Rhein

Details

• Internal ID: 7e630060-29c3-495b-be9f-0b8284b2be13
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• SMILES (Canonical): C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)C(=O)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)C(=O)O
• InChI: 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
• Popularity: 940 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₈O₆
• Molecular Weight: 284.22 g/mol
• Exact Mass: 284.03208797 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 478-43-3
• Monorhein
• Rhubarb Yellow
• Rheic acid
• Cassic acid
• 4,5-Dihydroxyanthraquinone-2-carboxylic acid
• 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• Chrysazin-3-carboxylic acid
• 1,8-Dihydroxy-3-carboxyanthraquinone
• Rheinic acid
• NSC 38629
• 1,8-Dihydroxyanthraquinone-3-carboxylic acid
• dipropionyl rhein
• 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
• 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
• C15H8O6
• MFCD00009618
• CCRIS 5129
• EINECS 207-521-4
• Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)
• UNII-YM64C2P6UX
• BRN 2222155
• YM64C2P6UX
• MLS000069639
• CHEBI:8825
• 2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
• 4,5-Dihydroxy-2-anthraquinonecarboxylic acid
• DTXSID4026000
• 4,5-DiOH-anthraquinone-2-COOH
• 9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• NSC-38629
• SMR000058210
• 1,8-DIHYDROXY-3-CARBOXYL ANTHRAQUINONE
• 4-10-00-04088 (Beilstein Handbook Reference)
• 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid
• Rhein(Monorhein)
• Rhein - Monorhein
• RHN
• Rhein,(S)
• Rhein; Rhubarb Yellow
• Rhein, technical grade
• 4ie7
• ST057726
• regid855879
• RHEIN [INCI]
• RHEIN [MI]
• Rhein, analytical standard
• 1,8-dihydroxy-3-carboxyl-9,10-anthraquinone
• D0M2TY
• SCHEMBL25253
• US9238626, Rhein
• cid_10168
• MLS006011744
• CHEMBL418068
• DTXCID606000
• MEGxp0_001866
• 4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
• ACon1_000217
• BDBM32021
• BCP28202
• HY-N0105
• NSC38629
• Tox21_201098
• 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylicacid
• BBL009695
• C15-H8-O6
• LMPK13040015
• LS-129
• s2400
• STL141046
• AKOS005259272
• AC-7978
• CS-5239
• CS-T-41737
• DB13174
• NCGC00018199-01
• NCGC00018199-02
• NCGC00018199-03
• NCGC00018199-04
• NCGC00018199-05
• NCGC00018199-06
• NCGC00018199-07
• NCGC00023342-03
• NCGC00023342-04
• NCGC00258650-01
• AM807834
• AS-11635
• CAS-478-43-3
• SY051290
• D3986
• FT-0645050
• FT-0674401
• 4, 5-Dihydroxyanthraquinone-2-carboxylic acid
• 2-Anthraquinonecarboxylic acid, 4,5-dihydroxy-
• EN300-303248
• DIHYDROXY-3-CARBOXYLANTHRAQUINONE, 1,8-
• A827360
• Q720356
• Q-100512
• 4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
• 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylicacid
• BRD-K27335680-001-01-9
• 2-Anthroic acid,10-dihydro-4,5-dihydroxy-9,10-dioxo-
• 4,5-dihydroxy-9,10-diketo-anthracene-2-carboxylic acid
• 2-Anthracenecarboxylic acid,10-dihydro-4,5-dihydroxy-9,10-dioxo-
• 4,5-bis(oxidanyl)-9,10-bis(oxidanylidene)anthracene-2-carboxylic acid
• 4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid #
• 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracene carboxylic acid
• 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	+	0.6309	63.09%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8383	83.83%
OATP2B1 inhibitior	-	0.6923	69.23%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9275	92.75%
MATE1 inhibitior	-	0.5800	58.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8732	87.32%
P-glycoprotein inhibitior	-	0.9711	97.11%
P-glycoprotein substrate	-	0.9363	93.63%
CYP3A4 substrate	-	0.6398	63.98%
CYP2C9 substrate	-	0.8352	83.52%
CYP2D6 substrate	-	0.8880	88.80%
CYP3A4 inhibition	-	0.9258	92.58%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	-	0.9233	92.33%
CYP2D6 inhibition	-	0.8680	86.80%
CYP1A2 inhibition	-	0.6497	64.97%
CYP2C8 inhibition	-	0.7814	78.14%
CYP inhibitory promiscuity	-	0.9220	92.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7836	78.36%
Carcinogenicity (trinary)	Non-required	0.5028	50.28%
Eye corrosion	-	0.9916	99.16%
Eye irritation	+	0.9629	96.29%
Skin irritation	+	0.7101	71.01%
Skin corrosion	-	0.9873	98.73%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8970	89.70%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8125	81.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.7000	70.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	II	0.4905	49.05%
Estrogen receptor binding	+	0.5490	54.90%
Androgen receptor binding	+	0.5993	59.93%
Thyroid receptor binding	-	0.7910	79.10%
Glucocorticoid receptor binding	+	0.7008	70.08%
Aromatase binding	-	0.6632	66.32%
PPAR gamma	+	0.7141	71.41%
Honey bee toxicity	-	0.9547	95.47%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.9884	98.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	15848.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	125892.5 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	35481.3 nM	Potency	via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	17000 nM	IC50	PMID: 24568372
CHEMBL4801	P29466	Caspase-1	31622.8 nM; 25118.9 nM; 39810.7 nM; 25118.9 nM; 15848.9 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL3468	P55210	Caspase-7	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	11220.2 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	12589.3 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	10000 nM; 17782.8 nM; 17782.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	12589.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	2818.4 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	28183.8 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	501.2 nM; 501.2 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	96.53%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.15%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.20%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.13%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.95%	91.11%
CHEMBL1811	P34995	Prostanoid EP1 receptor	88.90%	95.71%
CHEMBL2535	P11166	Glucose transporter	87.98%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.78%	89.00%
CHEMBL3194	P02766	Transthyretin	86.80%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.19%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.56%	93.40%
CHEMBL340	P08684	Cytochrome P450 3A4	83.40%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.43%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	80.47%	94.73%

