Apigenin-7-O-beta-D-glucuronopyranoside - Compound Card

Apigenin-7-O-beta-D-glucuronopyranoside

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Apigenin-7-O-beta-D-glucuronopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Salicaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles OC(=O)C1OC(Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)C(C(C1O)O)O
InChI InChI=1S/C21H18O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)
InChIKey JBFOLLJCGUCDQP-UHFFFAOYSA-N
Formula C21H18O11
HBA 10
HBD 6
MW 446.36
Rotatable Bonds 4
TPSA 187.12
LogP 0.14
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 446.08
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Oncoba spinosa Salicaceae Plantae 179733

Showing of synonyms

  • Djouossi MG, Tamokou JD, et al. (2015). Antimicrobial and antioxidant flavonoids from the leaves of Oncoba spinosa Forssk. (Salicaceae).. BMC complementary and alternative medicine,2015, 15, 134. [View] [PubMed]
Pubchem: 5387370
Chebi: 182306
Nmrshiftdb2: 70128151
CPRiL: 412932
Structure

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

Level: 2

Mol. Weight: 446.36 g/mol

Structure

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

Level: 1

Mol. Weight: 446.36 g/mol

Structure

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

Level: 1

Mol. Weight: 446.36 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 446.36 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 446.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 446.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.89
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.33
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.15
Plasma Protein Binding
34.53
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
7.87
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.03
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
-67.01
Rat (Acute)
2.18
Rat (Chronic Oral)
4.11
Fathead Minnow
4.36
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
587.63
Hydration Free Energy
-4.62
Log(D) at pH=7.4
-0.72
Log(P)
1.02
Log S
-4.11
Log(Vapor Pressure)
-11.95
Melting Point
221.95
pKa Acid
4.93
pKa Basic
5.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9544
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9491
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9316
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9254
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9187
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9072
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.9010
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9002
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8891
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8768
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8767
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8716
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8647
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8548
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8539
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8454
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8448
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8441
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8426
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8405
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8376
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.8372
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8332
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8320
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8313
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8282
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8267
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8239
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8194
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8168
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 3 0.8159
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8139
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8095
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8094
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.8084
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8080
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8004
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8000
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7999
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7997
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7977
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7939
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7913
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7896
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7881
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7873
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7864
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7832
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.7830
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7784
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7762
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.7732
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7719
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7718
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7701
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7699
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7686
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7685
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7678
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7636
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7617
Mitogen-activated protein kinase kinase kinase 21 Q5TCX8 M3K21_HUMAN Homo sapiens 3 0.7608
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7590
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7587
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7574
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7573
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 3 0.7539
Nonspecific lipid-transfer protein, putative C9ZUV7 C9ZUV7_TRYB9 Trypanosoma brucei gambiense 3 0.7526
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7523
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7522
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7514
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7507
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7484
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7475
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7475
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7458
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7451
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7431
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7417
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7387
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7379
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 3 0.7365
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7358
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7348
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7343
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7335
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7316
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7308
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7304
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7285
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7276
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7258
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7248
Chemotaxis protein CheA Q56310 CHEA_THEMA Thermotoga maritima 3 0.7246
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7221
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7207
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7193
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7193
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7178
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7167
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7167
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7160
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7155
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7155
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7153
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7152
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7143
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7143
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7135
Metabotropic glutamate receptor 7 Q14831 GRM7_HUMAN Homo sapiens 3 0.7110
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7108
Arginine kinase O15992 KARG_ANTJA Anthopleura japonica 3 0.7097
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7086
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7068
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7057
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7045
Sensor protein PhoQ P23837 PHOQ_ECOLI Escherichia coli 3 0.7043
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7042
Phosphoglycerate kinase 1 P00558 PGK1_HUMAN Homo sapiens 3 0.7033
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7026
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7024
6-phosphogluconate dehydrogenase, decarboxylating P96789 6PGD_LACLM Lactococcus lactis subsp. cremoris 3 0.7020
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7017
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7015
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7014
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7011

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