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Cuparene
- Family: Plantae - Cupressaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | Cc1ccc(cc1)[C@]1(C)CCCC1(C)C |
|---|---|
| InChI | InChI=1S/C15H22/c1-12-6-8-13(9-7-12)15(4)11-5-10-14(15,2)3/h6-9H,5,10-11H2,1-4H3/t15-/m0/s1 |
| InChIKey | SLKPBCXNFNIJSV-HNNXBMFYSA-N |
| Formula | C15H22 |
| HBA | 0 |
| HBD | 0 |
| MW | 202.34 |
| Rotatable Bonds | 1 |
| TPSA | 0.0 |
| LogP | 4.46 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 202.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cupressus dupreziana | Cupressaceae | Plantae | 329083 |
Showing of synonyms
Cuparene
(+)-Cuparene
(R)-Cuparene
(R)-1-Methyl-4-(1,2,2-trimethylcyclopentyl)benzene
1-methyl-4-[(1R)-1,2,2-trimethylcyclopentyl]benzene
Cuparene, (+)-
UNII-24IR5X2B93
(R)-(+)-p-(1,2,2-Trimethylcyclopentyl)toluene
24IR5X2B93
EINECS 241-061-5
Benzene, 1-methyl-4-(1,2,2-trimethylcyclopentyl)-, (R)-
DTXSID70168762
Benzene, 1-methyl-4-(1,2,2-trimethylcyclopentyl)-, (theta)-
BENZENE, 1-METHYL-4-(1,2,2-TRIMETHYLCYCLOPENTYL)-, (.THETA.)-
1-methyl-4-((1R)-1,2,2-trimethylcyclopentyl)benzene
(1R,6S)-3-((1S,3S)-3-bromo-1,2,2-trimethylcyclopentyl)-6-chloro-6-methylcyclohex-3-en-1-ol
(1R,6S)-3-[(1S,3S)-3-bromo-1,2,2-trimethylcyclopentyl]-6-chloro-6-methylcyclohex-3-en-1-ol
DTXCID2091253
Slkpbcxnfnijsv-hnnxbmfysa-n
Slkpbcxnfnijsv-oahllokosa-n
16982-00-6
Toluene, p-(1,2,2-trimethylcyclopentyl)-, (R)-(+)-
56324-31-3
MFCD00043118
1-Methyl-4-(1,2,2-trimethylcyclopentyl)benzene #
(R)-1-(p-Tolyl)-1,2,2-trimethylcyclopentane
CHEBI:167407
HY-N9626
AKOS015914036
LMPR0103140001
SB46933
TS-10159
NS00021037
(+)-Cuparene, >=99.0% (sum of enantiomers, GC)
Q27253858
- 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:
86895
Cas:
16982-00-6
Zinc:
ZINC000059778361
Chebi:
167407
Nmrshiftdb2:
60019674
Comptox:
DTXSID70168762
No compound-protein relationship available.
SMILES: C1CCCC1c2ccccc2
Level: 1
Mol. Weight: 202.34 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 202.34 g/mol
SMILES: C1CCCC1
Level: 0
Mol. Weight: 202.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.34
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.12
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.08
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.3
- Plasma Protein Binding
- 63.2
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-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
- 8.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 3.44
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.35
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.58
- 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
- 2.41
- Rat (Acute)
- 1.74
- Rat (Chronic Oral)
- 1.62
- Fathead Minnow
- 4.12
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 262.56
- Hydration Free Energy
- -1.09
- Log(D) at pH=7.4
- 4.02
- Log(P)
- 5.64
- Log S
- -5.73
- Log(Vapor Pressure)
- -1.86
- Melting Point
- 69.71
- pKa Acid
- 13.18
- pKa Basic
- 9.71
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.8804 |
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.8804 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8472 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8472 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8130 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8130 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7962 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7962 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7891 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7891 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7738 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7738 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7737 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7737 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7713 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7713 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7648 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7648 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7634 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7634 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7612 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7612 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 2 | 0.7514 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 2 | 0.7514 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7481 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7481 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7406 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7406 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 2 | 0.7405 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 2 | 0.7405 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7391 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7391 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7376 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7376 |
| Choline kinase alpha | P35790 | CHKA_HUMAN | Homo sapiens | 3 | 0.7291 |
| Choline kinase alpha | P35790 | CHKA_HUMAN | Homo sapiens | 3 | 0.7291 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7277 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7277 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7236 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7236 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7215 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7215 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7205 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7205 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7201 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7201 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7194 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7194 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7191 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7191 |
| Glutathione S-transferase A1 | P08263 | GSTA1_HUMAN | Homo sapiens | 2 | 0.7190 |
| Glutathione S-transferase A1 | P08263 | GSTA1_HUMAN | Homo sapiens | 2 | 0.7190 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7186 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7186 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7150 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7150 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7140 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7140 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 2 | 0.7119 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 2 | 0.7119 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7085 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7085 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7060 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7060 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7054 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7054 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7053 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7053 |
| Thiosulfate reductase | Q72LA4 | Q72LA4_THET2 | Thermus thermophilus | 3 | 0.7052 |
| Thiosulfate reductase | Q72LA4 | Q72LA4_THET2 | Thermus thermophilus | 3 | 0.7052 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7036 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7036 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7031 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7031 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7028 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7028 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7006 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7006 |