Rhein - Compound Card

Rhein

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Rhein

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1O)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)
InChIKey FCDLCPWAQCPTKC-UHFFFAOYSA-N
Formula C15H8O6
HBA 5
HBD 3
MW 284.22
Rotatable Bonds 1
TPSA 111.9
LogP 1.57
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 284.03
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senna floribunda Leguminosae/Fabaceae Plantae 2601732
2 Senna Didymobotrya Leguminosae/Fabaceae Plantae 72401

Showing of synonyms

  • Tsegaye G, Alemayehu G. (2006). Phytochemical investigation on the stem bark of Senna floribunda. M.Sc. Thesis, Addis Ababa University, Ethiopia,2006. [View] [PubMed]
  • Alemayehu G, Abegaz B, et al. (1989). Quinones of Senna Didymobotrya.. Bulletin of the Chemical Society of Ethiopia,1989,3(1),37-40. [View] [PubMed]
Pubchem: 10168
Kegg Ligand: C10401
Chebi: 8825
Nmrshiftdb2: 60025881
Drugbank: DB13174
Pdb Ligand: RHN
Bindingdb: 32021
CPRiL: 98272
Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 284.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.780
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.080
Plasma Protein Binding
61.51
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.240
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.140
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.020
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.060
Rat (Acute)
2.340
Rat (Chronic Oral)
3.620
Fathead Minnow
4.070
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
448.780
Hydration Free Energy
-9.260
Log(D) at pH=7.4
-0.340
Log(P)
3.52
Log S
-4.1
Log(Vapor Pressure)
-8.01
Melting Point
281.78
pKa Acid
7.32
pKa Basic
2.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9583
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9583
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9195
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9195
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9147
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9147
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9108
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9108
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9046
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9046
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8960
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8960
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8910
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8910
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8817
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8817
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8779
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8779
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8758
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8758
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8666
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8666
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8497
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8434
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8434
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8428
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8428
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8424
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8424
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.8373
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.8373
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8188
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8188
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8056
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8056
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7984
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7984
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7900
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7900
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7752
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7752
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7697
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7697
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7575
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7575
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7555
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7555
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7540
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7540
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7520
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7520
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7500
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7500
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 3 0.7483
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 3 0.7483
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7474
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7474
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7468
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7468
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7447
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7447
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7442
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7442
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7365
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7365
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7348
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7348
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7344
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7344
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7332
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7332
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7310
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7310
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7289
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7289
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7282
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7282
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.7274
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.7274
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7273
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7273
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7240
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7240
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7228
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7228
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7209
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7209
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7183
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7183
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7170
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7170
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7152
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7152
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7094
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7094
Tyrosyl-DNA phosphodiesterase 2 Q9JJX7 TYDP2_MOUSE Mus musculus 2 0.7070
Tyrosyl-DNA phosphodiesterase 2 Q9JJX7 TYDP2_MOUSE Mus musculus 2 0.7070
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7067
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7067
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7055
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7055
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7034
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7034
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7032
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7032

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