NP-MRD: Showing NP-Card for anthrarufin (NP0231097)

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Record Information

Version

2.0

Created at

2022-09-06 11:47:11 UTC

Updated at

2022-09-06 11:47:11 UTC

NP-MRD ID

NP0231097

Secondary Accession Numbers

None

Natural Product Identification

Common Name

anthrarufin

Description

Anthrarufin, also known as az-u or 1,5-dhaq, 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. Anthrarufin is an extremely weak basic (essentially neutral) compound (based on its pKa). anthrarufin was first documented in 1986 (PMID: 3267459). A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5 (PMID: 17971722) (PMID: 18728697) (PMID: 20541965).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004251602562D          

 18 20  0  0  0  0            999 V2000
    5.0013    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
    4.2868    0.8250    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
    5.0013    2.0625    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    1.2375    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
    4.2868    2.4750    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
    3.5724    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
    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
    4.2868    3.3000    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    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
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0231097

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1C(=O)C1=C(C(O)=CC=C1)C2=O

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

> <INCHI_KEY>
JPICKYUTICNNNJ-UHFFFAOYSA-N

> <FORMULA>
C14H8O4

> <MOLECULAR_WEIGHT>
240.214

> <EXACT_MASS>
240.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.213135700602997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dihydroxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.6115754313333324

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.532404983088174

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.914277279274124

> <JCHEM_PKA_STRONGEST_BASIC>
-5.644970719302873

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
65.11280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anthrarufin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   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       2.667   4.620   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11   13                                                  
CONECT    8    4   12   14                                                  
CONECT    9    5   11   15                                                  
CONECT   10    6   12   16                                                  
CONECT   11    7    9   14                                                  
CONECT   12    8   10   13                                                  
CONECT   13    7   12   17                                                  
CONECT   14    8   11   18                                                  
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
1,5-Dihydroxy-9,10-anthracenedione	ChEBI
1,5-Dihydroxy-9,10-anthraquinone	ChEBI
1,5-Dihydroxyanthrachinon	ChEBI
1,5-Dihydroxyanthraquinone	ChEBI
Az-u	ChEBI
1,5-DHAQ	MeSH

Chemical Formula

C₁₄H₈O₄

Average Mass

240.2140 Da

Monoisotopic Mass

240.04226 Da

IUPAC Name

1,5-dihydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

anthrarufin

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1C(=O)C1=C(C(O)=CC=C1)C2=O

InChI Identifier

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

InChI Key

JPICKYUTICNNNJ-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

Not Available

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-4-unsubstituted benzenoid
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:37501 )

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	2.97	ALOGPS
logP	3.61	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.91	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	23.21 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

Not Available

METLIN ID

Not Available

PubChem Compound

8328

PDB ID

Not Available

ChEBI ID

37501

Good Scents ID

Not Available

References

General References

Chairungsi N, Jumpatong K, Suebsakwong P, Sengpracha W, Phutdhawong W, Buddhasukh D: Electrocoagulation of quinone pigments. Molecules. 2006 Jul 14;11(7):514-22. doi: 10.3390/11070514. [PubMed:17971722 ]
Sparks SM, Chen CL, Martin SF: Tandem Intramolecular Benzyne-Furan Cycloadditions. Total Synthesis of Vineomycinone B(2) Methyl Ester. Tetrahedron. 2007 Aug 27;63(35):8619-8635. doi: 10.1016/j.tet.2007.04.031. [PubMed:18728697 ]
Nguyen DD, Jones NC, Hoffmann SV, Spanget-Larsen J: Synchrotron radiation linear dichroism (SRLD) investigation of the electronic transitions of quinizarin, chrysazin, and anthrarufin. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Sep 15;77(1):279-86. doi: 10.1016/j.saa.2010.05.023. Epub 2010 May 24. [PubMed:20541965 ]
Kawai K, Mori H, Sugie S, Yoshimi N, Inoue T, Nakamaru T, Nozawa Y, Matsushima T: Genotoxicity in the hepatocyte/DNA repair test and toxicity to liver mitochondria of 1-hydroxyanthraquinone and several dihydroxyanthraquinones. Cell Biol Toxicol. 1986 Dec;2(4):457-67. doi: 10.1007/BF00117848. [PubMed:3267459 ]
LOTUS database [Link]

Showing NP-Card for anthrarufin (NP0231097)

MOL for NP0231097 (anthrarufin)

3D MOL for NP0231097 (anthrarufin)

3D SDF for NP0231097 (anthrarufin)

3D-SDF for NP0231097 (anthrarufin)

PDB for NP0231097 (anthrarufin)

3D PDB for NP0231097 (anthrarufin)

SMILES for NP0231097 (anthrarufin)

INCHI for NP0231097 (anthrarufin)

Structure for NP0231097 (anthrarufin)

3D Structure for NP0231097 (anthrarufin)