NP-MRD: Showing NP-Card for Rhein (NP0047481)

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Record Information

Version

2.0

Created at

2022-03-17 20:40:55 UTC

Updated at

2025-02-11 15:44:07 UTC

NP-MRD ID

NP0047481

Natural Product DOI

https://doi.org/10.57994/1341

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhein

Description

Rhein, also known as cassic acid or dipropionyl rhein, belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Thus, rhein is considered to be an aromatic polyketide lipid molecule. Rhein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Rhein has been detected, but not quantified in, a few different foods, such as docks, garden rhubarbs, and green vegetables. Rhein is found in Cassia acutifolia , Cassia alata L. , Cassia angustifolia , Cassia fistula, Cassia javanica, Cassia mimosoides , Cassia senna , Cassia sieberiana, Cassia tora , Ephedra sinica , Haplopappus baylatum, Hemerocallis fulva , Hemerocallis thunbergii, Hemerocallus minor, Kniphofia aloides, Muehlenbeckia hastulata, Muehlenbeckia tamnifolia , Polygonum cuspidatum , Polygonum multiflorum , Rheum emodi , Rheum nobile, Rheum officinale , Rheum palmatum , Rheum spp., Rheum tanguticum , Rumex acetosa , Rumex acetosella , Rumex confertus , Rumex crispus , Rumex cristatus, Rumex hydrolapathum, Rumex nepalensis , Rumex obtusifolius , Rumex spp., Ruta graveolens , Scrophularia nodosa , Senna alata, Senna alexandrina, Senna didymobotrya and Senna reticulata. Rhein was first documented in 1994 (PMID: 7972313). This could make rhein a potential biomarker for the consumption of these foods (PMID: 12749897) (PMID: 9690877) (PMID: 14765286) (PMID: 22007260).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061306462D          

 21 23  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
    4.2868    0.8250    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
    1.4289    0.8250    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
    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    1.2375    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    2.4750    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    2.0625    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
    0.0000    0.8250    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    3.3000    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
    0.0000    0.0000    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  2  0  0  0  0
 10  5  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  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)

> <INCHI_KEY>
FCDLCPWAQCPTKC-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.2204

> <EXACT_MASS>
284.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.620896626424145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
3.269158339333333

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.088754562545892

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3988243915354075

> <JCHEM_PKA_STRONGEST_BASIC>
-4.446915529565238

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
72.369

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
monorhein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   2.310   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   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   2.310   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   4.620   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   3.850   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    9                                                       
CONECT    4    6    8                                                       
CONECT    5    6   10                                                       
CONECT    6    4    5   15                                                  
CONECT    7    2   11   13                                                  
CONECT    8    4   12   13                                                  
CONECT    9    3   11   16                                                  
CONECT   10    5   12   17                                                  
CONECT   11    7    9   14                                                  
CONECT   12    8   10   14                                                  
CONECT   13    7    8   18                                                  
CONECT   14   11   12   19                                                  
CONECT   15    6   20   21                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
1,8-Dihydroxy-3-carboxyl anthraquinone	HMDB
1,8-Dihydroxy-3-carboxyl-9,10-anthraquinone	HMDB
1,8-Dihydroxyanthraquinone-3-carboxylic acid	HMDB
4, 5-Dihydroxyanthraquinone-2-carboxylic acid	HMDB
4,5-Dihydroxy-2-anthraquinonecarboxylic acid	HMDB
4,5-DiOH-anthraquinone-2-COOH	HMDB
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9ci	HMDB
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid	HMDB
Cassic acid	HMDB
Chrysazin-3-carboxylic acid	HMDB
Dipropionyl rhein	HMDB
Monorhein	HMDB
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)	HMDB
Rhubarb yellow	HMDB
4,5-Dihydroxyanthraquinone-2-carboxylic acid	HMDB

Chemical Formula

C₁₅H₈O₆

Average Mass

284.2204 Da

Monoisotopic Mass

284.03209 Da

IUPAC Name

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

monorhein

CAS Registry Number

478-43-3

SMILES

OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)