Plants that contains it

• Aconitum seravschanicum
• Adansonia grandidieri
• Albizia myriophylla
• Alkekengi officinarum
• Aloe africana
• Aloe ferox
• Aloe spicata
• Aloe vera
• Amphorogyne spicata
• Anaphalis lactea
• Anchusa azurea
• Aphyllocladus denticulatus
• Balanophora laxiflora
• Bassia muricata
• Benincasa hispida
• Carduus tenuiflorus
• Cassia fistula
• Cassia javanica
• Cassia sieberiana
• Chaiturus marrubiastrum
• Chamaecrista mimosoides
• Cryptochilus strictus
• Degenia velebitica
• Delphinium nuttallianum
• Delphinium virgatum
• Dendriopoterium menendezii
• Dendrobium chrysanthum
• Dendrobium chrysotoxum
• Dendrobium fimbriatum
• Dendrobium loddigesii
• Dendrobium moniliforme
• Dendrobium nobile
• Dianthera secunda
• Dillenia indica
• Dipsacus dipsacoides
• Dodonaea viscosa
• Dysoxylum cumingianum
• Enceliopsis argophylla
• Erythrophleum ivorense
• Flacourtia jangomas
• Galatella sedifolia subsp. sedifolia
• Grangea maderaspatana
• Helichrysum chionosphaerum
• Hemerocallis fulva
• Jacquemontia paniculata
• Lavandula angustifolia subsp. pyrenaica
• Leptocereus quadricostatus
• Lespedeza tomentosa
• Lupinus argenteus subsp. argenteus
• Mandragora officinarum
• Metrodorea nigra
• Miliusa velutina
• Neobalanocarpus heimii
• Nepeta granatensis
• Onobrychis arenaria
• Oplopanax elatus
• Petunia inflata
• Phedimus selskanianus
• Photinia serratifolia
• Pittocaulon praecox
• Prunella vulgaris
• Psychotria stachyoides
• Quercus rubra
• Reynoutria japonica
• Reynoutria multiflora
• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rheum racemiferum
• Rheum rhabarbarum
• Rheum ribes
• Rheum tanguticum
• Rosa villosa
• Rumex cristatus
• Ruta graveolens
• Salvia greggii
• Senecio behnii
• Senecio subdentatus
• Senna alata
• Senna alexandrina
• Senna didymobotrya
• Senna obtusifolia
• Senna podocarpa
• Senna reticulata
• Senna tora
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Teucrium yemense
• Trichotosia mollis
• Verbascum densiflorum
• Vitex negundo

Cross-Links

• PubChem: 10168
• NPASS: NPC288089
• ChEMBL: CHEMBL418068
• LOTUS: LTS0275952
• wikiData: Q720356