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Deacylcynaropicrin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O[C@H]1C[C@@H]2[C@H](C1=C)C1OC(=O)C(=C)[C@@H]1[C@H](CC2=C)O |
|---|---|
| InChI | InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h9-14,16-17H,1-5H2/t9-,10-,11-,12-,13+,14?/m0/s1 |
| InChIKey | VPRPYNVJJXOFKZ-RTHOXKBDSA-N |
| Formula | C15H18O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 262.3 |
| Rotatable Bonds | 0 |
| TPSA | 66.76 |
| LogP | 0.96 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 262.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cheirolophus uliginosus | Asteraceae | Plantae | 65003 |
| 2 | Cheirolophus mauritanicus | Asteraceae | Plantae | 64998 |
| 3 | Cheirolophus x hortigenus | Asteraceae | Plantae | 41544 |
Showing of synonyms
Deacylcynaropicrin
31565-50-1
(3aR,4S,6aR,8S,9aR)-4,8-dihydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Azuleno(4,5-b)furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
(3aR,4S,6aR,8S,9aR)-4,8-Dihydroxy-3,6,9-trimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one
DTXSID40185461
- 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:
116653
SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C
Level: 0
Mol. Weight: 262.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.36
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.49
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.47
- Plasma Protein Binding
- 42.73
- 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
- 7.51
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.41
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.6
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.9
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- 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
- 0.52
- Rat (Acute)
- 3.57
- Rat (Chronic Oral)
- 1.89
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 340.34
- Hydration Free Energy
- -9.21
- Log(D) at pH=7.4
- 0.58
- Log(P)
- 0.72
- Log S
- -1.96
- Log(Vapor Pressure)
- -6.85
- Melting Point
- 168.55
- pKa Acid
- 6.87
- pKa Basic
- 4.74
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9282 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9282 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.9033 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.9033 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8998 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8998 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7853 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7853 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7519 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7519 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7205 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7205 |