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Isoorientin 2''-O-beta-D-xylopyranoside

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: C-Glycosyl Flavone

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(O)cc3c(c2O)c(=O)cc(o3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@H]1OC[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C26H28O16/c27-6-16-19(34)21(36)24(42-25-22(37)18(33)13(32)7-38-25)26(40-16)41-23-12(31)5-15-17(20(23)35)11(30)4-14(39-15)8-1-2-9(28)10(29)3-8/h1-5,13,16,18-19,21-22,24-29,31-37H,6-7H2/t13-,16+,18+,19+,21-,22-,24+,25+,26-/m0/s1
InChIKey	HWMXTDMNEJFWMS-RFSNSKQYSA-N
Formula	C₂₆H₂₈O₁₆
HBA	16
HBD	10
MW	596.49
Rotatable Bonds	6
TPSA	269.43
LogP	-2.08
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	596.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Joannesia princeps	Euphorbiaceae	Plantae	179690

Showing of synonyms

Camero C, Temraz A, et al. (2017). Phytochemical study of Joannesia princeps Vell. (Euphorbiaceae) leaves.. Biochemical Systematics and Ecology, 2017, 70, 69-72. [View]

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 596.49 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 596.49 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)OC4CCCCO4

Level: 2

Mol. Weight: 596.49 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)OC3CCCCO3

Level: 1

Mol. Weight: 596.49 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 596.49 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 596.49 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 596.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 596.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 596.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.710
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 7.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.690
Plasma Protein Binding: 64.98
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: 13.720
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.430
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.700
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.320
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: -9341.960
Rat (Acute): 2.330
Rat (Chronic Oral): 4.520
Fathead Minnow: 19.250
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 546.210
Hydration Free Energy: -3.000
Log(D) at pH=7.4: -0.700
Log(P): -0.85
Log S: -4.24
Log(Vapor Pressure): -12.08
Melting Point: 217.9
pKa Acid: 3.06
pKa Basic: 7.91

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9616
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9382
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9191
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9012
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8997
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8800
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8688
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8581
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8565
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8550
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8504
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8504
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8489
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8428
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8344
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8314
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8309
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8137
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8133
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8102
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8070
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8023
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8008
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7979
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7911
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7891
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7876
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7826
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7802
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7717
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7693
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7677
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7647
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7490
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7447
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	3	0.7414
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7374
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7353
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7351
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7316
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7313
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7297
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7291
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7287
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7286
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7280
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7278
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7275
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Q9WY79	MURE_THEMA	Thermotoga maritima	3	0.7274
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7268
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7221
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7209
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7202
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7200
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7168
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7157
Replicase polyprotein 1ab	P0C6X7	R1AB_CVHSA	Human SARS coronavirus	4	0.7140
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7126
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7123
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7116
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7107
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7106
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7103
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7079
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7047
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7046
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7043
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7032
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7031
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7031
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7030
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7023
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7022
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7016
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7011

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