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1beta,5beta-dihydroxyeudesm-4(15)-en-6beta,11betaH-12,6-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C1O[C@H]2[C@H]([C@@H]1C)CC[C@@]1([C@@]2(O)C(=C)CC[C@H]1O)C |
|---|---|
| InChI | InChI=1S/C15H22O4/c1-8-4-5-11(16)14(3)7-6-10-9(2)13(17)19-12(10)15(8,14)18/h9-12,16,18H,1,4-7H2,2-3H3/t9-,10-,11+,12-,14-,15+/m0/s1 |
| InChIKey | CJLHTKGWEUGORV-UVGOUCATSA-N |
| Formula | C15H22O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 266.34 |
| Rotatable Bonds | 0 |
| TPSA | 66.76 |
| LogP | 1.41 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 266.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia hugueti | Asteraceae | Plantae | 4219 |
Showing of synonyms
1beta,5beta-dihydroxyeudesm-4(15)-en-6beta,11betaH-12,6-olide
Isogallicadiol
(-)-Isogallicadiol
129138-11-0
(3S,3aS,5aS,6R,9aS,9bS)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one
(3S,3aS,5aS,6R,9aS,9bS)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-3,3a,4,5,6,7,8,9b-octahydrobenzo(g)(1)benzofuran-2-one
DTXSID70926304
6,9a-dihydroxy-3,5a-dimethyl-9-methylidenedecahydronaphtho[1,2-b]furan-2(3H)-one
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
No compound-protein relationship available.
SMILES: C=C1CCCC(CC2)C1C(C23)OC(=O)C3
Level: 0
Mol. Weight: 266.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.48
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.46
- Plasma Protein Binding
- 43.91
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 7.06
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.6
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.51
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 3.73
- 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
- -1.19
- Rat (Acute)
- 2.91
- Rat (Chronic Oral)
- 1.56
- Fathead Minnow
- 3.78
- 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
- 339.95
- Hydration Free Energy
- -8.37
- Log(D) at pH=7.4
- 0.48
- Log(P)
- 1.43
- Log S
- -2.1
- Log(Vapor Pressure)
- -6.85
- Melting Point
- 171.98
- pKa Acid
- 8.58
- pKa Basic
- 6.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8447 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8447 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8247 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8247 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7858 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7858 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7726 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7726 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7598 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7598 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7553 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7553 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7324 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7324 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7006 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7006 |