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Alpha-pinene
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
Canonical Smiles | CC1=CCC2CC1C2(C)C |
---|---|
InChI | InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3 |
InChIKey | GRWFGVWFFZKLTI-UHFFFAOYSA-N |
Formula | C10H16 |
HBA | 0 |
HBD | 0 |
MW | 136.24 |
Rotatable Bonds | 0 |
TPSA | 0.0 |
LogP | 3.0 |
Number Rings | 3 |
Number Aromatic Rings | 0 |
Heavy Atom Count | 10 |
Formal Charge | 0 |
Fraction CSP3 | 0.8 |
Exact Mass | 136.13 |
Number of Lipinski Rule Violations | 0 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Pistacia lentiscus | Anacardiaceae | Plantae | 371726 |
2 | Artemisia herba-alba | Asteraceae | Plantae | 72329 |
3 | Artemisia herba | Asteraceae | Plantae | 268028 |
4 | Artemisia judaica | Asteraceae | Plantae | 205369 |
5 | Thymus broussonetii | Lamiaceae | Plantae | 751869 |
6 | Ammodaucus leucotrichus | Apiaceae | Plantae | 79158 |
7 | Foeniculum vulgare | Apiaceae | Plantae | 2849586 |
8 | Tetraclinis articulata | Cupressaceae | Plantae | 13717 |
9 | Cupressus dupreziana | Cupressaceae | Plantae | 329083 |
10 | Cupressus sempervirens | Cupressaceae | Plantae | 13469 |
11 | Cupressus dupreziana | Cupressaceae | Plantae | 329083 |
12 | Cupressus arizonica | Cupressaceae | Plantae | 49011 |
13 | Chrysanthemum viscidehirtum | Asteraceae | Plantae | 13422 |
14 | Commiphora quadricincta | Burseraceae | Plantae | 2248429 |
15 | Boswellia neglecta | Burseraceae | Plantae | 246345 |
16 | Boswellia species | Burseraceae | Plantae | 173701 |
17 | Anthemis tigrensis | Asteraceae | Plantae | 158234 |
18 | Tarchonanthus camphoratus | Asteraceae | Plantae | 41650 |
19 | Plectranthus marrubioides | Lamiaceae | Plantae | 204214 |
20 | Tetradenia riparia | Lamiaceae | Plantae | 992795 |
Showing of synonyms
Alpha-pinene
2-Pinene
Acintene A
2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
Pin-2(3)-ene
Pinene isomer
2437-95-8
Alfa-Pinene
Sylvapine A
PINENE, ALPHA
NSC 7727
Pin-2-ene
Leavo-95
DTXSID4026501
CHEBI:36740
(+-)-2-pinene
NSC-7727
2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene
PC-500(TERPENE)
FEMA No. 2902
Alpha-Pinene (natural)
FEMA Number 2902
DTXCID006501
4,6,6-Trimethylbicyklo(3,1,1)hept-3-en
2,6,6-Trimethylbicyclo(3.1.1)hept-2-ene
CCRIS 697
PC-500
HSDB 720
DL-Pin-2(3)-ene
EINECS 201-291-9
EINECS 219-445-9
UNII-JPF3YI7O34
BRN 3194807
AI3-24594
Bicyclo(3.1.1)hept-2-ene, 2,6,6-trimethyl
2,6,6-Trimethylbicyclo(3.1.1)-2-heptene
2,6,6-Trimethylbicyclo[3.1.1]-2-heptene
EC 201-291-9
4-05-00-00456 (Beilstein Handbook Reference)
AUSTRALENE
(+-)-alpha-pinene
PINENE (ALPHA)
Alpha-PINENE, (+-)-
Pesticide Code: 067004.
Trimethyl Bicyclo (3.1.1) hept-2-ene
2,6,6-TRIMETHYLBICYCLO (3.1.1)HEPT-2-ENE, 9CL
BICYCLO(3.1.1)HEPT-2-ENE,2,6,6-TRIMETHYL-2-PINENE
201-291-9
80-56-8 2437-95-8
80-56-8
.alpha.-Pinene
(+/-)-2-Pinene
Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-
(+/-)-alpha-Pinene
NSC94522
NSC94523
NCGC00090682-01
(-)-?-Pinene
(1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
CAS-80-56-8
(1S)-(-)-a-Pinene
Alphapinene
Alpha pinene
An alpha-pinene
Cyclic dexadiene
Alpha -pinene
4,6,6-trimethylbicyclo[3.1.1]hept-3-ene
Acitene A
(-)alpha-pinene
A-Pinene PF
Pinene, .alpha.
