NP-MRD: Showing NP-Card for Purpurin (NP0051635)

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Record Information

Version

1.0

Created at

2022-04-27 22:55:51 UTC

Updated at

2024-05-05 00:32:36 UTC

NP-MRD ID

NP0051635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpurin

Description

Purpurin, also known as alizarin purpurin or c.I. 58205, 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. Purpurin is an extremely weak basic (essentially neutral) compound (based on its pKa). Purpurin is found in Agrobacterium rhizogenes, Asperula odorata , Cinchona ledgeriana, Cinchona pubescens, Galium mollugo, Galium rubioides, Galium spp., Relbunium hypocarpium, Rubia cordifolia , Rubia tinctorum , Rubia wallichiana, Rubia wallichiana DECNE , Senna obtusifolia and Tephrosia purpurea. It was first documented in 1999 (PMID: 10521685). A trihydroxyanthraquinone derived from anthracene by substitution with oxo groups at C-9 and C-10 and with hydroxy groups at C-1, C-2 and C-4 (PMID: 14500876) (PMID: 19748496) (PMID: 20238054) (PMID: 20392152) (PMID: 22997839) (PMID: 20686243).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171504492D          

 19 21  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
  4  5  1  0  0  0  0
  4  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>
NP0051635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8O5/c15-8-5-9(16)14(19)11-10(8)12(17)6-3-1-2-4-7(6)13(11)18/h1-5,15-16,19H

> <INCHI_KEY>
BBNQQADTFFCFGB-UHFFFAOYSA-N

> <FORMULA>
C14H8O5

> <MOLECULAR_WEIGHT>
256.213

> <EXACT_MASS>
256.037173358

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
24.209401615726723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,4-trihydroxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
3.3080101096666663

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.538039790839939

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.593890292891431

> <JCHEM_PKA_STRONGEST_BASIC>
-5.279717987740255

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
67.09370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
purpurin

> <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  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+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  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+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                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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
1,2,4-Trihydroxy-9,10-anthracenedione	ChEBI
1,2,4-Trihydroxy-9,10-anthraquinone	ChEBI
1,2,4-Trihydroxyanthra-9,10-quinone	ChEBI
1,2,4-Trihydroxyanthrachinon	ChEBI
1,2,4-Trihydroxyanthraquinone	ChEBI
Alizarin purpurin	ChEBI
C.I. 58205	ChEBI
Hydroxylizaric acid	ChEBI
Pr	ChEBI
Purpurine	ChEBI
Smoke brown g	ChEBI
Verantin	ChEBI
Hydroxylizarate	Generator
Purpurin, madder root	MeSH

Chemical Formula

C₁₄H₈O₅

Average Mass

256.2130 Da

Monoisotopic Mass

256.03717 Da

IUPAC Name

1,2,4-trihydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

purpurin

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C14H8O5/c15-8-5-9(16)14(19)11-10(8)12(17)6-3-1-2-4-7(6)13(11)18/h1-5,15-16,19H

InChI Key

BBNQQADTFFCFGB-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 201.216488466, C2D6OS, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Agrobacterium rhizogenes	LOTUS Database	35616633
Asperula odorata	Plant	KNApSAcK
Cinchona calisaya	Plant	KNApSAcK
Cinchona pubescens	LOTUS Database	35616633
Galium mollugo	LOTUS Database	35616633
Galium rubioides	LOTUS Database	35616633
Galium spp.	Plant	KNApSAcK
Relbunium hypocarpium	Plant	KNApSAcK
Rubia cordifolia	Plant	KNApSAcK
Rubia tinctorum	Plant	KNApSAcK
Rubia wallichiana	LOTUS Database	35616633
Rubia wallichiana DECNE	Plant	KNApSAcK
Senna obtusifolia	LOTUS Database	35616633
Tephrosia purpurea	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
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

trihydroxyanthraquinone (CHEBI:8645 )
flavanones (C10395 )
Anthraquinone type (C10395 )

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	2.67	ALOGPS
logP	3.31	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.59	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.09 m³·mol⁻¹	ChemAxon
Polarizability	24.21 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

