NP-MRD: Showing NP-Card for 1,3-Dihydroxy-2-methyl-9,10-anthraquinone (NP0051639)

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Record Information

Version

2.0

Created at

2022-04-27 22:55:57 UTC

Updated at

2022-04-27 22:55:57 UTC

NP-MRD ID

NP0051639

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-Dihydroxy-2-methyl-9,10-anthraquinone

Description

Rubiadin 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-Dihydroxy-2-methyl-9,10-anthraquinone is found in Cinchona ledgeriana, Cinchona pubescens, Coelospermum paniculatum, Commitheca liebrechtsiana, Coprosma linariifolia Hook.f., Coprosma lucida, Coprosma robusta , Coprosma rotundifolia, Coprosma spp., Coprosma tenuicaulis, Hedyotis capitellata , Faramea occidentalis, Galium aparine, Galium rubioides, Galium spp., Galium verum, Gynochthodes jasminoides, Morinda umbellata, Oldenlandia hedyotidea, Heterophyllaea pustulata, Hymenodictyon excelsum , Hymenodictyon orixense, Morinda angustifolia, Morinda citrifolia , Morinda officinalis , Morinda pandurifolia, Morinda tinctoria var.tomentosa. , Ophiorrhiza hayatana, Plocama pendula, Prismatomeris fragrans, Prismatomeris sessiliflora, Prismatomeris tetrandra, Proclema pendula, Rennellia elliptica, Rubia cordifolia , Rubia lanceolata, Rubia tinctorum , Rubia wallichiana, Rubia wallichiana DECNE , Rubia yunnanensis and Tectona grandis . 1,3-Dihydroxy-2-methyl-9,10-anthraquinone was first documented in 1997 (PMID: 9425750). Rubiadin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 10410466) (PMID: 16213120) (PMID: 19793347) (PMID: 20965744) (PMID: 22822668) (PMID: 24062780).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.0848   -0.5338    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581   -0.2775    0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    0.0834   -0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1711    0.2074   -1.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7738    0.3203   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.2059   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343   -0.1593    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5847   -0.3977    1.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5694   -0.7591    2.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945   -0.2772    1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158   -0.6038    2.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078   -0.0184    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -0.1328    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4934    0.1094    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4263    0.4767   -1.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    0.5899   -1.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274    0.3453   -1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6960    0.4630   -1.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6032    0.7945   -2.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9040   -0.9208    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    0.4368    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9053   -1.2417    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264    0.4652   -2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147    0.6054   -2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9075   -0.9276    3.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -0.4170    1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4967    0.0212    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3210    0.6653   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008    0.8769   -2.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  7  6  1  0
 12 17  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
 16 29  1  0
 15 28  1  0
 14 27  1  0
 13 26  1  0
  9 25  1  0
M  END


  Mrv1533004171513102D          

 19 21  0  0  0  0            999 V2000
    0.7145   -2.8875    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
    1.4289   -1.6500    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c1-7-11(16)6-10-12(13(7)17)15(19)9-5-3-2-4-8(9)14(10)18/h2-6,16-17H,1H3

> <INCHI_KEY>
IRZTUXPRIUZXMP-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.241

> <EXACT_MASS>
254.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.537984217669567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
3.474996820666666

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.320114277849258

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.810127622375624

> <JCHEM_PKA_STRONGEST_BASIC>
-5.335470634745806

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
70.15400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rubiadin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   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  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6   18                                                  
CONECT   18   17    2   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
1,3-Dihydroxy-2-methyl-9,10-anthracenedione	MeSH

Chemical Formula

C₁₅H₁₀O₄

Average Mass

254.2410 Da

Monoisotopic Mass

254.05791 Da

IUPAC Name

1,3-dihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

rubiadin

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C15H10O4/c1-7-11(16)6-10-12(13(7)17)15(19)9-5-3-2-4-8(9)14(10)18/h2-6,16-17H,1H3

InChI Key

IRZTUXPRIUZXMP-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cinchona calisaya	Plant	KNApSAcK
Cinchona pubescens	LOTUS Database	35616633
Coelospermum paniculatum	LOTUS Database	35616633
Commitheca liebrechtsiana	-	KNApSAcK
Coprosma linariifolia	Plant	KNApSAcK
Coprosma lucida	LOTUS Database	35616633
Coprosma robusta	Plant	KNApSAcK
Coprosma rotundifolia	Plant	KNApSAcK
Coprosma spp.	Plant	KNApSAcK
Coprosma tenuicaulis	Plant	KNApSAcK
Dimetia capitellata	Plant	KNApSAcK
Faramea occidentalis	LOTUS Database	35616633
Galium aparine	LOTUS Database	35616633
Galium rubioides	LOTUS Database	35616633
Galium spp.	Plant	KNApSAcK
Galium verum	LOTUS Database	35616633
Gynochthodes jasminoides	LOTUS Database	35616633
Gynochthodes umbellata	Plant	KNApSAcK
Hedyotis hedyotidea	LOTUS Database	35616633
Heterophyllaea pustulata	LOTUS Database	35616633
Hymenodictyon excelsum	Plant	KNApSAcK
Hymenodictyon orixense	LOTUS Database	35616633
Morinda angustifolia	LOTUS Database	35616633
Morinda citrifolia	Plant	KNApSAcK
Morinda officinalis	Plant	KNApSAcK
Morinda pandurifolia	Plant	KNApSAcK
Morinda tinctoria var.tomentosa.	Plant	KNApSAcK
Ophiorrhiza hayatana	LOTUS Database	35616633
Plocama pendula	Plant	KNApSAcK
Prismatomeris fragrans	LOTUS Database	35616633
Prismatomeris sessiliflora	LOTUS Database	35616633
Prismatomeris tetrandra	Plant	KNApSAcK
Proclema pendula	-	KNApSAcK
Rennellia elliptica	LOTUS Database	35616633
Rubia cordifolia	Plant	KNApSAcK
Rubia lanceolata	LOTUS Database	35616633
Rubia tinctorum	Plant	KNApSAcK
Rubia wallichiana	LOTUS Database	35616633
Rubia wallichiana DECNE	Plant	KNApSAcK
Rubia yunnanensis	Plant	KNApSAcK
Tectona grandis	Plant	KNApSAcK

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-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:69533 )
Anthraquinone type (C10402 )

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	3.08	ALOGPS
logP	3.47	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-5.3	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	70.15 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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

C00002862

Chemspider ID

Not Available

KEGG Compound ID

C10402

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rubiadin

METLIN ID

Not Available

PubChem Compound

124062

PDB ID

Not Available

ChEBI ID

69533

Good Scents ID

Not Available

References

General References

Tripathi YB, Sharma M: Comparison of the antioxidant action of the alcoholic extract of Rubia cordifolia with rubiadin. Indian J Biochem Biophys. 1998 Oct;35(5):313-6. [PubMed:10410466 ]
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Inoue K, Yoshida M, Takahashi M, Fujimoto H, Shibutani M, Hirose M, Nishikawa A: Carcinogenic potential of alizarin and rubiadin, components of madder color, in a rat medium-term multi-organ bioassay. Cancer Sci. 2009 Dec;100(12):2261-7. doi: 10.1111/j.1349-7006.2009.01342.x. Epub 2009 Sep 2. [PubMed:19793347 ]
Comini LR, Montoya SC, Paez PL, Arguello GA, Albesa I, Cabrera JL: Antibacterial activity of anthraquinone derivatives from Heterophyllaea pustulata (Rubiaceae). J Photochem Photobiol B. 2011 Feb 7;102(2):108-14. doi: 10.1016/j.jphotobiol.2010.09.009. Epub 2010 Sep 29. [PubMed:20965744 ]
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Bussmann RW, Hennig L, Giannis A, Ortwein J, Kutchan TM, Feng X: Anthraquinone Content in Noni (Morinda citrifolia L.). Evid Based Complement Alternat Med. 2013;2013:208378. doi: 10.1155/2013/208378. Epub 2013 Aug 26. [PubMed:24062780 ]
Tripathi YB, Sharma M, Manickam M: Rubiadin, a new antioxidant from Rubia cordifolia. Indian J Biochem Biophys. 1997 Jun;34(3):302-6. [PubMed:9425750 ]

Showing NP-Card for 1,3-Dihydroxy-2-methyl-9,10-anthraquinone (NP0051639)

MOL for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

3D MOL for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

3D SDF for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

3D-SDF for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

PDB for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

3D PDB for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

SMILES for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

INCHI for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

Structure for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)

3D Structure for NP0051639 (1,3-Dihydroxy-2-methyl-9,10-anthraquinone)