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Coroglaucigenin-3-(6-deoxy-beta-D-allopyranoside)-19-acetate
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cardenolide Glycoside
| Canonical Smiles | CC(=O)OC[C@]12CC[C@@H](CC1=CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)O[C@@H]1OC(C)[C@H](C([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C31H44O10/c1-16-25(34)26(35)27(36)28(40-16)41-20-6-10-30(15-39-17(2)32)19(13-20)4-5-23-22(30)7-9-29(3)21(8-11-31(23,29)37)18-12-24(33)38-14-18/h4,12,16,20-23,25-28,34-37H,5-11,13-15H2,1-3H3/t16?,20-,21+,22-,23+,25+,26?,27-,28-,29+,30+,31-/m0/s1 |
| InChIKey | GJKOHPVGPSJEOI-CTAUWDMSSA-N |
| Formula | C31H44O10 |
| HBA | 10 |
| HBD | 4 |
| MW | 576.68 |
| Rotatable Bonds | 5 |
| TPSA | 151.98 |
| LogP | 1.92 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 576.29 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Gomphocarpus sinaicus | Apocynaceae | Plantae | 2291033 |
Showing of synonyms
Coroglaucigenin-3-(6-deoxy-beta-D-allopyranoside)-19-acetate
- El-Askary H, Holzl J, et al. (1995). Cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1995,38(4),943-946. [View]
Pubchem:
162817533
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(=CC4)CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 576.68 g/mol
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 576.68 g/mol
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(=CC4)CCCC5
Level: 1
Mol. Weight: 576.68 g/mol
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 576.68 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 576.68 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 576.68 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.72
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.91
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 3.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.77
- Plasma Protein Binding
- 73.28
- 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
- 2.29
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.18
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.83
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.96
- 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
- -8909.68
- Rat (Acute)
- 3.83
- Rat (Chronic Oral)
- 2.67
- Fathead Minnow
- 23.47
- 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
- 358.91
- Hydration Free Energy
- -2.93
- Log(D) at pH=7.4
- 2.44
- Log(P)
- 0.84
- Log S
- -3.47
- Log(Vapor Pressure)
- -13.6
- Melting Point
- 237.11
- pKa Acid
- 7.79
- pKa Basic
- 6.02
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7803 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7803 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7222 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7222 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7011 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7011 |