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(+)-onopordopicrin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OC/C/1=C/[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C/C(=C\CC1)/C)OC(=O)C(=C)CO |
|---|---|
| InChI | InChI=1S/C19H24O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,15-17,20-21H,2-4,6-7,9-10H2,1H3/b11-5-,14-8+/t15-,16+,17+/m0/s1 |
| InChIKey | NOZAJYKZMCFNFG-DGKKXOEVSA-N |
| Formula | C19H24O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 348.4 |
| Rotatable Bonds | 4 |
| TPSA | 93.06 |
| LogP | 1.59 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.47 |
| Exact Mass | 348.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea incana | Asteraceae | Plantae | 405077 |
| 2 | Cheirolophus intybaceus | Asteraceae | Plantae | 64995 |
| 3 | Centaurea scoparia | Asteraceae | Plantae | 2072395 |
Showing of synonyms
(+)-onopordopicrin
Onopordopicrin
[(3aR,4S,6Z,10E,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
CHEMBL522604
BDBM50433442
NCGC00169123-01
BRD-K13623064-001-01-0
2-Propenoic acid, 2-(hydroxymethyl)-, 2,3,3a,4,5,8,9,11a-octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4S*,6E,10Z,11aR*))-
- Barrero AF, Oltra JE, et al. (2000). New sources and antifungal activity of sesquiterpene lactones. Fitoterapia,2000,71,60-64. [View] [PubMed]
- Youssef DTA (1998). Sesquiterpene lactones from Centaurea scoparia. Phytochemistry,1998,49(6),1733-1737. [View] [PubMed]
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
CPRiL:
406478
SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2
Level: 0
Mol. Weight: 348.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.66
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.59
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.5
- Plasma Protein Binding
- 45.4
- 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
- 7.89
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.89
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.33
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.4
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -0.61
- Rat (Acute)
- 2.97
- Rat (Chronic Oral)
- 2.29
- Fathead Minnow
- 4.29
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 386.52
- Hydration Free Energy
- -9.18
- Log(D) at pH=7.4
- 1.36
- Log(P)
- 1.36
- Log S
- -3.07
- Log(Vapor Pressure)
- -7.7
- Melting Point
- 135.06
- pKa Acid
- 7.16
- pKa Basic
- 4.59
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8642 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8642 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8507 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8507 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8176 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8176 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8156 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8156 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7251 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7251 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7132 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7132 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 3 | 0.7111 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 3 | 0.7111 |