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19-acetylglucofrugoside
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cardenolide Glycoside
| Canonical Smiles | OCC1O[C@@](O)(O[C@H]2CC[C@]3([C@H](C2)CC=C2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)COC(=O)C)[C@H](C([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C31H44O12/c1-16(33)41-15-29-9-5-19(42-31(39)27(37)26(36)25(35)23(13-32)43-31)12-18(29)3-4-22-21(29)6-8-28(2)20(7-10-30(22,28)38)17-11-24(34)40-14-17/h4,11,18-21,23,25-27,32,35-39H,3,5-10,12-15H2,1-2H3/t18-,19-,20+,21-,23?,25+,26?,27-,28+,29+,30-,31-/m0/s1 |
| InChIKey | ZYRPJCLYYOJFPF-LCAZPICKSA-N |
| Formula | C31H44O12 |
| HBA | 12 |
| HBD | 6 |
| MW | 608.68 |
| Rotatable Bonds | 6 |
| TPSA | 192.44 |
| LogP | 0.21 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 608.28 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Gomphocarpus sinaicus | Apocynaceae | Plantae | 2291033 |
Showing of synonyms
19-acetylglucofrugoside
- Abdel-Azim NS, Hammouda FM, et al. (1996). Re-investigation of the cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1996,42(2),523-529. [View]
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 608.68 g/mol
SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 608.68 g/mol
SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CCCC5
Level: 1
Mol. Weight: 608.68 g/mol
SMILES: C1CCC(C12)CCC3C2=CCC4C3CCCC4
Level: 0
Mol. Weight: 608.68 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 608.68 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 608.68 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.45
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.06
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 10.76
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.86
- Plasma Protein Binding
- 76.13
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 0.98
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.55
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.8
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.82
- 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
- -20478.14
- Rat (Acute)
- 3.65
- Rat (Chronic Oral)
- 3.35
- Fathead Minnow
- 41.11
- 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
- 344.58
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.64
- Log(P)
- -1.05
- Log S
- -2.34
- Log(Vapor Pressure)
- -13.95
- Melting Point
- 224.77
- pKa Acid
- 4.96
- pKa Basic
- 7.62
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9001 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9001 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8755 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8755 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8261 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8261 |