RHN

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

Created:	2011-03-15
Last modified:	2020-06-05

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3 entries where RHN is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	29
Chiral Atom Count	0
Bond Count	31
Aromatic Bond Count	12

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Chemical Component Summary
Name	4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Synonyms	Rhein; Rhubarb Yellow
Systematic Name (OpenEye OEToolkits)	4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
Formula	C₁₅ H₈ O₆
Molecular Weight	284.22
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(O)c3cc2C(=O)c1cccc(O)c1C(=O)c2c(O)c3
SMILES	CACTVS	3.370	OC(=O)c1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1
SMILES	OpenEye OEToolkits	1.7.0	c1cc2c(c(c1)O)C(=O)c3c(cc(cc3O)C(=O)O)C2=O
Canonical SMILES	CACTVS	3.370	OC(=O)c1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1
Canonical SMILES	OpenEye OEToolkits	1.7.0	c1cc2c(c(c1)O)C(=O)c3c(cc(cc3O)C(=O)O)C2=O
InChI	InChI	1.03	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)
InChIKey	InChI	1.03	FCDLCPWAQCPTKC-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB13174
Name	Rhein
Groups	experimental
Description	Rhein is an anthraquinone metabolite of rheinanthrone and senna glycoside is present in many medicinal plants including Rheum palmatum, Cassia tora, Polygonum multiflorum, and Aloe barbadensis [A19247]. It is known to have hepatoprotective, nephroprotective, anti-cancer, anti-inflammatory, and several other protective effects.
Synonyms	Rhein
Indication	No approved indication.
Categories	Anthracenes Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (weak) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (weak) Cytochrome P-450 Enzyme Inhibitors Enzyme Inhibitors NADH, NADPH Oxidoreductases, antagonists & inhibitors Quinones
CAS number	478-43-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Heat shock protein HSP 90-alpha	MPEETQTQDQPMEEEEVETFAFQAEIAQLMSLIINTFYSNKEIFLRELIS...	unknown	inhibitor
Oxysterols receptor LXR-alpha	MSLWLGAPVPDIPPDSAVELWKPGAQDASSQAQGGSSCILREEARMPHSA...	unknown	inhibitor
Oxysterols receptor LXR-beta	MSSPTTSSLDTPLPGNGPPQPGAPSSSPTVKEEGPEPWPGGPDPDVPGTD...	unknown	inhibitor
Arylamine N-acetyltransferase	-	unknown	inhibitor
Polyunsaturated fatty acid 5-lipoxygenase	MPSYTVTVATGSQWFAGTDDYIYLSLVGSAGCSEKHLLDKPFYNDFERGA...	unknown	inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	inhibitor
Cytochrome P450 3A Subfamily	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682