Alpha [D] Pinene
Alpha [L] Pinene
1R-.alpha.-Pinene
(R)-.alpha.-Pinene
? PINENE
(1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
PINENE, ALPHA (D)
PINENE, ALPHA (L)
(.+/-.)-.alpha.-Pinene
CHEMBL442565
NSC7727
Alpha-Pinene (+/-)-alpha-Pinene
Tox21_110996
Tox21_200108
Tox21_303385
NSC-94522
NSC-94523
PC 500
AKOS000121239
AB86235
AB86464
AB93066
DB15573
UN 2368
NCGC00090682-02
NCGC00257379-01
NCGC00257662-01
FP158530
LS-13835
2,6-Trimethylbicyclo[3.1.1]-2-heptene
DB-017892
Bicyclo[3.1.1]hept-2-ene,6,6-trimethyl-
NS00067073
2,6-Trimethylbicyclo[3.1.1]-2-hept-2-ene
EN300-21685
C09880
Q27104380
Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (.+/-.)-
(+/-)-2-Pinene, 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, alpha-Pinene
- Khallouki F, Hmamouchi MH, et al. (2000). Antibacterial and molluscicidal activities of the essential oil of Chrysanthemum viscidehirtum. Fitoterapia,2000,71,544-546. [View] [PubMed]
- 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]
- Cheraif I, Jannet HB, et al. (2007). Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene. Biochemical Systematics and Ecology,2007,35,813 -820. [View]
- Zoubiri S, Baaliouamer A, et al. (2014). Chemical composition and larvicidal activity of Algerian Foeniculum vulgare seed essential oil. Arabian Journal of Chemistry,2014,7,480-485. [View]
- Amhamdi H, Aouinti F, et al. (2009). Chemical composition of the essential oil of Pistacia lentiscus L. from Eastern Morocco. Records of Natural Products,2009,3(2),90-95. [View]
- Gherraf N, Zellagui A, et al. (2013). Chemical constituents and antimicrobial activity of essential oils of Ammodaucus leucotricus. Arabian Journal of Chemistry, 2013, in press. [View]
- Giordani R, Hadef Y, et al. (2008). Compositions and antifungal activities of essential oils of some Algerian aromatic plants.. Fitoterapia,2008,79,199 -203. [View] [PubMed]
- Belhattab R, Amor L, et al. (2014). Essential oil from Artemisia herba-alba Asso grown wild in Algeria: variability assessment and comparison with an updated literature survey.. Arabian Journal of Chemistry,2014,7,243-251. [View]
- Metwally MA, Jakupovic J, et al. (1985). Eudesmanolides from Artemisia judaica.. Phytochemistry,1985,24(5),1103-1104. [View]
- Zidane A, Tits M, et al. (2014). Phytochemical analysis of Tetraclinis articula in relation to its vasorelaxant property. Journal of Materials and Environmental Sciences,2014,5(5),1368-1375. [View]
- Melese A, Dagne E. (2007). Phytochemical investigation of the resins of Boswellia species collected from Kebtele area in Agew-Awi (Gojjam). M.Sc. Thesis, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]
- Sorsa A, Asfaw N. (2007). Phytochemical investigation on the aerial part of Anthemis tigreensis (chloroform extract). M.Sc. Thesis-3, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]
- Omolo MO, Okinyo D, et al. (2004). Repellency of essential oils of some Kenyan plants against Anopheles gambiae. Phytochemistry,2004,65(20),2797-2802. [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]
- Dekebo A, Dagne E, et al. (2002). Triterpenes from the resin of Boswellia neglecta. Bulletin of the Chemical Society of Ethiopia,2002,16(1),87-90. [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]
- Pauly G, Yani A, et al. (1983). Volatile constituents of the leaves of Cupressus duprezzana and Cupressus semper virens. Phytochemistry,1983,22(4),957-959. [View]
Pubchem:
6654
Cas:
2437-95-8
Gnps:
CCMSLIB00005755834
Kegg Ligand:
C09880
Chebi:
36740
Nmrshiftdb2:
2504
Metabolights:
MTBLC36740
Chembl:
CHEMBL442565
Comptox:
DTXSID4026501
Drugbank:
DB15573
CPRiL:
14787
SMILES: C12CC(C1)CC=C2
Level: 0
Mol. Weight: 136.24 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.42
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.88
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.93
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.58
- Plasma Protein Binding
- 9.78
- 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
- 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
- 12.35
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.54
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.17
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.27
- 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
- 3.15
- Rat (Acute)
- 1.33
- Rat (Chronic Oral)
- 1.45
- Fathead Minnow
- 3.9
- 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
- 162.1
- Hydration Free Energy
- -0.36
- Log(D) at pH=7.4
- 2.36
- Log(P)
- 4.96
- Log S
- -4.35
- Log(Vapor Pressure)
- 0.11
- Melting Point
- -48.19
- pKa Acid
- 12.64
- pKa Basic
- 9.02
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8127 |
Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8127 |
Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7997 |
Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7997 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7990 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7990 |
Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7898 |
Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7898 |
Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7778 |
Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7778 |
Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7762 |
Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7762 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7754 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7754 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7754 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7754 |
Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7739 |
Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7739 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7716 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7716 |
Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7667 |
Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7667 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7631 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7631 |
Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7590 |
Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7590 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7574 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7574 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7503 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7503 |
Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7463 |
Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7463 |
Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7392 |
Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7392 |
Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7358 |
Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7358 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7356 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7356 |
17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7339 |
17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7339 |
Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7327 |
Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7327 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7215 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7215 |
Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7214 |
Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7214 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7210 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7210 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7209 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7209 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7205 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7205 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7202 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7202 |