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3'-O-alpha-D-glucopyranosylcalactin
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cardenolide Glycoside
| Canonical Smiles | OCC1O[C@@](O)(O[C@@H]2C[C@@H](C)O[C@@H]3[C@@]2(O)O[C@@H]2C[C@@]4(C=O)[C@H](C[C@H]2O3)CCC2C4CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)[C@H](C([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C35H50O15/c1-16-9-25(50-35(44)29(41)28(40)27(39)24(13-36)49-35)34(43)30(46-16)47-22-11-18-3-4-21-20(32(18,15-37)12-23(22)48-34)5-7-31(2)19(6-8-33(21,31)42)17-10-26(38)45-14-17/h10,15-16,18-25,27-30,36,39-44H,3-9,11-14H2,1-2H3/t16-,18+,19-,20?,21?,22-,23-,24?,25-,27-,28?,29+,30+,31-,32-,33+,34+,35-/m1/s1 |
| InChIKey | GNRNTAGLOVWOQC-XFEKWAQLSA-N |
| Formula | C35H50O15 |
| HBA | 15 |
| HBD | 7 |
| MW | 710.77 |
| Rotatable Bonds | 5 |
| TPSA | 231.13 |
| LogP | -0.86 |
| Number Rings | 8 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 50 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.89 |
| Exact Mass | 710.31 |
| 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
3'-O-alpha-D-glucopyranosylcalactin
- 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:
162817524
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7OC8CCCCO8
Level: 2
Mol. Weight: 710.77 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)C(CCO6)OC7CCCCO7
Level: 1
Mol. Weight: 710.77 g/mol
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7
Level: 1
Mol. Weight: 710.77 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6
Level: 0
Mol. Weight: 710.77 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 710.77 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 710.77 g/mol
Antiproliferative
Na+/k+-atpase inhibitory
Proapoptotic
Absorption
- Caco-2 (logPapp)
- -6.34
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -2.36
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 458.13
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.67
- Plasma Protein Binding
- 62.04
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -1.1
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -10.64
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.74
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.91
- 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
- -830780.99
- Rat (Acute)
- 4.68
- Rat (Chronic Oral)
- 3.63
- Fathead Minnow
- 1056.61
- 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
- 89740.21
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.22
- Log(P)
- -0.98
- Log S
- -2.13
- Log(Vapor Pressure)
- -2892.45
- Melting Point
- 239.06
- pKa Acid
- -0.49
- pKa Basic
- 5.76