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7-O-(beta-D-glucopyranosyl) chrysin

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C23H24O12/c1-31-15-3-9(4-16(32-2)19(15)27)13-7-12(26)18-11(25)5-10(6-14(18)34-13)33-23-22(30)21(29)20(28)17(8-24)35-23/h3-7,17,20-25,27-30H,8H2,1-2H3/t17-,20-,21+,22-,23-/m1/s1
InChIKey	JGXFMIJHKASCIZ-LDBVRRDLSA-N
Formula	C₂₃H₂₄O₁₂
HBA	12
HBD	6
MW	492.43
Rotatable Bonds	6
TPSA	188.51
LogP	0.07
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	492.13
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Calycotome villosa	Leguminosae/Fabaceae	Plantae	52401
2	Rosmarinuseriocalyx	Lamiaceae	Plantae	—

Showing of synonyms

Cherkaoui-Tangi K, Lachkar M, et al. (2008). Pharmacological Studies on Hypotensive, Diuretic and Vasodilator Activities of Chrysin Glucoside from Calycotome villosa in Rats. Phytotherapy research : PTR, 2008, 22(3), 356-61. [View] [PubMed]
Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

Pubchem: 5322022

Cas: 32769-01-0

Zinc: ZINC000031169959

Chebi: 131776

Nmrshiftdb2: 60022726

Metabolights: MTBLC131776

CPRiL: 426175

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 492.43 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 492.43 g/mol

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

Level: 1

Mol. Weight: 492.43 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 492.43 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 492.43 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 492.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.350
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.21

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.960
Plasma Protein Binding: 80.85
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: 11.360
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.990
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.940
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.360
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: -311.980
Rat (Acute): 2.300
Rat (Chronic Oral): 3.860
Fathead Minnow: 4.370
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: 596.840
Hydration Free Energy: -3.440
Log(D) at pH=7.4: 0.800
Log(P): 0.07
Log S: -4.99
Log(Vapor Pressure): -11.43
Melting Point: 213.71
pKa Acid: 6.21
pKa Basic: 4.93

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	0.9777
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9616
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9409
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9284
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9255
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9144
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9079
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.9076
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9071
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9059
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9041
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9015
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8982
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8803
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8676
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8630
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8577
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8570
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8551
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8526
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8483
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8462
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8455
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8439
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8415
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8411
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8368
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8329
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8325
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8320
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8231
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8229
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8225
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8223
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8216
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8146
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8087
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8087
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8055
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8050
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.8000
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7905
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7905
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7902
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7893
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7885
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7883
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7826
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7796
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7783
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7782
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7745
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7742
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7737
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7701
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7686
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7686
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	4	0.7639
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7630
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7625
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7608
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7607
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7583
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7580
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7571
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7565
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7549
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7537
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7527
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7508
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7503
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7497
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7492
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7482
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7471
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7463
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7450
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7450
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7437
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7425
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7412
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7408
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7401
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7392
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7386
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7384
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7379
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7376
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7370
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7357
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7352
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7345
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7345
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7339
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7338
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7326
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7317
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7311
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7303
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7289
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7280
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7278
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7261
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7235
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7232
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7232
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7224
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7221
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7219
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7217
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7208
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7201
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7199
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7189
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7187
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7182
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7161
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7136
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7134
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7130
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7119
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7117
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7110
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7106
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7099
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7099
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7089
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7081
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7078
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7077
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7075
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7074
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7074
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7072
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7071
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7044
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7026
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7025
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7005
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7002

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