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Apigenin-7-O-beta-D-glucuronopyranoside methyl ester

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

Canonical Smiles	COC(=O)C1OC(c2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)C(C(C1O)O)O
InChI	InChI=1S/C22H20O10/c1-30-22(29)21-19(28)17(26)18(27)20(32-21)10-6-12(24)16-13(25)8-14(31-15(16)7-10)9-2-4-11(23)5-3-9/h2-8,17-21,23-24,26-28H,1H3
InChIKey	XYSMYQHUNIXDEF-UHFFFAOYSA-N
Formula	C₂₂H₂₀O₁₀
HBA	10
HBD	5
MW	444.39
Rotatable Bonds	3
TPSA	166.89
LogP	0.57
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	444.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Salvia barrelieri	Lamiaceae	Plantae	2886697

Showing of synonyms

Lehbili M, Alabdul Magid A, et al. (2018). Antibacterial, antioxidant and cytotoxic activities of triterpenes and flavonoids from the aerial parts of Salvia barrelieri Etl.. Natural product research, 2018, 32(22), 2683-2691. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1c(cc2)cc(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 444.39 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)C3CCCCO3

Level: 1

Mol. Weight: 444.39 g/mol

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

Level: 1

Mol. Weight: 444.39 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 444.39 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 444.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 444.39 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: -5.000
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.080
Plasma Protein Binding: 22.4
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: 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: 9.860
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.300
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.050
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.170
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: -72.780
Rat (Acute): 2.410
Rat (Chronic Oral): 3.890
Fathead Minnow: 4.220
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 554.620
Hydration Free Energy: -4.050
Log(D) at pH=7.4: 1.830
Log(P): 1.49
Log S: -4.49
Log(Vapor Pressure): -10.54
Melting Point: 208.62
pKa Acid: 6.56
pKa Basic: 4.72

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9496
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9252
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9234
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9033
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8926
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8784
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8711
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8696
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8628
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8609
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8608
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8495
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8426
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8409
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8404
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8329
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8320
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8282
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8270
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8253
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.8177
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8102
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8080
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8053
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8039
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7996
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7968
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7950
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7939
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7840
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7809
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7798
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7781
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7751
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7743
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7734
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7722
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7713
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7681
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7677
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7562
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7524
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7502
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7489
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7486
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7472
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7469
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7429
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7414
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	2	0.7390
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7389
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7386
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7373
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7328
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7317
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7310
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7308
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7295
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7292
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7291
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7290
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7290
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7227
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7218
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7214
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7211
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7203
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7189
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7169
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	3	0.7154
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7147
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7145
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7141
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7140
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7140
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7139
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7137
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7132
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7121
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7109
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7109
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7103
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7103
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7099
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7065
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7063
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7043
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7026
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7004

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