C00002857

Chemspider ID

Not Available

KEGG Compound ID

C10395

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,2,4-Trihydroxyanthraquinone

METLIN ID

Not Available

PubChem Compound

6683

PDB ID

Not Available

ChEBI ID

8645

Good Scents ID

Not Available

References

General References

Marczylo TH, Hayatsu T, Arimoto-Kobayashi S, Tada M, Fujita K, Kamataki T, Nakayama K, Hayatsu H: Protection against the bacterial mutagenicity of heterocyclic amines by purpurin, a natural anthraquinone pigment. Mutat Res. 1999 Aug 18;444(2):451-61. doi: 10.1016/s1383-5718(99)00109-6. [PubMed:10521685 ]
James LC, Tawfik DS: The specificity of cross-reactivity: promiscuous antibody binding involves specific hydrogen bonds rather than nonspecific hydrophobic stickiness. Protein Sci. 2003 Oct;12(10):2183-93. doi: 10.1110/ps.03172703. [PubMed:14500876 ]
Nagashima M, Mawatari K, Tanaka M, Higashi T, Saito H, Muramoto K, Matsukawa T, Koriyama Y, Sugitani K, Kato S: Purpurin is a key molecule for cell differentiation during the early development of zebrafish retina. Brain Res. 2009 Dec 11;1302:54-63. doi: 10.1016/j.brainres.2009.09.020. Epub 2009 Sep 11. [PubMed:19748496 ]
Nagashima M, Saito J, Mawatari K, Mori Y, Matsukawa T, Koriyama Y, Kato S: A hypoplastic retinal lamination in the purpurin knock down embryo in zebrafish. Adv Exp Med Biol. 2010;664:517-24. doi: 10.1007/978-1-4419-1399-9_59. [PubMed:20238054 ]
Kang K, Fong WP, Tsang PW: Novel antifungal activity of purpurin against Candida species in vitro. Med Mycol. 2010 Nov;48(7):904-11. doi: 10.3109/13693781003739351. [PubMed:20392152 ]
Wang K, Chen X, Shan M, Ding A: [Study on intestinal absorption of mollugin and purpurin in rats]. Zhongguo Zhong Yao Za Zhi. 2012 Jun;37(12):1855-8. [PubMed:22997839 ]
Nishimura N, Takai M, Yamamoto E, Hasumi K: Purpurin as a specific inhibitor of spermidine-induced autoactivation of the protease plasma hyaluronan-binding protein. Biol Pharm Bull. 2010;33(8):1430-3. doi: 10.1248/bpb.33.1430. [PubMed:20686243 ]
Grazia C, Clementi C, Miliani C, Romani A: Photophysical properties of alizarin and purpurin Al(III) complexes in solution and in solid state. Photochem Photobiol Sci. 2011 Jul;10(7):1249-54. doi: 10.1039/c1pp05039g. Epub 2011 May 6. [PubMed:21552598 ]
Tsang PW, Bandara HM, Fong WP: Purpurin suppresses Candida albicans biofilm formation and hyphal development. PLoS One. 2012;7(11):e50866. doi: 10.1371/journal.pone.0050866. Epub 2012 Nov 30. [PubMed:23226409 ]
Reddy AL, Nagarajan S, Chumyim P, Gowda SR, Pradhan P, Jadhav SR, Dubey M, John G, Ajayan PM: Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes. Sci Rep. 2012;2:960. doi: 10.1038/srep00960. Epub 2012 Dec 11. [PubMed:23233879 ]

Showing NP-Card for Purpurin (NP0051635)

MOL for NP0051635 (Purpurin)

3D MOL for NP0051635 (Purpurin)

3D SDF for NP0051635 (Purpurin)

3D-SDF for NP0051635 (Purpurin)

PDB for NP0051635 (Purpurin)

3D PDB for NP0051635 (Purpurin)

SMILES for NP0051635 (Purpurin)

INCHI for NP0051635 (Purpurin)

Structure for NP0051635 (Purpurin)

3D Structure for NP0051635 (Purpurin)