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1,2,6,8-tetrahydroxy-3 methyl anthraquinone 8-O-beta-D-glucopyranoside

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

Canonical Smiles	OC[C@@H]1O[C@H](Oc2cc(O)cc3c2C(=O)c2c(C3=O)cc(c(c2O)O)C)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C21H20O11/c1-6-2-8-13(18(28)14(6)24)17(27)12-9(15(8)25)3-7(23)4-10(12)31-21-20(30)19(29)16(26)11(5-22)32-21/h2-4,11,16,19-24,26,28-30H,5H2,1H3/t11-,16-,19+,20-,21-/m0/s1
InChIKey	NHKCWTLRPTZPQY-KQIVYZGFSA-N
Formula	C₂₁H₂₀O₁₁
HBA	11
HBD	7
MW	448.38
Rotatable Bonds	3
TPSA	194.21
LogP	-0.93
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	448.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhamnus alaternus	Rhamnaceae	Plantae	280017

Showing of synonyms

Ben Ammar R, Miyamoto T, et al. (2019). Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity. Natural product research,2019, 33(2), 280-286. [View] [PubMed]

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 448.38 g/mol

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

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.460
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 78.26
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: 12.760
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.090
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.840
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.300
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: -61.210
Rat (Acute): 2.450
Rat (Chronic Oral): 4.330
Fathead Minnow: 4.020
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: 598.270
Hydration Free Energy: -5.580
Log(D) at pH=7.4: -0.120
Log(P): 0.71
Log S: -4.12
Log(Vapor Pressure): -11.82
Melting Point: 207.34
pKa Acid: 4.05
pKa Basic: 6.02

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	0.9668
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.9015
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8867
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8667
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8497
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8337
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8281
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8261
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8197
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8194
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8166
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8052
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8038
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8031
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8014
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7961
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7947
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7747
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7730
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7681
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7670
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7618
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7514
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7461
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7432
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7358
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7344
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7314
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7307
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7184
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7136
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7131
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7096
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7091
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7020

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