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Isoshyobunone
- Family: Plantae - Piperaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | C=C[C@]1(C)CC[C@H](C(=O)C1=C(C)C)C(C)C |
|---|---|
| InChI | InChI=1S/C15H24O/c1-7-15(6)9-8-12(10(2)3)14(16)13(15)11(4)5/h7,10,12H,1,8-9H2,2-6H3/t12-,15+/m0/s1 |
| InChIKey | YMIHAYABXZORPU-SWLSCSKDSA-N |
| Formula | C15H24O |
| HBA | 1 |
| HBD | 0 |
| MW | 220.36 |
| Rotatable Bonds | 2 |
| TPSA | 17.07 |
| LogP | 4.15 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 220.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Piper capense | Piperaceae | Plantae | 247681 |
Showing of synonyms
Isoshyobunone
(-)-Isoshyobunone
CHEBI:68150
(3S,6S)-3-ethenyl-3-methyl-6-propan-2-yl-2-propan-2-ylidenecyclohexan-1-one
21698-46-4
CHEMBL1814554
YMIHAYABXZORPU-SWLSCSKDSA-N
DTXSID001317632
Q27136640
P-Menthan-3-one, 2-isopropylidene-1-vinyl-, (1S,4S)-
(3S,6S)-6-Isopropyl-3-methyl-2-(propan-2-ylidene)-3-vinylcyclohexanone
Cyclohexanone, 3-ethenyl-3-methyl-6-(1-methylethyl)-2-(1-methylethylidene)-, (3S,6S)-
Cyclohexanone, 3-ethenyl-3-methyl-6-(1-methylethyl)-2-(1-methylethylidene)-, (3S-trans)-
- Debebe E, Dessalegn T, et al. (2018). Chemical constituents and antioxidant activities of the fruits extracts of Piper capense. Bull. Chem. Soc. Ethiop. 2018, 32(1), 167-174. [View]
Pubchem:
5318673
Cas:
21698-46-4
Zinc:
ZINC000095536915
Chebi:
68150
Nmrshiftdb2:
60033040
Metabolights:
MTBLC68150
Chembl:
CHEMBL1814554
No compound-protein relationship available.
SMILES: C=C1C(=O)CCCC1
Level: 0
Mol. Weight: 220.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.32
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.27
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.68
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.61
- Plasma Protein Binding
- 66.63
- 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
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- 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
- 10.9
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.85
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.29
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.57
- 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
- 1.22
- Rat (Acute)
- 1.78
- Rat (Chronic Oral)
- 1.66
- Fathead Minnow
- 4.21
- 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
- 268.67
- Hydration Free Energy
- -2.84
- Log(D) at pH=7.4
- 3.87
- Log(P)
- 5.05
- Log S
- -4.19
- Log(Vapor Pressure)
- -1.79
- Melting Point
- 19.69
- pKa Acid
- 10.08
- pKa Basic
- 5.8
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8787 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8728 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7915 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7747 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7687 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7622 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7535 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7452 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7439 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7429 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7407 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7396 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7395 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7393 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7378 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7362 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7361 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7343 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7337 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7306 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7282 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7249 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7144 |
| Bile acid receptor | Q62735 | NR1H4_RAT | Rattus norvegicus | 4 | 0.7135 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7117 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7036 |