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Apigenin 7-diglucuronide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone Glycoside
| Canonical Smiles | OC(=O)[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C27H26O17/c28-9-3-1-8(2-4-9)13-7-12(30)15-11(29)5-10(6-14(15)41-13)40-27-23(19(34)18(33)22(43-27)25(38)39)44-26-20(35)16(31)17(32)21(42-26)24(36)37/h1-7,16-23,26-29,31-35H,(H,36,37)(H,38,39)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1 |
| InChIKey | SJFTVAAHLRFBST-DBFWEQBMSA-N |
| Formula | C27H26O17 |
| HBA | 15 |
| HBD | 9 |
| MW | 622.49 |
| Rotatable Bonds | 7 |
| TPSA | 283.34 |
| LogP | -1.94 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.37 |
| Exact Mass | 622.12 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia judaica | Asteraceae | Plantae | 205369 |
Showing of synonyms
Apigenin 7-diglucuronide
Clerodendrin
119738-57-7
(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
DTXSID10152569
Apigenin-7-O-glucuronopyranosyl(1-2)-glucuronopyranoside
Beta-D-Glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-
Apigenin-7-O-glucuronopyranosyl(1--2)-glucuronopyranoside
(2S,3S,4S,5R,6R)-6-((2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-(5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxyoxan-3-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
DTXCID1075060
C27H26O17
HY-N2426
AKOS040751215
DA-72271
MS-30796
CS-0022639
E87166
- Saleh NAM, El-Negoumy SI, et al. (1987). Flavonoids of Artemisia judaica, A. monosperma and A. Herba-alba.. Phytochemistry,1987,26(11),3059-3064. [View]
Pubchem:
5488004
Cas:
119738-57-7
Zinc:
ZINC000095909566
Nmrshiftdb2:
60073360
Comptox:
DTXSID10152569
No compound-protein relationship available.
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5
Level: 3
Mol. Weight: 622.49 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4
Level: 2
Mol. Weight: 622.49 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 622.49 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 622.49 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 622.49 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 622.49 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 622.49 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 622.49 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 622.49 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.65
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.35
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 10.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.06
- Plasma Protein Binding
- 84.92
- 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
- Inhibitor
Excretion
- Clearance
- 0.77
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.11
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.52
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.45
- 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
- -20769.81
- Rat (Acute)
- 2.16
- Rat (Chronic Oral)
- 3.85
- Fathead Minnow
- 40.85
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 502.38
- Hydration Free Energy
- -3.11
- Log(D) at pH=7.4
- -2.12
- Log(P)
- -0.4
- Log S
- -3.83
- Log(Vapor Pressure)
- -18.3
- Melting Point
- 201.9
- pKa Acid
- 2.99
- pKa Basic
- 6.76
| 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 | 0.9486 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9486 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.8928 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.8928 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8831 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8831 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8830 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8830 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.8729 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.8729 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8714 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8714 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8653 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8653 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8527 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8527 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8444 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8444 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8354 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8354 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8351 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8351 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8107 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8107 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.8101 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.8101 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8067 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8067 |
| ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 3 | 0.8007 |
| ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 3 | 0.8007 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7993 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7993 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7984 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7984 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7874 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7874 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7814 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7814 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7768 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7768 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 3 | 0.7726 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 3 | 0.7726 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7705 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7705 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.7610 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.7610 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.7604 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.7604 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7530 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7530 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7527 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7527 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 4 | 0.7517 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 4 | 0.7517 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7502 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7502 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7467 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7467 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7432 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7432 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7400 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7400 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7308 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7308 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7285 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7285 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7279 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7279 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.7240 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.7240 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7221 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7221 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7204 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7204 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7196 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7196 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7184 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7184 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 4 | 0.7169 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 4 | 0.7169 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7166 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7166 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7158 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7158 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7124 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7124 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7075 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7075 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7051 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7051 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7046 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7046 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7040 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7040 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.7020 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 3 | 0.7020 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.7020 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 3 | 0.7020 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7017 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7017 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7016 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7016 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7009 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7009 |