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Vicenin-2
- Family: Moraceae, Leguminosae, Labiatae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone Glycoside
| Canonical Smiles | OC[C@H]1O[C@H]([C@@H]([C@@H]([C@@H]1O)O)O)c1c(O)c([C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c(c2c1oc(cc2=O)c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17-,18-,21+,22-,23-,24-,26+,27+/m1/s1 |
| InChIKey | FIAAVMJLAGNUKW-JDGZUBLHSA-N |
| Formula | C27H30O15 |
| HBA | 15 |
| HBD | 11 |
| MW | 594.52 |
| Rotatable Bonds | 5 |
| TPSA | 271.2 |
| LogP | -2.39 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 594.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ficus variifolia | Moraceae | Plantae | 425835 |
| 2 | Ficus polita | Moraceae | Plantae | 378027 |
| 3 | Ficus sansibarica | Moraceae | Plantae | 309319 |
| 4 | Ficus saussureana | Moraceae | Plantae | 309296 |
| 5 | Salvia triloba | Labiatae | Plantae | — |
| 6 | Phlomis aurea | Labiatae | Plantae | — |
| 7 | Phlomis floccosa | Labiatae | Plantae | — |
| 8 | Marrubium vulgare | Labiatae | Plantae | — |
| 9 | Stachys aegyptiaca | Labiatae | Plantae | — |
| 10 | Teucrium leucocladum | Labiatae | Plantae | — |
| 11 | Teucrium polium | Labiatae | Plantae | — |
| 12 | Marrubium vulgare | Labiatae | Plantae | — |
| 13 | Adenocarpus anagyrifolius | Leguminosae | Plantae | — |
| 14 | Adenocarpus anagyrifolius var. leiocarpa | Leguminosae | Plantae | — |
| 15 | Adenocarpus artemisifolius | Leguminosae | Plantae | — |
| 16 | Adenocarpus bacquei | Leguminosae | Plantae | — |
| 17 | Adenocarpus boudyi | Leguminosae | Plantae | — |
| 18 | Adenocarpus bracteatus | Leguminosae | Plantae | — |
| 19 | Adenocarpus cincinnatus | Leguminosae | Plantae | — |
| 20 | Adenocarpus complicatus | Leguminosae | Plantae | — |
| 21 | Adenocarpus decorticans | Leguminosae | Plantae | — |
| 22 | Adenocarpus faurei | Leguminosae | Plantae | — |
| 23 | Adenocarpus nainii | Leguminosae | Plantae | — |
| 24 | Adenocarpus telonensis | Leguminosae | Plantae | — |
| 25 | Parkinsonin aculeata | Leguminosae | Plantae | — |
Showing of synonyms
Vicenin-2
23666-13-9
Vicenin II
Vicenin
Vicenin -2
CHEBI:69814
MLS000575019
6,8-di-c-glucosylapigenin
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
5,7,4'-Trihydroxyflavone-6,8-di-C-glucoside
ViceninII
Isovitexin 8-C-beta-glucoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6,8-bis((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
AC1L9D6K
Apigenin-6,8-di-C-glycopyranoside
MFCD08458851
Vicenin 2 (Standard)
SureCN5826175
SCHEMBL5826175
CHEMBL1442950
HY-N2165R
HMS2210F06
HY-N2165
MSK163797
AKOS015896841
FV74184
Vicenin-II
NCGC00247567-01
AC-34904
DA-78880
MS-30565
SMR000232371
1ST163797
CS-0019465
Vicenin 2, primary pharmaceutical reference standard
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one
- Boudjelal A, Henchiri C, et al. (2012). Compositional analysis and in vivo anti-diabetic activity of wild Algerian Marrubium vulgare L. infusion. Fitoterapia,2012,83,286–292. [View] [PubMed]
- Mohamed F. Abdalla, Nabiel A.M. Saleh, et al. (1983). Flavone glycosides of Salvia triloba. Phytochemistry,1983,22(9),2057-2060. [View]
- El-Ansari M, Abdalla M, et al. (1991). Flavonoid constituents of Stachys aegyptiaca. Phytochemistry, 1991,30(4),1169-1173. [View]
- Nawwar M, El-Mousallamy A, et al. (1989). Flavonoid Lactates from Leaves of Marrubium Vulgare. Phytochemistry, 1989, 28(11), 3201-3206.. [View]
- Rafaa S. Essokne, Renée J. Grayer, et al. (2012). Flavonoids as chemosystematic markers for the genus Adenocarpus. Biochemical Systematics and Ecology,2012,42,49–58. [View]
- El-Negoumy S, Abdalla M, et al. (1986). Flavonoids of Phlomis Aurea and P. Floccosa. Phytochemistry, 1986, 25(3), 772-774.. [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]
- Nabil H. El-Sayed, Ahmed A. Ahmed, et al. (1991). Luteolin 7,4'-dimethyl ether 6-C-glucoside from Parkinsonia aculeata. Phytochemistry,1991,30(7),2442. [View]
- S.A. Kawashty, E.M. Gamal El-Din, et al. (1999). The flavonoid chemosystematics of two Teucrium species from Southern Sinai, Egypt. Biochemical Systematics and Ecology,1999,27,657-660. [View]
Pubchem:
442664
Cas:
23666-13-9
Gnps:
CCMSLIB00000077238
Zinc:
ZINC000004098604
Kegg Ligand:
C10195
Chebi:
69814
Nmrshiftdb2:
60022756
Metabolights:
MTBLC69814
Chembl:
CHEMBL1442950
CPRiL:
79656
SMILES: c1ccccc1
Level: 0
Mol. Weight: 78.11 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 222.24 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 146.14 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 86.13 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4
Level: 2
Mol. Weight: 306.36 g/mol
SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3
Level: 1
Mol. Weight: 230.26 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5
Level: 3
Mol. Weight: 390.48 g/mol
SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4
Level: 2
Mol. Weight: 314.38 g/mol
SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 306.36 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3
Level: 1
Mol. Weight: 230.26 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.41
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -6.270
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 9.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.590
- Plasma Protein Binding
- 64.09
- 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
- 6.930
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -4.270
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.770
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.400
- 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
- -9477.270
- Rat (Acute)
- 2.480
- Rat (Chronic Oral)
- 5.020
- Fathead Minnow
- 17.100
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 615.590
- Hydration Free Energy
- -3.140
- Log(D) at pH=7.4
- -1.640
- Log(P)
- -0.42
- Log S
- -3.25
- Log(Vapor Pressure)
- -13.33
- Melting Point
- 207.26
- pKa Acid
- 1.06
- pKa Basic
- 11.43
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8726 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8726 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8495 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8495 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8431 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8431 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8106 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8106 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8101 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8101 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7984 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7984 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7978 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7978 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7911 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7911 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7907 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7907 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 4 | 0.7726 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 4 | 0.7726 |
| Neopullulanase 2 | Q08751 | NEPU2_THEVU | Thermoactinomyces vulgaris | 3 | 0.7665 |
| Neopullulanase 2 | Q08751 | NEPU2_THEVU | Thermoactinomyces vulgaris | 3 | 0.7665 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7551 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7551 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7498 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7498 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7405 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7405 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7389 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7389 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7366 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7366 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7261 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7261 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7238 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7238 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7234 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7234 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7159 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7159 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7035 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7035 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7025 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7025 |