Alpha-pinene - Compound Card

Alpha-pinene

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Alpha-pinene

Structure
Zoomed Structure
  • 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

  • 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
Kegg Ligand: C09880
Chebi: 36740
Nmrshiftdb2: 2504
Metabolights: MTBLC36740
Drugbank: DB15573
CPRiL: 14787
Structure

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

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