)19)16(22)11-8(18)4-9(23-2)15(21)12(11)14(6)20/h3-4,17-19,21H,1-2H3

> <INCHI_KEY>
WYAGLAMLQQEAEL-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.2623

> <EXACT_MASS>
316.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.36384354207567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,5,8-tetrahydroxy-6-methoxy-2-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
4.010194911666666

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.745491726285554

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.817196141949813

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5084586161442974

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
80.579

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,5,8-tetrahydroxy-6-methoxy-2-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   23                                                            
CONECT    3    6    7                                                       
CONECT    4    8    9                                                       
CONECT    5    1    7   13                                                  
CONECT    6    3   10   14                                                  
CONECT    7    3    5   17                                                  
CONECT    8    4   11   18                                                  
CONECT    9    4   15   23                                                  
CONECT   10    6   13   16                                                  
CONECT   11    8   12   16                                                  
CONECT   12   11   14   15                                                  
CONECT   13    5   10   19                                                  
CONECT   14    6   12   20                                                  
CONECT   15    9   12   21                                                  
CONECT   16   10   11   22                                                  
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2623 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

1,3,5,8-tetrahydroxy-6-methoxy-2-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,3,5,8-tetrahydroxy-6-methoxy-2-methylanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(C(O)=C1)C(=O)C1=C(O)C(C)=C(O)C=C1C2=O

InChI Identifier

InChI=1S/C16H12O7/c1-5-7(17)3-6-10(13(5)19)16(22)11-8(18)4-9(23-2)15(21)12(11)14(6)20/h3-4,17-19,21H,1-2H3

InChI Key

WYAGLAMLQQEAEL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.22	ALOGPS
logP	4.01	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.58 m³·mol⁻¹	ChemAxon
Polarizability	30.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039210

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018741

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

14285022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone (NP0334882)

MOL for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

3D MOL for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

3D SDF for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

3D-SDF for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

PDB for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

3D PDB for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

SMILES for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

INCHI for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

Structure for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)

3D Structure for NP0334882 (1,3,5,8-Tetrahydroxy-6-methoxy-2-methylanthraquinone)