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Rhein methylester

Family: Leguminosae/Fabaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone

Canonical Smiles	COC(=O)c1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
InChI	InChI=1S/C16H10O6/c1-22-16(21)7-5-9-13(11(18)6-7)15(20)12-8(14(9)19)3-2-4-10(12)17/h2-6,17-18H,1H3
InChIKey	SGDMEGYCHABPCQ-UHFFFAOYSA-N
Formula	C₁₆H₁₀O₆
HBA	6
HBD	2
MW	298.25
Rotatable Bonds	1
TPSA	100.9
LogP	1.66
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.06
Exact Mass	298.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Senna didymobotrya	Leguminosae/Fabaceae	Plantae	72401

Showing of synonyms

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: 44583637

Zinc: ZINC000040425299

Nmrshiftdb2: 60076850

Chembl: CHEMBL497000

Bindingdb: 50269015

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 208.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.52
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.620
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.840
Plasma Protein Binding: 55.27
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.880
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.080
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.200
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.330
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: 4.640
Rat (Acute): 2.540
Rat (Chronic Oral): 3.200
Fathead Minnow: 4.350
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: 431.740
Hydration Free Energy: -8.890
Log(D) at pH=7.4: 2.880
Log(P): 3.84
Log S: -6.04
Log(Vapor Pressure): -7.34
Melting Point: 210.4
pKa Acid: 6.89
pKa Basic: 3.39

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	0.9600
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.9600
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9437
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9437
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9224
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9224
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9214
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9214
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9186
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9186
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9161
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9161
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9024
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9024
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8985
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8985
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.8775
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.8775
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8759
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8759
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8705
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8705
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.8548
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.8548
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8510
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8510
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8451
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8451
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8448
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8448
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8207
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8207
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8166
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8166
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.8047
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.8047
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8039
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8039
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7919
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7919
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7908
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7908
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7896
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7896
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7763
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7763
Aklanonic acid methyl ester cyclase AcmA	O52646	DNRD_STRGJ	Streptomyces galilaeus	3	0.7610
Aklanonic acid methyl ester cyclase AcmA	O52646	DNRD_STRGJ	Streptomyces galilaeus	3	0.7610
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7602
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7602
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7592
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7592
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7549
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7549
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7535
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7535
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7517
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7517
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7491
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7491
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7473
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7473
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7470
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7470
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7437
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7437
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7369
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7369
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7367
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7367
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7348
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7348
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7336
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7336
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7316
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7316
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7316
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7316
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7312
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7312
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7294
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7294
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7290
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7290
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7283
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7283
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	2	0.7271
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	2	0.7271
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7268
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7268
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7265
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7265
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7243
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7243
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7235
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7235
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7231
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7231
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7217
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7217
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7214
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7214
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7196
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7196
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7178
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7178
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7177
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7177
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7152
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7152
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7143
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7143
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7130
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7130
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7117
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7117
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7100
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7100
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7100
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7100
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7098
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7098
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7075
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7075
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7070
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7070
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7051
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7051
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7003
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7003

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