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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:42:07 UTC

Update Date

2021-09-26 23:13:09 UTC

HMDB ID

HMDB0257042

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Quinizarin

Description

quinizarin belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Based on a literature review a small amount of articles have been published on quinizarin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Quinizarin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Quinizarin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004241519242D          

 18 20  0  0  0  0            999 V2000
    4.2868   -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
    3.5724    1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 10 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257042

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H

> <INCHI_KEY>
GUEIZVNYDFNHJU-UHFFFAOYSA-N

> <FORMULA>
C14H8O4

> <MOLECULAR_WEIGHT>
240.214

> <EXACT_MASS>
240.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.217884376489536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dihydroxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.6115754313333324

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.263523422008376

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.476591772075059

> <JCHEM_PKA_STRONGEST_BASIC>
-5.569823426920412

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
65.11280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quinizarin

> <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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
CONECT   17   13                                                            
CONECT   18   10                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0257042
HETATM    1  O1  UNL     1      -0.080   2.632   0.661  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.055   1.412   0.359  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.380   0.809   0.261  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.496   1.605   0.507  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.752   1.044   0.416  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.943  -0.282   0.089  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.812  -1.070  -0.156  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.553  -0.517  -0.067  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.345  -1.332  -0.322  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.510  -2.539  -0.620  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.004  -0.788  -0.240  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.133  -1.570  -0.483  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.087  -2.886  -0.813  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.410  -0.979  -0.386  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.472   0.342  -0.055  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.360   1.118   0.186  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.472   2.461   0.520  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.094   0.549   0.094  1.00  0.00           C  
HETATM   19  H1  UNL     1       2.332   2.642   0.762  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.638   1.634   0.601  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.921  -0.744   0.013  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.892  -2.114  -0.416  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.340  -3.468  -0.930  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.296  -1.593  -0.577  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.480   0.782   0.015  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.401   2.848   0.580  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4    4    8
CONECT    4    5   19
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   23
CONECT   14   15   15   24
CONECT   15   16   25
CONECT   16   17   18   18
CONECT   17   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dihydroxy-9,10-anthraquinone	ChEBI
1,4-Dihydroxyanthra-9,10-quinone	ChEBI
1,4-Dihydroxyanthrachinon	ChEBI
1,4-Dihydroxyanthraquinone	ChEBI
Chinizarin	ChEBI
Quinizarine	ChEBI
1,4-Dihydroxyanthraquinone, radiacal ion (1-)	MeSH
Anthrarufin	MeSH

Chemical Formula

C₁₄H₈O₄

Average Molecular Weight

240.214

Monoisotopic Molecular Weight

240.042258738

IUPAC Name

1,4-dihydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

quinizarin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H

InChI Key

GUEIZVNYDFNHJU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

dihydroxyanthraquinone (CHEBI:37487 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.98	ALOGPS
logP	3.61	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.11 m³·mol⁻¹	ChemAxon
Polarizability	23.22 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.73	30932474
DeepCCS	[M-H]-	157.339	30932474
DeepCCS	[M-2H]-	190.273	30932474
DeepCCS	[M+Na]+	165.79	30932474
AllCCS	[M+H]+	153.9	32859911
AllCCS	[M+H-H2O]+	150.3	32859911
AllCCS	[M+NH4]+	157.3	32859911
AllCCS	[M+Na]+	158.3	32859911
AllCCS	[M-H]-	150.5	32859911
AllCCS	[M+Na-2H]-	149.8	32859911
AllCCS	[M+HCOO]-	149.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinizarin	OC1=C2C(=O)C3=CC=CC=C3C(=O)C2=C(O)C=C1	3223.9	Standard polar	33892256
Quinizarin	OC1=C2C(=O)C3=CC=CC=C3C(=O)C2=C(O)C=C1	2034.2	Standard non polar	33892256
Quinizarin	OC1=C2C(=O)C3=CC=CC=C3C(=O)C2=C(O)C=C1	2232.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Quinizarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03el-1890000000-f0a4e9ecc3e50ad0abd0	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinizarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinizarin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinizarin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinizarin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinizarin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinizarin 20V, Positive-QTOF	splash10-001i-9420000000-e348d5f5abd2a712ee4b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinizarin 10V, Positive-QTOF	splash10-03di-1930000000-4f70ca9f90b8923fb98e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinizarin 40V, Positive-QTOF	splash10-001i-9200000000-8744a762cecdc552589a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinizarin 10V, Positive-QTOF	splash10-0006-0090000000-8c50e6ba224a5e412ba2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinizarin 20V, Positive-QTOF	splash10-0006-0590000000-16432af6f80b91613c07	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinizarin 40V, Positive-QTOF	splash10-00di-6690000000-2c6d68677d69e2d454bc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinizarin 10V, Negative-QTOF	splash10-000i-0090000000-5e3e7d07adfd2b458c14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinizarin 20V, Negative-QTOF	splash10-000i-0090000000-48e5ef74237af65cce73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinizarin 40V, Negative-QTOF	splash10-052r-2970000000-3209e7f4d86cdcc56262	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6433

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,4-Dihydroxyanthraquinone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

37487

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1279901

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Quinizarin (HMDB0257042)

MOL for HMDB0257042 (Quinizarin)

3D MOL for HMDB0257042 (Quinizarin)

3D SDF for HMDB0257042 (Quinizarin)

3D-SDF for HMDB0257042 (Quinizarin)

PDB for HMDB0257042 (Quinizarin)

3D PDB for HMDB0257042 (Quinizarin)

SMILES for HMDB0257042 (Quinizarin)

INCHI for HMDB0257042 (Quinizarin)

Structure for HMDB0257042 (Quinizarin)

3D Structure for HMDB0257042 (Quinizarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra