Select a section from the left sidebar
Taccalonolide A
- Family: Plantae - Dioscoreaceae
- Kingdom: Plantae
- Class: Terpenoid
| Canonical Smiles | CC(=O)O[C@H]1[C@H]2[C@@H]([C@@H](O)C(=O)[C@@H]3[C@]2(C)[C@@H](OC(=O)C)[C@H]2O[C@H]2C3)[C@H]2[C@@]([C@H]1OC(=O)C)(C)[C@H]1[C@H](C)C=C3[C@]([C@@H]1[C@@H]2OC(=O)C)(C)[C@](C)(O)C(=O)O3 |
|---|---|
| InChI | InChI=1S/C36H46O14/c1-12-10-19-35(8,36(9,44)32(43)50-19)24-21(12)34(7)22(28(24)45-13(2)37)20-23(29(46-14(3)38)31(34)48-16(5)40)33(6)17(25(41)26(20)42)11-18-27(49-18)30(33)47-15(4)39/h10,12,17-18,20-24,26-31,42,44H,11H2,1-9H3/t12-,17-,18+,20+,21+,22-,23-,24+,26-,27+,28-,29+,30+,31+,33+,34-,35+,36-/m1/s1 |
| InChIKey | PTTJLTMUKRRHAT-VJAKQJMOSA-N |
| Formula | C36H46O14 |
| HBA | 14 |
| HBD | 2 |
| MW | 702.75 |
| Rotatable Bonds | 4 |
| TPSA | 201.56 |
| LogP | 1.41 |
| Number Rings | 7 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 50 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 702.29 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tacca leontopetaloides | Dioscoreaceae | Plantae | 72648 |
Showing of synonyms
Taccalonolide A
108885-68-3
AC1L9BGV
CHEMBL1821838
[(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14,25-triacetyloxy-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-13-yl] acetate
((1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14,25-triacetyloxy-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo(13.10.0.02,12.05,11.07,9.016,24.019,23)pentacos-18-en-13-yl) acetate
(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-Tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo(13.10.0.0,.0,.0,.0,.0,)pentacos-18-en-10-yl acetic acid
(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-Tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.0,.0,.0,.0,.0,]pentacos-18-en-10-yl acetic acid
(2R,3R,5S)-2-(1-hydroxy-1-methyl-ethyl)-5-[(3R,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]tetrahydropyran-3-ol
(2R,3R,5S)-2-(1-hydroxy-1-methyl-ethyl)-5-((3R,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-17-yl)tetrahydropyran-3-ol
CHEBI:9388
C08635
DTXSID80910895
PTTJLTMUKRRHAT-VJAKQJMOSA-N
HY-N2416
IEA88568
AKOS037515195
DA-78159
MS-31170
CS-0022618
Q27108373
5,7-Dihydroxy-1,5,5a,11a,13a-pentamethyl-4,8-dioxo-4,5,5a,5b,6,6a,6b,7,8,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-icosahydro-1H-oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-6,11,12,13-tetrayl tetraacetate
- Abdel-Aziz AME (1988). Molluscicidal activity of the Sudanese plant Tacca leontopetaloides. PhD Thesis, University of Wales Institute of Science and Technology (UWIST), 1988. [View]
Pubchem:
441685
Cas:
108885-68-3
Gnps:
CCMSLIB00006424913
Zinc:
ZINC000095616643
Kegg Ligand:
C08635
Chebi:
9388
Nmrshiftdb2:
60078119
Metabolights:
MTBLC9388
Chembl:
CHEMBL1821838
CPRiL:
77082
SMILES: C12C(O2)CC3C(C1)C(=O)CC4C5C(CCC34)C6C(C5)C7C(=CC6)OC(=O)C7
Level: 0
Mol. Weight: 702.75 g/mol
Clinical potential for cancer treatment
Absorption
- Caco-2 (logPapp)
- -5.29
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.6
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 197.61
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.16
- Plasma Protein Binding
- 68.17
- 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
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 7.49
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.16
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.75
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.89
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -363054.79
- Rat (Acute)
- 5.45
- Rat (Chronic Oral)
- 2.39
- Fathead Minnow
- 470.12
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 35844.67
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.42
- Log(P)
- 1.15
- Log S
- -4.84
- Log(Vapor Pressure)
- -1171.92
- Melting Point
- 256.88
- pKa Acid
- 2.91
- pKa Basic
- 0.32
No predicted protein targets found for this compound.