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Calactin
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cardenolide Glycoside
| Canonical Smiles | O=C[C@]12C[C@H]3O[C@@]4(O)[C@H](O)C[C@H](O[C@H]4O[C@@H]3C[C@@H]1CCC1C2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C |
|---|---|
| InChI | InChI=1S/C29H40O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-23,25,31,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19?,20?,21-,22-,23-,25+,26-,27-,28+,29+/m1/s1 |
| InChIKey | OWPWFVVPBYFKBG-OCUQDEIGSA-N |
| Formula | C29H40O9 |
| HBA | 9 |
| HBD | 3 |
| MW | 532.63 |
| Rotatable Bonds | 2 |
| TPSA | 131.75 |
| LogP | 2.0 |
| Number Rings | 7 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.86 |
| Exact Mass | 532.27 |
| 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
Calactin
Pecilocerin B
Poekilocerin B
Pekilocerin B
Pokilocerin B
20304-47-6
UNII-6299V7SZXG
6299V7SZXG
HSDB 3467
(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
DTXSID80174192
Card-20(22)-enolide, 3-((4,6-dideoxy-beta-D-erythro-hexopyranos-2-ulos-1-yl)oxy)-2,14-dihydroxy-19-oxo-, (2alpha,3beta,5alpha)-
CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-2,3-(((2S,3S,4R,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))-, (2.ALPHA.,3.BETA.,5.ALPHA.)-
(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo(12.11.0.03,12.05,10.015,23.018,22)pentacosane-14-carbaldehyde
DTXCID6096683
CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-2,3-(((2S,3S,4R,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))-, (2ALPHA,3BETA,5ALPHA)-
CARD-20(22)-ENOLIDE, 3-((4,6-DIDEOXY-BETA-D-ERYTHRO-HEXOPYRANOS-2-ULOS-1-YL)OXY)-2, 14-DIHYDROXY-19-OXO-, (2ALPHA,3BETA,5ALPHA)-
Card20(22)enolide, 3((4,6dideoxybetaDerythrohexopyranos2ulos1yl)oxy)2,14dihydroxy19oxo, (2alpha,3beta,5alpha)
((2s,3s,4r,6r)-2-(((3s,5s,8r,9s,10s,11s,13r,14s,17r)-10-formyl-5,11,14-trihydroxy-13-methyl-12-oxo-17-(6-oxopyran-3-yl)-1,2,3,4,6,7,8,9,11,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-yl)oxy)-3-hydroxy-6-methyl-tetrahydropyran-4-yl) acetate
[(2s,3s,4r,6r)-2-[[(3s,5s,8r,9s,10s,11s,13r,14s,17r)-10-formyl-5,11,14-trihydroxy-13-methyl-12-oxo-17-(6-oxopyran-3-yl)-1,2,3,4,6,7,8,9,11,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3-hydroxy-6-methyl-tetrahydropyran-4-yl] acetate
CHEBI:3299
CHEMBL502127
SCHEMBL24394828
NS00094797
C08854
Q27106014
- 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:
441849
Cas:
20304-47-6
Gnps:
CCMSLIB00005724354
Zinc:
ZINC000008234200
Kegg Ligand:
C08854
Chebi:
3299
Nmrshiftdb2:
70016130
Chembl:
CHEMBL502127
Comptox:
DTXSID80174192
CPRiL:
412902
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7
Level: 1
Mol. Weight: 532.63 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6
Level: 0
Mol. Weight: 532.63 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 532.63 g/mol
Antiproliferative
Na+/k+-atpase inhibitory
Proapoptotic
Absorption
- Caco-2 (logPapp)
- -5.25
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.95
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.25
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.43
- Plasma Protein Binding
- 51.71
- 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
- 2.63
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.26
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.72
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.11
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -2939.77
- Rat (Acute)
- 5.09
- Rat (Chronic Oral)
- 1.77
- Fathead Minnow
- 9.64
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 431.92
- Hydration Free Energy
- -2.87
- Log(D) at pH=7.4
- 2.75
- Log(P)
- 0.9
- Log S
- -3.85
- Log(Vapor Pressure)
- -10.05
- Melting Point
- 250.27
- pKa Acid
- 5.84
- pKa Basic
- 4.6