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Pungiolide A
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(=O)/C=C/C1=CCC2C(CC1C)OC(=O)C12OC2CC3C(CC(C2(C=C1C(=O)C)O)C)OC(=O)C3=C |
|---|---|
| InChI | InChI=1S/C29H34O8/c1-14-10-24-21(9-8-19(14)7-6-16(3)30)29(27(33)36-24)22(18(5)31)13-28(34)15(2)11-23-20(12-25(28)37-29)17(4)26(32)35-23/h6-8,13-15,20-21,23-25,34H,4,9-12H2,1-3,5H3/b7-6+ |
| InChIKey | BGZGKGJBTWDZQU-VOTSOKGWSA-N |
| Formula | C29H34O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 510.58 |
| Rotatable Bonds | 3 |
| TPSA | 116.2 |
| LogP | 2.94 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 510.23 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Xanthium pungens | Asteraceae | Plantae | 1979456 |
Showing of synonyms
Pungiolide A
NSC644193
3'-acetyl-4'a-hydroxy-5',7-dimethyl-9'-methylene-6-[(E)-3-oxobut-1-enyl]spiro[4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-3,2'-5,6,6a,9a,10,10a-hexahydrofuro[[?]:[?]]cyclohepta[[?]]pyran]-2,8'-dione
Spiro[2H-cyclohepta[b]furan-3(4H),6'(2'H)-furo[2',3':5,6]cyclohepta[1,2-b]pyran]-2,2'-dione, 7'-acetyl-3',3a,3'a,4',4'a,7,8,8a,8'a,9',10',10'a-dodecahydro-8'a-hydroxy-7,9'-dimethyl-3'-methylene-6-[(1E)-3-oxo-1-butenyl]-
- Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem:
5918884
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(CC2)C1CC(O3)C2C=CC34C5C(OC4=O)CCC=CC5
Level: 0
Mol. Weight: 510.58 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.65
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.73
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.81
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.95
- Plasma Protein Binding
- 47.92
- 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
- Non-Inhibitor
Excretion
- Clearance
- 10.97
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.69
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.3
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.68
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -736.51
- Rat (Acute)
- 3.23
- Rat (Chronic Oral)
- 2.17
- Fathead Minnow
- 5.93
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 462.76
- Hydration Free Energy
- -2.9
- Log(D) at pH=7.4
- 2.8
- Log(P)
- 1.09
- Log S
- -5.06
- Log(Vapor Pressure)
- -8.45
- Melting Point
- 188.3
- pKa Acid
- 6.62
- pKa Basic
- 2.75
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9260 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9260 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8765 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8765 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8559 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8559 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8453 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8453 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7819 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7819 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7079 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7079 |