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8-C-beta-D-glucopyranosyl-5,7,4'-trihydroxyflavone
- Family: Plantae - Agavaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1 |
| InChIKey | SGEWCQFRYRRZDC-VPRICQMDSA-N |
| Formula | C21H20O10 |
| HBA | 10 |
| HBD | 7 |
| MW | 432.38 |
| Rotatable Bonds | 3 |
| TPSA | 181.05 |
| LogP | 0.09 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 432.11 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Borago officinalis | Boraginaceae | Plantae | 13363 |
| 2 | Hyphaene thebaica | Arecaceae | Plantae | 115479 |
| 3 | Jatropha multifida | Euphorbiaceae | Plantae | 3996 |
| 4 | Croton zambezicus | Euphorbiaceae | Plantae | 323089 |
| 5 | Moraea sisyrinchium | Iridaceae | Plantae | 148530 |
| 6 | Neurada procumbens | Neuradaceae | Plantae | 32215 |
| 7 | Neurada procumbens | Neuradaceae | Plantae | 32215 |
| 8 | Hyparrhenia hirta | Poaceae | Plantae | 42079 |
| 9 | Cotoneaster orbicularis | Rosaceae | Plantae | 1851000 |
| 10 | Crataegus sinaica | Rosaceae | Plantae | 298646 |
| 11 | Chrysanthemum viscidehirtum | Asteraceae | Plantae | 13422 |
| 12 | Ficus asperifolia | Moraceae | Plantae | 182103 |
| 13 | Ficus polita | Moraceae | Plantae | 378027 |
| 14 | Ficus sansibarica | Moraceae | Plantae | 309319 |
| 15 | Ficus saussureana | Moraceae | Plantae | 309296 |
| 16 | Gnidia involucrata | Thymelaeaceae | Plantae | 142743 |
| 17 | Cordyline fruticosa | Agavaceae | Plantae | 39501 |
Showing of synonyms
8-C-beta-D-glucopyranosyl-5,7,4'-trihydroxyflavone
Vitexin
3681-93-4
Apigenin 8-C-glucoside
Apigenin-8-C-glucoside
8-beta-D-Glucopyranosyl-apigenin
EINECS 222-963-8
UNII-9VP70K75OK
ORIENTOSIDE
VITEXINA
VITEXINE
9VP70K75OK
CHEBI:16954
Flavone, 8-D-glucosyl-4',5,7-trihydroxy-
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-beta-D-glucopyranosyl-2-(4-hydroxyphenyl)-
DTXSID90190287
8C-hexosyl apigenin
VITEXIN (USP-RS)
VITEXIN [USP-RS]
4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
8-glycosylapigenin
(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol
8-glycosyl-apigenin
(1S)-1,5-anhydro-1-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl)-D-glucitol
DTXCID00112778
VITEXIN (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER)
FLAVONE, 8-beta-D-GLUCOPYRANOSYL-4',5,7-TRIHYDROXY-
222-963-8
C21H20O10
MFCD00017456
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
4H-1-Benzopyran-4-one, 8-.beta.-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
Vitexin (Standard)
VITEXIN [WHO-DD]
Vitexin, analytical standard
8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
SCHEMBL25277
CHEMBL487417
HY-N0013R
SGEWCQFRYRRZDC-VPRICQMDSA-N
Apigenin 8-C-.beta.-D-glucoside
HY-N0013
BDBM50362886
HB4123
MSK158047
S9192
AKOS025311479
AC-6086
CCG-208516
MV08032
NCGC00163642-01
Vitexin 100 microg/mL in Acetone:Water
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one
AS-55909
1ST158047
CS-0007090
NS00018314
APIGENIN-8-C-.BETA.-D-GLUCOPYRANOSIDE
C01460
Q259075
Vitexin, primary pharmaceutical reference standard
5,7,4'-Trihydroxyflavone 8-C-.beta.-D-glucopyranoside
Vitexin, United States Pharmacopeia (USP) Reference Standard
FLAVONE, 8-.BETA.-D-GLUCOPYRANOSYL-4',5,7-TRIHYDROXY-
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-.beta.-D-glucopyranosyl-2-(4-hydroxyphenyl)-
8-D-Glucosyl-4',5',7'-trihydroxy-flavone
8-C-b-D-Glucopyranosylapigenin
Oritentoside
- Khallouki F, Hmamouchi M, et al. (2000). A new flavonoid from the aerial parts of Chrysanthemum viscidehirtum. Fitoterapia,2000,71,413-416. [View] [PubMed]
- Shahat AA, Ismail SI, et al. (1998). Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine,1998,5(2),133-136. [View] [PubMed]
- Ferrari J, Terreaux C, et al. (2000). Benzophenone glycosides from Gnidia involucrata. Phytochemistry,2000,54(8),883-889. [View] [PubMed]
- Zemmouri H, Ammar S, et al. (2014). Chemical composition and antioxidant activity of Borago officinalis L. leaf extract growing in Algeria. Arabian Journal of Chemistry,2014,in press. [View]
- Wagner H, Horhammer L, et al. (1970). Flavone-C-glykoside in Croton zambezicus. Phytochemistry,1970,9,897-897. [View]
- Bouaziz M, Simmonds MS, et al. (2001). Flavonoids from Hyparrhenia hirta Stapf (Poaceae) growing in Tunisia. Biochemical Systematics and Ecology,2001,29(8),849-851. [View] [PubMed]
- El-Shabrawy MOA Marzouk MM, Kawashty SA, et al. (2013). Flavonoids from Moraea sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt. International Conference on Applied Life Sciences (ICALS2013),2013,UAE. September 15-17, 2013. [View]
- Marzouk MM, Hussein SR, et al. (2014). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Biochemical Systematics and Ecology,2014,57,67-68. [View]
- Marzouk M, Hussein SR, et al. (2013). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Planta Medica,2013,79-PI46. [View]
- Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]
- Marzouk MS, Moharram FA, et al. (2012). Novel biflavone diglycosides and biological activity of Jatropha multifida leaves. Chemistry of Natural Compounds,2012,48(5),765-770. [View]
- Eldahshan OA, Ayoub NA, et al. (2008). Potential superoxide anion radical scavenging activity of doum palm (Hyphaene thebaica L.) leaves extract. Records of Natural Products,2008,2(3),83-93. [View]
- Fouedjou RT, Teponno RB, et al. (2014). Steroidal saponins from the leaves of Cordyline fruticosa (L.) A. Chev. and their cytotoxic and antimicrobial activity. Phytochemistry Letters, 2014, 7, 62-68. [View]
- El-Mousallamy AM, Hussein SA, et al. (2000). Unusual phenolic glycosides from Cotoneaster orbicularis. Phytochemistry,2000,53(6),699-704. [View] [PubMed]
Pubchem:
5280441
Cas:
3681-93-4
Gnps:
CCMSLIB00005758755
Zinc:
ZINC000004245684
Kegg Ligand:
C01460
Chebi:
16954
Nmrshiftdb2:
60005878
Metabolights:
MTBLC16954
Chembl:
