NP-MRD: Showing NP-Card for 2-Hydroxyanthraquinone (NP0138398)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:45 UTC

Updated at

2022-05-31 17:57:45 UTC

NP-MRD ID

NP0138398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxyanthraquinone

Description

2-Hydroxyanthraquinone 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. In this case, the number n (which is between 1 and 8) is indicated by a multiplier prefix (mono-, di-, tri-, up to octa-). Additional hydroxy- compounds can be derived from the other isomers of the latter. 2-Hydroxyanthraquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). From 9,10-anthraquinone, only two single-hydroxy derivatives are possible. Usually "hydroxyanthraquinone" refers to a derivative of 9,10-anthraquinone. In general, the term may mean any anthraquinone derivative where any number n of hydrogens have been replaced by n hydroxyls, so that the formula is C14H10O2+n. A hydroxyanthraquinone (formula: C14H9O2(OH)) is any of several organic compounds that can be viewed as derivatives of an anthraquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH). 2-Hydroxyanthraquinone is found in Galium odoratum and Rubia tinctorum. The IUPAC nomenclature recommends hydroxyanthracenedione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304272018522D          

 17 19  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  2  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0138398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15H

> <INCHI_KEY>
GCDBEYOJCZLKMC-UHFFFAOYSA-N

> <FORMULA>
C14H8O3

> <MOLECULAR_WEIGHT>
224.215

> <EXACT_MASS>
224.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.505537177240313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.6151407530000004

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.298054919747748

> <JCHEM_PKA_STRONGEST_BASIC>
-6.967216153451607

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
63.13190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxyanthraquinone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.850   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.160   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.700   2.667   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.770   4.001   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.850  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   10                                                       
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7    8   12                                                       
CONECT    8    5    7   15                                                  
CONECT    9    3   10   13                                                  
CONECT   10    4    9   14                                                  
CONECT   11    6   12   13                                                  
CONECT   12    7   11   14                                                  
CONECT   13    9   11   16                                                  
CONECT   14   10   12   17                                                  
CONECT   15    8                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-9,10-anthracenedione	ChEBI
2-Hydroxy-9,10-anthraquinone	ChEBI
2-Hydroxyanthra-9,10-quinone	ChEBI
beta-Hydroxyanthraquinone	ChEBI
b-Hydroxyanthraquinone	Generator
Β-hydroxyanthraquinone	Generator

Chemical Formula

C₁₄H₈O₃

Average Mass

224.2150 Da

Monoisotopic Mass

224.04734 Da

IUPAC Name

2-hydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-hydroxyanthraquinone

CAS Registry Number

605-32-3

SMILES

OC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15H

InChI Key

GCDBEYOJCZLKMC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Asperula odorata	LOTUS Database	35616633
Rubia tinctorum	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
1-hydroxy-2-unsubstituted benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinone (CHEBI:37482 )

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	3.29	ALOGPS
logP	2.62	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.13 m³·mol⁻¹	ChemAxon
Polarizability	22.51 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Hydroxyanthraquinone

METLIN ID

Not Available

PubChem Compound

11796

PDB ID

Not Available

ChEBI ID

37482

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hydroxyanthraquinone (NP0138398)

MOL for NP0138398 (2-Hydroxyanthraquinone)

3D MOL for NP0138398 (2-Hydroxyanthraquinone)

3D SDF for NP0138398 (2-Hydroxyanthraquinone)

3D-SDF for NP0138398 (2-Hydroxyanthraquinone)

PDB for NP0138398 (2-Hydroxyanthraquinone)

3D PDB for NP0138398 (2-Hydroxyanthraquinone)

SMILES for NP0138398 (2-Hydroxyanthraquinone)

INCHI for NP0138398 (2-Hydroxyanthraquinone)

Structure for NP0138398 (2-Hydroxyanthraquinone)

3D Structure for NP0138398 (2-Hydroxyanthraquinone)