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Emodin 1-O-beta-D-glucopyranoside

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone Glycoside

Canonical Smiles	OC[C@H]1OC(Oc2cc(O)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21?/m1/s1
InChIKey	HSWIRQIYASIOBE-PMQCEUHXSA-N
Formula	C₂₁H₂₀O₁₀
HBA	10
HBD	6
MW	432.38
Rotatable Bonds	3
TPSA	173.98
LogP	-0.64
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	432.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhamnus prinoides	Rhamnaceae	Plantae	280022

Showing of synonyms

Bezabih M, Abegaz BM. (1998). Glucofrangulin A diacetate from the fruits of Rhamnus prinoides. Bulletin of the Chemical Society of Ethiopia,1998,12(1),45-48. [View] [PubMed]

Pubchem: 163199354

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4

Level: 1

Mol. Weight: 432.38 g/mol

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

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 432.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.88
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.36
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.78
Plasma Protein Binding: 71.96
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 11.31
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.55
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.66
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.86
Micronucleos: Toxic
NR-AhR: Safe
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: -38.63
Rat (Acute): 2.5
Rat (Chronic Oral): 4.2
Fathead Minnow: 4.19
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 577.71
Hydration Free Energy: -8.08
Log(D) at pH=7.4: 0.32
Log(P): 0.85
Log S: -3.45
Log(Vapor Pressure): -11.37
Melting Point: 191.85
pKa Acid: 4.74
pKa Basic: 5.3

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.9688
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.9688
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9148
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9148
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8939
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8939
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8818
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8818
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8700
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8700
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8251
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8251
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8205
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8205
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8201
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8201
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8196
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8196
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8164
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8164
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8123
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8123
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7988
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7988
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7860
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7860
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7856
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7856
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7749
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7749
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7705
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7705
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7688
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7688
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7686
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7686
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7626
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7626
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7538
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7538
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7433
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7433
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7429
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7429
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7344
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7344
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7328
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7328
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7309
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7309
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7299
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7299
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7224
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7224
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7205
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7205
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7173
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7173
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7167
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7167
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7148
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7148
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7108
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7108
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7107
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7107
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7099
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7099
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7084
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7084
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7083
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7083
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7064
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7064
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7040
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7040

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