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Frugoside
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cardenolide Glycoside
| Canonical Smiles | OC[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)OC1O[C@H](C)[C@H]([C@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C29H44O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,15,17-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t15-,17-,18+,19-,20+,21-,23-,24-,25-,26?,27-,28-,29+/m1/s1 |
| InChIKey | WPVGSIBYLZQSIK-VEZJFPMXSA-N |
| Formula | C29H44O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 536.66 |
| Rotatable Bonds | 4 |
| TPSA | 145.91 |
| LogP | 1.43 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 536.3 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Gomphocarpus sinaicus | Apocynaceae | Plantae | 2291033 |
Showing of synonyms
Frugoside
546-02-1
3-[(3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-10-(hydroxymethyl)-13-methyl-3-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
56324-39-1
DTXSID70276235
3-((3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-10-(hydroxymethyl)-13-methyl-3-((3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-one
DTXCID50227563
Cannogenol-3-O-beta-D-allomethyloside
Frugosid [German]
Frugosid
Coroglaucigenin-D-allomethylosid [German]
Coroglaucigenin-D-allomethylosid
Card-20(22)-enolide, 3-((6-deoxy-D-allopyranosyl)oxy)-14,19-dihydroxy-, (3-beta,5-alpha)-
Card-20(22)-enolide, 3-((6-deoxy-D-allopyranosyl)oxy)-14,19-dihydroxy-, (3beta,5alpha)-
NS00094781
- Abdel-Azim NS, Hammouda FM, et al. (1996). Re-investigation of the cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1996,42(2),523-529. [View]
CPRiL:
116228
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 536.66 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 536.66 g/mol
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5
Level: 1
Mol. Weight: 536.66 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4
Level: 0
Mol. Weight: 536.66 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 536.66 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 536.66 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.9
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.11
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.75
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.66
- Plasma Protein Binding
- 72.39
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 0.37
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.97
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -2.9
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.92
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Toxic
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -2470.29
- Rat (Acute)
- 3.73
- Rat (Chronic Oral)
- 2.81
- Fathead Minnow
- 6.13
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 488.12
- Hydration Free Energy
- -2.96
- Log(D) at pH=7.4
- 2.21
- Log(P)
- 0.31
- Log S
- -2.94
- Log(Vapor Pressure)
- -11.35
- Melting Point
- 225.54
- pKa Acid
- 7.34
- pKa Basic
- 6.97