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Ghalakinoside
- 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)CCC1C2C[C@@H](O)[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)CO)O |
|---|---|
| InChI | InChI=1S/C29H42O11/c1-26-17(14-6-24(34)37-12-14)4-5-28(26,35)18-3-2-15-7-20-21(10-27(15,13-31)19(18)9-22(26)32)40-29(36)23(33)8-16(11-30)38-25(29)39-20/h6,15-23,25,30-33,35-36H,2-5,7-13H2,1H3/t15-,16-,17+,18?,19?,20+,21+,22+,23+,25-,26-,27+,28-,29-/m0/s1 |
| InChIKey | NPHHLSOQKLWOCK-WUASNRRDSA-N |
| Formula | C29H42O11 |
| HBA | 11 |
| HBD | 6 |
| MW | 566.64 |
| Rotatable Bonds | 3 |
| TPSA | 175.37 |
| LogP | -0.26 |
| Number Rings | 7 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 566.27 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pergularia tomentosa | Apocynaceae | Plantae | 264979 |
| 2 | Pergularia tomentosa | Apocynaceae | Plantae | 264979 |
Showing of synonyms
Ghalakinoside
119459-76-6
3-[(1S,3S,5S,6S,8S,10S,14R,15S,17R,18S,19R,23R)-5,6,17,22-Tetrahydroxy-8,14-bis(hydroxymethyl)-18-methyl-4,9,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-19-yl]-2H-furan-5-one
Card-20(22)-enolide, 12,14,19-trihydroxy-2,3-((tetrahydro-3,4-dihydroxy-6-(hydroxymethyl)-2H-pyran-3,2-diyl)bis(oxy))-, (3beta(2S,3S,4S,6S),5alpha,12beta)-
DTXSID80922973
4-[3a,7a,8,15-Tetrahydroxy-10,13a-bis(hydroxymethyl)-15a-methylicosahydro-1H,8H-cyclopenta[7,8]phenanthro[2,3-b]pyrano[2,3-e][1,4]dioxin-1-yl]furan-2(5H)-one
- 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]
CPRiL:
77408
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7
Level: 1
Mol. Weight: 566.64 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6
Level: 0
Mol. Weight: 566.64 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 566.64 g/mol
Antiproliferative
Na+/k+-atpase inhibitory
Proapoptotic
Absorption
- Caco-2 (logPapp)
- -6.21
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.150
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2.68
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.610
- Plasma Protein Binding
- 62.2
- 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
- 0.380
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.280
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -2.550
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.070
- 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
- -7592.930
- Rat (Acute)
- 4.240
- Rat (Chronic Oral)
- 2.940
- Fathead Minnow
- 18.760
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 381.400
- Hydration Free Energy
- -2.930
- Log(D) at pH=7.4
- 1.480
- Log(P)
- -0.99
- Log S
- -2.09
- Log(Vapor Pressure)
- -10.8
- Melting Point
- 213.9
- pKa Acid
- 5.65
- pKa Basic
- 6.27
| 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 | 0.9116 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9116 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8750 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8750 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8572 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8572 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7688 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7688 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7662 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7662 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7456 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7456 |