NP-MRD: Showing NP-Card for Chrysoobtusin (NP0047903)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:50 UTC

Updated at

2022-03-17 20:47:50 UTC

NP-MRD ID

NP0047903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chrysoobtusin

Description

Chrysoobtusin 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. Chrysoobtusin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chrysoobtusin has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and pulses. Chrysoobtusin is found in Cassia tora , Senna obtusifolia and Senna tora. This could make chrysoobtusin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307392D          

 26 28  0  0  0  0            999 V2000
    5.7158    0.8250    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    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
    0.7145    3.7125    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
    1.4289    0.8250    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
    3.5724    1.2375    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
    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
    5.0013    2.0625    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
    2.8579    2.4750    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
    4.2868    2.4750    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
    5.7158    2.4750    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
    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
    0.0000    2.4750    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  2  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 18  1  0  0  0  0
 26  5  1  0  0  0  0
 26 19  1  0  0  0  0
M  END


  Mrv0541 05061307392D          

 26 28  0  0  0  0            999 V2000
    5.7158    0.8250    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    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
    0.7145    3.7125    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
    1.4289    0.8250    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
    3.5724    1.2375    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
    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
    5.0013    2.0625    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
    2.8579    2.4750    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
    4.2868    2.4750    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
    5.7158    2.4750    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
    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
    0.0000    2.4750    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  2  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 18  1  0  0  0  0
 26  5  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-8-6-9-12(18(25-4)14(8)20)16(22)13-10(15(9)21)7-11(23-2)17(24-3)19(13)26-5/h6-7,20H,1-5H3

> <INCHI_KEY>
ZMDXTRSTKHTSCE-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.342

> <EXACT_MASS>
358.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60717922087847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1,6,7,8-tetramethoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.497877079666666

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.290916806815265

> <JCHEM_PKA_STRONGEST_BASIC>
-4.352133169477481

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
94.0259

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1,6,7,8-tetramethoxy-3-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   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   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  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   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
HETATM   24  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    8    9                                                       
CONECT    7   10   11                                                       
CONECT    8    1    6   14                                                  
CONECT    9    6   12   15                                                  
CONECT   10    7   13   15                                                  
CONECT   11    7   17   23                                                  
CONECT   12    9   16   18                                                  
CONECT   13   10   16   19                                                  
CONECT   14    8   18   20                                                  
CONECT   15    9   10   21                                                  
CONECT   16   12   13   22                                                  
CONECT   17   11   19   24                                                  
CONECT   18   12   14   25                                                  
CONECT   19   13   17   26                                                  
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    2   11                                                       
CONECT   24    3   17                                                       
CONECT   25    4   18                                                       
CONECT   26    5   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-1,6,7,8-tetramethoxy-3-methylanthraquinone	HMDB

Chemical Formula

C₁₉H₁₈O₇

Average Mass

358.3420 Da

Monoisotopic Mass

358.10525 Da

IUPAC Name

2-hydroxy-1,6,7,8-tetramethoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-hydroxy-1,6,7,8-tetramethoxy-3-methylanthracene-9,10-dione

CAS Registry Number

70588-06-6

SMILES

COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1

InChI Identifier

InChI=1S/C19H18O7/c1-8-6-9-12(18(25-4)14(8)20)16(22)13-10(15(9)21)7-11(23-2)17(24-3)19(13)26-5/h6-7,20H,1-5H3

InChI Key

ZMDXTRSTKHTSCE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cassia tora	Plant	KNApSAcK
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Senna obtusifolia	LOTUS Database	35616633
Senna tora	LOTUS Database	35616633

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
Alkyl aryl ether
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:81263 )
Anthraquinone type (C17669 )

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	2.34	ALOGPS
logP	2.5	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.03 m³·mol⁻¹	ChemAxon
Polarizability	36.61 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

HMDB0034218

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012522

KNApSAcK ID

Not Available

Chemspider ID

136879

KEGG Compound ID

C17669

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chrysoobtusin (NP0047903)

MOL for NP0047903 (Chrysoobtusin)

3D MOL for NP0047903 (Chrysoobtusin)

3D SDF for NP0047903 (Chrysoobtusin)

3D-SDF for NP0047903 (Chrysoobtusin)

PDB for NP0047903 (Chrysoobtusin)

3D PDB for NP0047903 (Chrysoobtusin)

SMILES for NP0047903 (Chrysoobtusin)

INCHI for NP0047903 (Chrysoobtusin)

Structure for NP0047903 (Chrysoobtusin)

3D Structure for NP0047903 (Chrysoobtusin)