Apigenin 7-O-beta-D-(6’’-methylglucuronide) - Compound Card

Apigenin 7-O-beta-D-(6’’-methylglucuronide)

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Apigenin 7-O-beta-D-(6’’-methylglucuronide)

Structure
Zoomed Structure
  • Family: Plantae - Plumbaginaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles COC(=O)C1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C22H20O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-11-6-12(24)16-13(25)8-14(32-15(16)7-11)9-2-4-10(23)5-3-9/h2-8,17-20,22-24,26-28H,1H3/t17?,18-,19-,20?,22+/m0/s1
InChIKey XXKIWCKZQFBXIR-OCNWEEMUSA-N
Formula C22H20O11
HBA 11
HBD 5
MW 460.39
Rotatable Bonds 4
TPSA 176.12
LogP 0.23
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 460.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Limonium duriusculum Plumbaginaceae Plantae 2042423

Showing of synonyms

  • Hamadou M, H, et al. (2021). Apigenin rich-Limonium duriusculum (de Girard) Kuntze promotes apoptosis in HCT116 cancer cells. Natural product research, 2021, 35(17), 2910-2914. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 460.39 g/mol

Structure

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

Level: 1

Mol. Weight: 460.39 g/mol

Structure

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

Level: 1

Mol. Weight: 460.39 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 460.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 460.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 460.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.69
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
-0.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
75.11
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
10.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.070
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.730
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
-120.030
Rat (Acute)
2.290
Rat (Chronic Oral)
3.890
Fathead Minnow
4.290
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
557.610
Hydration Free Energy
-3.510
Log(D) at pH=7.4
1.860
Log(P)
1.22
Log S
-4.69
Log(Vapor Pressure)
-11.1
Melting Point
210.3
pKa Acid
6.61
pKa Basic
3.65
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 0.9497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9261
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9254
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9193
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9178
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9048
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.9005
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8992
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8973
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8972
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8867
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8828
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8808
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8767
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8755
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8705
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8671
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8573
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8545
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8522
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8516
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8475
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8418
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8409
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8394
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8375
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8360
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8335
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8311
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8202
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8175
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8162
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8157
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8156
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8100
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8088
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8082
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8079
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8074
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8054
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8003
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7981
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7980
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7976
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7970
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7966
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7938
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7904
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7888
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7885
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7876
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7868
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7854
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7850
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7798
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7773
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7768
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7739
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7720
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7701
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7679
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7674
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7638
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7629
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7626
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7594
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7582
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7568
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7516
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7515
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7492
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 3 0.7488
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7485
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7468
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7443
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7442
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7442
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7436
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7416
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7412
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7401
Maternal embryonic leucine zipper kinase Q14680 MELK_HUMAN Homo sapiens 4 0.7385
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7382
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7381
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7372
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7346
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7345
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7342
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7337
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7335
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7327
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7326
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7306
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7297
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7278
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7269
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7266
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7266
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7248
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7238
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7236
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7221
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7218
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7209
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7206
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7190
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7183
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7181
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7179
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7174
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7168
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7167
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7166
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7163
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7163
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7162
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7154
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7148
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7143
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7140
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7123
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7120
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7119
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7115
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7112
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7112
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7106
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7079
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7076
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7072
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7067
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7065
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7059
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7054
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7045
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7043
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7025
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7017
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7003

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