CHEMBL487417
Comptox:
DTXSID90190287
Drugbank:
DB16836
Bindingdb:
50362886
CPRiL:
54730
SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 432.38 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 432.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.5
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.750
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.790
- Plasma Protein Binding
- 82.68
- 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
- 12.380
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.810
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.840
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.280
- 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
- -47.400
- Rat (Acute)
- 2.480
- Rat (Chronic Oral)
- 4.260
- Fathead Minnow
- 3.830
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 622.830
- Hydration Free Energy
- -6.960
- Log(D) at pH=7.4
- 0.460
- Log(P)
- 1.17
- Log S
- -3.81
- Log(Vapor Pressure)
- -12.92
- Melting Point
- 226.28
- pKa Acid
- 4.72
- pKa Basic
- 8.26
| 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 | 0.9359 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9359 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.9274 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.9274 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.9253 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.9253 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.9194 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.9194 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8813 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8813 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8511 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8511 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8473 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8473 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8472 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8472 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 3 | 0.8442 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 3 | 0.8442 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8243 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8243 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.8231 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.8231 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8212 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8212 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8178 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8178 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8156 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8156 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8147 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8147 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8089 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8089 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7807 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7807 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7729 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7729 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7642 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7642 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 4 | 0.7602 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 4 | 0.7602 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7591 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7591 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7552 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7552 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7504 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7504 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7429 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7429 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7409 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7409 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 4 | 0.7390 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 4 | 0.7390 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7339 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7339 |
| Probable nicotinate-nucleotide adenylyltransferase | Q9HX21 | NADD_PSEAE | Pseudomonas aeruginosa | 3 | 0.7328 |
| Probable nicotinate-nucleotide adenylyltransferase | Q9HX21 | NADD_PSEAE | Pseudomonas aeruginosa | 3 | 0.7328 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7225 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7225 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7212 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7212 |
| Tubulin alpha-1B chain | P81947 | TBA1B_BOVIN | Bos taurus | 3 | 0.7201 |
| Tubulin alpha-1B chain | P81947 | TBA1B_BOVIN | Bos taurus | 3 | 0.7201 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7173 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7173 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7081 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7081 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7081 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7081 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7079 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7079 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7070 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7070 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7041 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7041 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 4 | 0.7031 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 4 | 0.7031 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7028 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7028 |