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Vulgarin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@@]1([C@@H]2[C@](C)(O)C=CC1=O)C |
|---|---|
| InChI | InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3/t8-,9-,11-,12+,14-,15+/m0/s1 |
| InChIKey | NGPDZEACIWDCKX-WUDKWMPASA-N |
| Formula | C15H20O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 264.32 |
| Rotatable Bonds | 0 |
| TPSA | 63.6 |
| LogP | 1.47 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 264.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia abyssinica | Asteraceae | Plantae | 2869510 |
| 2 | Artemisia judaica | Asteraceae | Plantae | 205369 |
| 3 | Artemisia judaica | Asteraceae | Plantae | 205369 |
| 4 | Achillea fragrantissima | Asteraceae | Plantae | 282738 |
Showing of synonyms
Vulgarin
3162-56-9
Barrelin
Tauremisin
Judaicin (eudesmane naphthofuran)
Judaicin
Tauremizin
TAUREMIZINE
(3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
Judaicin (sesquiterpene)
CHEBI:10024
SMR000445685
(3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione
MLS000728573
MLS001185447
CHEMBL1422618
DTXSID30928884
HMS2225C10
BBL034028
STK013739
AKOS001483019
Vulgarin, >=90% (LC/MS-ELSD)
3a,5,5a,9,9a,9b-Hexahydro-9-hydroxy-3,5a,9-trimethylnaphtho(1,2-b)furan-2,6(3H,4H)-dione
Eudesm-2-en-12-oic acid, 4,6-alpha-dihydroxy-1-oxo-, gamma-lactone, (11S)-
NCGC00247310-01
NCGC00247310-02
NCGC00247310-03
Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S,3aS,5aR,9R,9aS,9bS)-
Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9alpha,9aalpha,9bbeta))-
VS-12384
NS00094007
C09600
Q27108555
(3S,3AS,5AR,9R,9AS,9BS)-9-HYDROXY-3,5A,9-TRIMETHYL-2H,3H,3AH,4H,5H,5AH,6H,9H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2,6-DIONE
9-HYDROXY-3,5A,9-TRIMETHYL-2H,3H,3AH,4H,5H,5AH,6H,9H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2,6-DIONE
- Al-Said MS, Khalifa SI, et al. (1989). Biogenetic-type synthesis of vulgarin and peroxyvulgarin.. Phytochemistry,1989,28(1),107-108. [View]
- Metwally MA, Jakupovic J, et al. (1985). Eudesmanolides from Artemisia judaica.. Phytochemistry,1985,24(5),1103-1104. [View]
- Khafagy SM, El-din AS, et al. (1988). Glaucolide-like sesquiterpene lactones from Artemisia judaica.. Phytochemistry,1988,27(4),1125-1128. [View]
- Ahmed AA, Jakupovk J, et al. (1990). Irregular oxygenated monoterpenes from Achillea fragrantissima.. Phytochemistry,1990,29(4),1322-1324. [View]
Pubchem:
94253
Cas:
3162-56-9
Gnps:
CCMSLIB00000852456
Zinc:
ZINC000003881676
Kegg Ligand:
C09600
Chebi:
10024
Nmrshiftdb2:
60075501
Chembl:
CHEMBL1422618
No compound-protein relationship available.
SMILES: C1C(=O)OC(C12)C3C(CC2)C(=O)C=CC3
Level: 0
Mol. Weight: 264.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.66
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.46
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.94
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.49
- Plasma Protein Binding
- 46.29
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.61
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.08
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.21
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.89
- Micronucleos
- Toxic
- 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
- -2.09
- Rat (Acute)
- 2.41
- Rat (Chronic Oral)
- 1.61
- Fathead Minnow
- 3.7
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 344.35
- Hydration Free Energy
- -7.39
- Log(D) at pH=7.4
- 0.81
- Log(P)
- 0.88
- Log S
- -2.02
- Log(Vapor Pressure)
- -6.04
- Melting Point
- 188.14
- pKa Acid
- 8.68
- pKa Basic
- 5.97
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7190 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7190 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7188 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7188 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7047 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7047 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7023 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7023 |