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Cynaropicrin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OCC(=C)C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=C)[C@H](C2)O |
|---|---|
| InChI | InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1 |
| InChIKey | KHSCYOFDKADJDJ-NQLMQOPMSA-N |
| Formula | C19H22O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 346.38 |
| Rotatable Bonds | 3 |
| TPSA | 93.06 |
| LogP | 1.06 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.47 |
| Exact Mass | 346.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Amberboa tubuliflora | Asteraceae | Plantae | 1284450 |
| 2 | Achillea fragrantissima | Asteraceae | Plantae | 282738 |
| 3 | Cheirolophus sempervirens | Asteraceae | Plantae | 65000 |
| 4 | Cheirolophus mauritanicus | Asteraceae | Plantae | 64998 |
| 5 | Cheirolophus x hortigenus | Asteraceae | Plantae | 41544 |
Showing of synonyms
Cynaropicrin
35730-78-0
Cynaropikrin
2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester
M9233789I9
UNII-M9233789I9
2-Propenoic acid, 2-(hydroxymethyl)-, dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
CHEBI:4038
CHEMBL374146
[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
Cynaropicrin (Standard)
MEGxp0_001095
SCHEMBL1711811
ACon1_000045
HY-N2350R
DTXSID20957143
HY-N2350
BDBM50194430
AKOS032971358
CS-8041
FS-8077
NCGC00168845-01
NCGC00168845-02
DA-52252
XC160151
NS00094008
Cynaropicrin - Cynara cardunculus (artichoke)
C09385
G16186
BRD-K51428447-001-01-5
Q15410905
2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-
8-Hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate
- Ahmed AA, El-Ela MA, et al. (1990). A guaianolide from Amberboa tubuliflora. Phytochemistry,1990,29(12),3946-3947. [View]
- Ahmed AA, Jakupovk J, et al. (1990). Irregular oxygenated monoterpenes from Achillea fragrantissima.. Phytochemistry,1990,29(4),1322-1324. [View]
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem:
119093
Cas:
35730-78-0
Gnps:
CCMSLIB00006525633
Zinc:
ZINC000004098049
Kegg Ligand:
C09385
Chebi:
4038
Nmrshiftdb2:
60032440
Chembl:
CHEMBL374146
Bindingdb:
50194430
CPRiL:
67220
SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C
Level: 0
Mol. Weight: 346.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.56
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.680
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.510
- Plasma Protein Binding
- 53.19
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.000
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.780
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.720
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.030
- 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
- -1.730
- Rat (Acute)
- 3.660
- Rat (Chronic Oral)
- 2.140
- Fathead Minnow
- 3.920
- 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
- 383.210
- Hydration Free Energy
- -8.070
- Log(D) at pH=7.4
- 1.120
- Log(P)
- 0.59
- Log S
- -2.77
- Log(Vapor Pressure)
- -8.43
- Melting Point
- 162.25
- pKa Acid
- 5.95
- pKa Basic
- 3.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8730 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8730 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8338 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8338 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8176 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8176 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7973 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7973 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7902 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7902 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7313 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7313 |
| Ferrichrome outer membrane transporter/phage receptor | P06971 | FHUA_ECOLI | Escherichia coli | 3 | 0.7192 |
| Ferrichrome outer membrane transporter/phage receptor | P06971 | FHUA_ECOLI | Escherichia coli | 3 | 0.7192 |