InChI Key

FCDLCPWAQCPTKC-UHFFFAOYSA-N

Experimental Spectra

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

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, C2D6OS, 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
Cassia acutifolia	Plant	KNApSAcK
Cassia alata L.	Plant	KNApSAcK
Cassia angustifolia	Plant	KNApSAcK
Cassia fistula	LOTUS Database	35616633
Cassia javanica	LOTUS Database	35616633
Cassia mimosoides	Plant	KNApSAcK
Cassia senna	Plant	KNApSAcK
Cassia sieberiana	LOTUS Database	35616633
Cassia tora	Plant	KNApSAcK
Ephedra sinica	Plant	KNApSAcK
Haplopappus baylatum	Plant	KNApSAcK
Hemerocallis fulva	Plant	KNApSAcK
Hemerocallis thunbergii	Plant	KNApSAcK
Hemerocallus minor	-	KNApSAcK
Kniphofia aloides	Plant	KNApSAcK
Muehlenbeckia hastulata	Plant	KNApSAcK
Muehlenbeckia tamnifolia	Plant	KNApSAcK
Polygonum cuspidatum	Plant	KNApSAcK
Polygonum multiflorum	Plant	KNApSAcK
Rheum australe	Plant	KNApSAcK
Rheum nobile	LOTUS Database	35616633
Rheum officinale	Plant	KNApSAcK
Rheum palmatum	Plant	KNApSAcK
Rheum rhabarbarum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rheum spp.	Plant	KNApSAcK
Rheum tanguticum	Plant	KNApSAcK
Rumex	FooDB	KNAPSACK
Rumex acetosa	Plant	KNApSAcK
Rumex acetosella	Plant	KNApSAcK
Rumex confertus	Plant	KNApSAcK
Rumex crispus	Plant	KNApSAcK
Rumex cristatus	LOTUS Database	35616633
Rumex hydrolapathum	Plant	KNApSAcK
Rumex nepalensis	Plant	KNApSAcK
Rumex obtusifolius	Plant	KNApSAcK
Rumex spp.	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Scrophularia nodosa	Plant	KNApSAcK
Senna alata	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Senna didymobotrya	LOTUS Database	35616633
Senna reticulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:8825 )
Anthracenes and phenanthrenes (C10401 )
Anthraquinone type (C10401 )
Anthracenes and phenanthrenes (LMPK13040015 )

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	2.18	ALOGPS
logP	3.27	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.37 m³·mol⁻¹	ChemAxon
Polarizability	26.62 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

HMDB0032876

DrugBank ID

DB13174

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rhein

METLIN ID

Not Available

PubChem Compound

10168

PDB ID

RHN

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Didry N, Dubreuil L, Pinkas M: Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Pharmazie. 1994 Sep;49(9):681-3. [PubMed:7972313 ]
Stermitz FR, Cashman KK, Halligan KM, Morel C, Tegos GP, Lewis K: Polyacylated neohesperidosides from Geranium caespitosum: bacterial multidrug resistance pump inhibitors. Bioorg Med Chem Lett. 2003 Jun 2;13(11):1915-8. doi: 10.1016/s0960-894x(03)00316-0. [PubMed:12749897 ]
Izzo AA, Mascolo N, Capasso F: Effect of sodium rhein on electrically-evoked and agonist-induced contractions of the guinea-pig isolated ileal circular muscle. Br J Pharmacol. 1998 Jun;124(4):825-31. doi: 10.1038/sj.bjp.0701900. [PubMed:9690877 ]
Kuo PL, Hsu YL, Ng LT, Lin CC: Rhein inhibits the growth and induces the apoptosis of Hep G2 cells. Planta Med. 2004 Jan;70(1):12-6. doi: 10.1055/s-2004-815448. [PubMed:14765286 ]
Chang CY, Chan HL, Lin HY, Way TD, Kao MC, Song MZ, Lin YJ, Lin CW: Rhein induces apoptosis in human breast cancer cells. Evid Based Complement Alternat Med. 2012;2012:952504. doi: 10.1155/2012/952504. Epub 2011 Oct 5. [PubMed:22007260 ]

Showing NP-Card for Rhein (NP0047481)

MOL for NP0047481 (Rhein)

3D MOL for NP0047481 (Rhein)

3D SDF for NP0047481 (Rhein)

3D-SDF for NP0047481 (Rhein)

PDB for NP0047481 (Rhein)

3D PDB for NP0047481 (Rhein)

SMILES for NP0047481 (Rhein)

INCHI for NP0047481 (Rhein)

Structure for NP0047481 (Rhein)

3D Structure for NP0047481 (Rhein)