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12-dehydroxyghalakinoside
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cardenolide Glycoside
| Canonical Smiles | OC[C@@H]1C[C@@H](O)[C@]2([C@@H](O1)O[C@H]1[C@H](O2)C[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)CO)O |
|---|---|
| InChI | InChI=1S/C29H42O10/c1-26-6-4-19-20(28(26,34)7-5-18(26)15-8-24(33)36-13-15)3-2-16-9-21-22(11-27(16,19)14-31)39-29(35)23(32)10-17(12-30)37-25(29)38-21/h8,16-23,25,30-32,34-35H,2-7,9-14H2,1H3/t16-,17-,18+,19-,20+,21+,22+,23+,25-,26+,27+,28-,29-/m0/s1 |
| InChIKey | HIFCBBCVEWARQA-KQERWQABSA-N |
| Formula | C29H42O10 |
| HBA | 10 |
| HBD | 5 |
| MW | 550.65 |
| Rotatable Bonds | 3 |
| TPSA | 155.14 |
| LogP | 0.77 |
| Number Rings | 7 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 550.28 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pergularia tomentosa | Apocynaceae | Plantae | 264979 |
| 2 | Pergularia tomentosa | Apocynaceae | Plantae | 264979 |
Showing of synonyms
12-dehydroxyghalakinoside
3-[(1S,3R,5S,7S,9R,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-19-yl]-2H-furan-5-one
3-((1S,3R,5S,7S,9R,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo(12.11.0.03,12.05,10.015,23.018,22)pentacosan-19-yl)-2H-furan-5-one
912539-81-2
CHEMBL447312
- Hamed AI, Plaza A, et al. (2006). Cardenolide glycosides from Pergularia tomentosa and their proapoptotic activity in Kaposi’s Sarcoma cells. Journal of Natural Products,2006,69(9),1319-1322. [View] [PubMed]
- Piacente S, Masullo M, et al. (2009). Cardenolides from Pergularia tomentosa display cytotoxic activity resulting from their potent inhibition of Na+/K+-ATPase. Journal of Natural Products,2009,72(2),1087-1091. [View] [PubMed]
Pubchem:
16086567
Cas:
912539-81-2
Zinc:
ZINC000044281636
Nmrshiftdb2:
70036647
Chembl:
CHEMBL447312
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7
Level: 1
Mol. Weight: 550.65 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6
Level: 0
Mol. Weight: 550.65 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 550.65 g/mol
Antiproliferative
Na+/k+-atpase inhibitory
Proapoptotic
Absorption
- Caco-2 (logPapp)
- -5.94
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.040
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1.39
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.620
- Plasma Protein Binding
- 67.86
- 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
- 1.150
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.970
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -3.110
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.250
- 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
- -5087.880
- Rat (Acute)
- 3.910
- Rat (Chronic Oral)
- 2.660
- Fathead Minnow
- 13.700
- 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
- 422.250
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.270
- Log(P)
- 0.1
- Log S
- -2.64
- Log(Vapor Pressure)
- -10.23
- Melting Point
- 227.72
- pKa Acid
- 6.57
- pKa Basic
- 6.72
| 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 | 0.8767 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8767 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7093 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7093 |