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Beta-cubebene
- Family: Plantae - Burseraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | CC([C@@H]1CC[C@H]([C@]23[C@H]1[C@H]2C(=C)CC3)C)C |
|---|---|
| InChI | InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14-,15+/m1/s1 |
| InChIKey | FSRZGYRCMPZNJF-KHMAMNHCSA-N |
| Formula | C15H24 |
| HBA | 0 |
| HBD | 0 |
| MW | 204.36 |
| Rotatable Bonds | 1 |
| TPSA | 0.0 |
| LogP | 4.27 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.87 |
| Exact Mass | 204.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Thymus broussonetii | Lamiaceae | Plantae | 751869 |
| 2 | Cupressus dupreziana | Cupressaceae | Plantae | 329083 |
| 3 | Commiphora quadricincta | Burseraceae | Plantae | 2248429 |
Showing of synonyms
Beta-cubebene
13744-15-5
B-Cubebene
(-)-b-Cubebene
(1R,5S,6R,7S,10R)-10-methyl-4-methylidene-7-propan-2-yltricyclo[4.4.0.01,5]decane
(3as,3br,4s,7r,7ar)-7-methyl-3-methylidene-4-(propan-2-yl)octahydro-1h-cyclopenta[1,3]cyclopropa[1,2]benzene
.beta.-Cubebene
CHEBI:10363
DTXSID201017555
(3aS-(3aalpha,3bbata,4beta,7alpha,7aS*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene
1H-Cyclopenta(1,3)cyclopropa(1,2)benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, (3aS-(3aalpha,3bbata,4beta,7alpha,7aS*))-
(3aS-(3aalpha,3bbata,4b,7a,7aA*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1hcyclopenta(1,3)cyclopropa(1,2)benzene
(3aS-(3aalpha,3bbata,4S,7R,7aS*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1H-cyclopenta(1,3)cyclopropa(1,2)benzene
(1R,5S,6R,7S,10R)-10-methyl-4-methylidene-7-propan-2-yltricyclo(4.4.0.01,5)decane
(3aS,3bR,4S,7R,7aR)-7-methyl-3-methylidene-4-(propan-2-yl)octahydro-1H-cyclopenta(1,3)cyclopropa(1,2)benzene
1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, 2,3,3a.alpha.,3b.alpha.,4,5,6,7-octahydro-4.alpha.-isopropyl-7.beta.-methyl-3-methylene-
1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, (3a.alpha.,3b.alpha.,4.alpha.,7.beta.,7aR*)-
1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3a.alpha.,3b.beta.,4.beta.,7.alpha.,7aS*)]-
DTXCID301475742
(3AS-(3aalpha,3bbata,4b,7a,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene
(3AS-(3aalpha,3bbata,4I2,7I+-,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzene
1H-Cyclopenta(1,3)cyclopropa(1,2)benzene, 2,3,3aalpha,3balpha,4,5,6,7-octahydro-4alpha-isopropyl-7beta-methyl-3-methylene-
1H-Cyclopenta(1,3)cyclopropa(1,2)benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, (3aalpha,3balpha,4alpha,7beta,7aR*)-
1H-Cyclopenta(1,3)cyclopropa(1,2)benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, (3aS-(3aalpha,3bbeta,4beta,7alpha,7aS*))-
Fsrzgyrcmpznjf-mdkblutqsa-n
Fsrzgyrcmpznjf-uhfffaoysa-n
(-)-beta-cubebene
(3aS,3bR,4S,7R,7aR)-4-Isopropyl-7-methyl-3-methyleneoctahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzene
C09648
FSRZGYRCMPZNJF-KHMAMNHCSA-N
HY-N11239A
CS-1098558
NS00121420
Q27108624
- Saad A, Fadli M, et al. (2010). Anticandidal activity of the essential oils of Thymus maroccanus and Thymus broussonetii and their synergism with amphotericin B and fluconazol. Phytomedicine,2010,17(13),1057-1060. [View] [PubMed]
- Assad YOH, Torto B, et al. (1997). Seasonal variation in the essential oil composition of Commiphora quadricincta and its effect on the maturation of immature adults of the desert locust, Schistocerca gregaria. Phytochemistry,1997,44(5),833-841. [View] [PubMed]
- Piovetti L, Francisco C, et al. (1981). Volatile constituents of Cupressus dupreziana and the sesquiterpenes of Cupressus sempervirens. Phytochemistry,1981,20(6),1299-1302. [View]
Pubchem:
93081
Cas:
13744-15-5
Zinc:
ZINC000008234285
Kegg Ligand:
C09648
Chebi:
10363
Nmrshiftdb2:
60019366
Metabolights:
MTBLC10363
No compound-protein relationship available.
SMILES: C1CC(=C)C(C123)C2CCCC3
Level: 0
Mol. Weight: 204.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.55
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.4
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.2
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.32
- Plasma Protein Binding
- 53.6
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.23
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.08
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.36
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.74
- 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
- 2.54
- Rat (Acute)
- 1.5
- Rat (Chronic Oral)
- 1.59
- Fathead Minnow
- 3.92
- 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
- 249.58
- Hydration Free Energy
- 1.05
- Log(D) at pH=7.4
- 4.11
- Log(P)
- 5.52
- Log S
- -5.13
- Log(Vapor Pressure)
- -1.84
- Melting Point
- 56.54
- pKa Acid
- 11.84
- pKa Basic
- 8.87
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.9021 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.9021 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8816 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8816 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.8092 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.8092 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7879 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7879 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7818 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7818 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7731 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7731 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7659 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7659 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7638 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7638 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7619 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7619 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7614 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7614 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7612 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7612 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7508 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7508 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7471 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7471 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7469 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7469 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 2 | 0.7468 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 2 | 0.7468 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7396 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7396 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7334 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7334 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7329 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7329 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7242 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7242 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7183 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7183 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7172 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7172 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7165 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7165 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 2 | 0.7136 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 2 | 0.7136 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7068 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7068 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7035 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7035 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 3 | 0.7015 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 3 | 0.7015 |