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2''-O-galloylisovitexin

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

Canonical Smiles	Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(c(c2O)[C@@H]1OC(COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H](C1O)O)O)O
InChI	InChI=1S/C28H24O14/c29-12-3-1-10(2-4-12)17-7-13(30)20-18(41-17)8-14(31)21(24(20)36)27-26(38)25(37)23(35)19(42-27)9-40-28(39)11-5-15(32)22(34)16(33)6-11/h1-8,19,23,25-27,29,31-38H,9H2/t19?,23-,25+,26?,27+/m1/s1
InChIKey	VHHCLIKWPGQXHO-ZRJKONDKSA-N
Formula	C₂₈H₂₄O₁₄
HBA	14
HBD	9
MW	584.49
Rotatable Bonds	5
TPSA	247.81
LogP	1.07
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	584.12
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]

Pubchem: 44257729

Chebi: 188108

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)c(c3)ccc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 584.49 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)c(c3)ccc(c34)occc4=O

Level: 2

Mol. Weight: 584.49 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 584.49 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 584.49 g/mol

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

Level: 1

Mol. Weight: 584.49 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 584.49 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 584.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 584.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 584.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.480
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.770
Plasma Protein Binding: 63.0
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: 11.910
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.620
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.040
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.690
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: -9054.970
Rat (Acute): 2.490
Rat (Chronic Oral): 4.280
Fathead Minnow: 20.730
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 574.770
Hydration Free Energy: -3.170
Log(D) at pH=7.4: 0.930
Log(P): 1.94
Log S: -5.45
Log(Vapor Pressure): -11.77
Melting Point: 254.44
pKa Acid: 5.29
pKa Basic: 8.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9550
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9496
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9227
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9149
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9091
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9065
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8989
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8986
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8977
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8921
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.8836
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8786
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8753
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8744
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8735
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8711
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8704
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8525
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8521
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8485
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8474
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.8466
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8435
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8360
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8350
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8304
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8191
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8189
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8189
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8102
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8094
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8090
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8080
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8067
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8061
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8040
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8007
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7990
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7989
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7924
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7923
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7864
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7839
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7827
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7787
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7771
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7703
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7656
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7632
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.7632
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7628
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7617
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7615
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7588
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7527
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7438
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7435
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7401
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7394
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7393
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7391
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7382
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7380
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7370
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7366
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7363
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7362
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7347
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7337
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7326
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7298
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7283
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7268
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7262
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7237
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7237
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7232
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7231
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7225
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7225
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7223
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7214
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7206
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7196
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7195
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7188
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7159
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7139
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7127
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7124
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7107
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7103
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7074
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7074
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7073
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7069
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7064
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7051
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	5	0.7049
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7047
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7001

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