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Physcion-8-O-rutinoside

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

Canonical Smiles	COc1cc(O[C@@H]2O[C@H](CO[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C
InChI	InChI=1S/C28H32O14/c1-9-4-12-17(14(29)5-9)22(33)18-13(20(12)31)6-11(38-3)7-15(18)41-28-26(37)24(35)21(32)16(42-28)8-39-27-25(36)23(34)19(30)10(2)40-27/h4-7,10,16,19,21,23-30,32,34-37H,8H2,1-3H3/t10-,16+,19-,21+,23+,24-,25+,26+,27+,28+/m0/s1
InChIKey	WQSUUTNUYGPXEC-XIKXQYPFSA-N
Formula	C₂₈H₃₂O₁₄
HBA	14
HBD	7
MW	592.55
Rotatable Bonds	6
TPSA	221.9
LogP	-1.48
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	592.18
Number of Lipinski Rule Violations	3

#	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]

Pubchem: 14630537

Cas: 129393-21-1

Zinc: ZINC000238773829

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3cccc(c34)C(=O)c5c(C4=O)cccc5

Level: 2

Mol. Weight: 592.55 g/mol

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

Level: 1

Mol. Weight: 592.55 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 592.55 g/mol

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

Level: 0

Mol. Weight: 592.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 592.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.58
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.040
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 4.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: 81.18
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.950
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.500
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.790
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.480
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: -8525.010
Rat (Acute): 2.670
Rat (Chronic Oral): 4.270
Fathead Minnow: 19.320
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 472.910
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 0.490
Log(P): 1.03
Log S: -4.05
Log(Vapor Pressure): -11.5
Melting Point: 204.48
pKa Acid: 3.95
pKa Basic: 3.94

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	0.9734
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9226
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8812
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.8695
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8349
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8252
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8251
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8193
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8082
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8029
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.8016
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7970
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7969
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7962
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7962
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7897
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7725
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7636
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7564
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7547
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7528
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7462
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7423
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7401
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7362
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7333
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7325
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7308
Prostaglandin E synthase 2	Q9N0A4	PGES2_MACFA	Macaca fascicularis	3	0.7304
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7292
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7290
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7261
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7260
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7258
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7184
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7159
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7150
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7130
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7123
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7100
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7067
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7066
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7065
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7032
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7018
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7002

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