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Jaeschkeanadiol p-hydroxybenzoate
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | CC1=CC[C@@]2([C@@H]([C@H](C1)OC(=O)c1ccc(cc1)O)[C@](CC2)(O)C(C)C)C |
|---|---|
| InChI | InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1 |
| InChIKey | CYSHNJQMYORNJI-YUVXSKOASA-N |
| Formula | C22H30O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 358.48 |
| Rotatable Bonds | 3 |
| TPSA | 66.76 |
| LogP | 4.46 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 358.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ferula sinaica | Apiaceae | Plantae | 1514050 |
| 2 | Ferula hermonis | Apiaceae | Plantae | 662815 |
| 3 | Ferula hermonis | Apiaceae | Plantae | 662815 |
Showing of synonyms
Jaeschkeanadiol p-hydroxybenzoate
Ferutinin
Ferutinine
41743-44-6
4-Oxy-6-(4-oxybezoyloxy)dauc-8,9-en
[(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate
Benzoic acid, 4-hydroxy-, (3R,3aS,4S,8aR)-1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester
Benzoic acid, 4-hydroxy-, 1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester, (3R-(3alpha,3abeta,4beta,8aalpha))-
((3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl) 4-hydroxybenzoate
110-651-3
Tefestrol
From Ferula tingiatana
4mg7
Jaeschkeanadiol salicylate
CHEMBL465040
Ferutinin, >=98% (HPLC)
SCHEMBL12512403
DTXSID20961947
CHEBI:230617
Jaeschkeanadiol p-hydroxy benzoate
3-Hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate
BDBM50539730
NSC606959
NSC-606959
DA-73340
HY-125703
CS-0093377
G91055
AJ-738/21233008
Q27452770
(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate
[(3S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate
- Geroushi A, Auzi AA, et al. (2011). Antiinflammatory sesquiterpenes from the root oil of Ferula hermonis. Phytotherapy Research,2011,25,774-777. [View] [PubMed]
- Ibraheim ZZ, Abdel-Mageed WM, et al. (2012). Antimicrobial antioxidant daucane sesquiterpenes from Ferula hermonis Boiss. Phytotherapy Research,2012,26,579-586. [View] [PubMed]
- Ahmed AA (1990). New Sesquiterpenes from Ferula sinaica. Journal of Natural Products,1990,53(2),483-486. [View] [PubMed]
Pubchem:
354654
Cas:
41743-44-6
Zinc:
ZINC000002564854
Chembl:
CHEMBL465040
Pdb Ligand:
27H
Bindingdb:
50539730
CPRiL:
58070
SMILES: c1ccccc1C(=O)OC2CC=CCC(C23)CCC3
Level: 1
Mol. Weight: 358.48 g/mol
SMILES: C1CCC(C12)CCC=CC2
Level: 0
Mol. Weight: 358.48 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 358.48 g/mol
Anti-inflammatory
Antibacterial
Radical scavenging
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.5
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.69
- Plasma Protein Binding
- 79.17
- 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
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- 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
- 8.8
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.72
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.0
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.28
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -1.53
- Rat (Acute)
- 2.5
- Rat (Chronic Oral)
- 2.06
- Fathead Minnow
- 3.98
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 388.55
- Hydration Free Energy
- -7.12
- Log(D) at pH=7.4
- 4.2
- Log(P)
- 5.42
- Log S
- -5.08
- Log(Vapor Pressure)
- -6.75
- Melting Point
- 170.07
- pKa Acid
- 7.76
- pKa Basic
- 5.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7436 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7436 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7149 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7149 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7026 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7026 |