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Apigenin-8-C-alpha-L-rhamnopyranosyl-(1→2)-O-beta-D-glucopyranoside
- Family: Plantae - Caryophyllaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone C-Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)O)O)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16-,19-,20+,21+,22+,23-,25-,26+,27-/m1/s1 |
| InChIKey | LYGPBZVKGHHTIE-HWPNFVCTSA-N |
| Formula | C27H30O14 |
| HBA | 14 |
| HBD | 9 |
| MW | 578.52 |
| Rotatable Bonds | 5 |
| TPSA | 239.97 |
| LogP | -1.06 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 578.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vaccaria pyramidata | Caryophyllaceae | Plantae | 39387 |
Showing of synonyms
Apigenin-8-C-alpha-L-rhamnopyranosyl-(1→2)-O-beta-D-glucopyranoside
- Said R, Hamed A, et al. (2019). Flavone C-glycosides from Vaccaria pyramidata: Structure elucidation by spectroscopy and theoretical calculations. Phytochemistry Letters, 2019, 29, 119-124. [View]
No compound-protein relationship available.
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)C4C(CCCO4)OC5CCCCO5
Level: 3
Mol. Weight: 578.52 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C3C(CCCO3)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 578.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.4
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.730
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 4.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.760
- Plasma Protein Binding
- 69.3
- 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
- 9.190
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.230
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.800
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.620
- 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
- -5816.140
- Rat (Acute)
- 2.460
- Rat (Chronic Oral)
- 4.100
- Fathead Minnow
- 13.380
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 548.300
- Hydration Free Energy
- -2.950
- Log(D) at pH=7.4
- -0.190
- Log(P)
- 0.41
- Log S
- -4.16
- Log(Vapor Pressure)
- -11.28
- Melting Point
- 173.59
- pKa Acid
- 4.82
- pKa Basic
- 8.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8927 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8635 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8578 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8278 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7930 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7508 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7459 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7300 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7095 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7033 |