Gamma-terpinene - Compound Card

Gamma-terpinene

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Gamma-terpinene

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles CC1=CCC(=CC1)C(C)C
InChI InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3
InChIKey YKFLAYDHMOASIY-UHFFFAOYSA-N
Formula C10H16
HBA 0
HBD 0
MW 136.24
Rotatable Bonds 1
TPSA 0.0
LogP 3.31
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 10
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 136.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329
2 Thymus broussonetii Lamiaceae Plantae 751869
3 Daucus glaber Apiaceae Plantae 4038
4 Coriandrum sativum Apiaceae Plantae 4047
5 Cupressus dupreziana Cupressaceae Plantae 329083
6 Cupressus sempervirens Cupressaceae Plantae 13469
7 Cupressus dupreziana Cupressaceae Plantae 329083
8 Cupressus arizonica Cupressaceae Plantae 49011
9 Chrysanthemum viscidehirtum Asteraceae Plantae 13422
10 Commiphora quadricincta Burseraceae Plantae 2248429
11 Plectranthus marrubioides Lamiaceae Plantae 204214

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]
  • Sriti J, Bettaieb I, et al. (2014). Chemical composition and antioxidant activity of the coriander cake obtained by extrusion. Arabian Journal of Chemistry,2014, in press. [View]
  • 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]
  • Mansour ESS, Maatooq GT, et al. (2004). Essential oil of Daucus glaber Forssk. Zeitschrift für Naturforschung C,2004,59,373-378. [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]
  • 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: 7461
Kegg Ligand: C09900
Chebi: 10577
Nmrshiftdb2: 10008721
Metabolights: MTBLC10577
Pdb Ligand: 9NI
CPRiL: 20619
Structure

SMILES: C1=CCC=CC1

Level: 0

Mol. Weight: 136.24 g/mol

Antibacterial
Antimicrobial
Molluscicidal

Absorption

Caco-2 (logPapp)
-4.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
10.51
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
Non-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
9.56
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.37
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
0.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.05
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
3.17
Rat (Acute)
1.57
Rat (Chronic Oral)
1.77
Fathead Minnow
4.07
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
177.64
Hydration Free Energy
0.4
Log(D) at pH=7.4
2.21
Log(P)
4.46
Log S
-4.13
Log(Vapor Pressure)
0.03
Melting Point
-21.38
pKa Acid
10.66
pKa Basic
8.75
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 0.9181
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9181
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8596
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8596
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8196
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8196
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8062
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8062
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7934
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7934
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7898
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7898
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7877
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7877
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7814
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7814
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7788
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7788
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7747
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7747
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7737
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7737
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7727
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7727
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7689
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7689
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7687
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7687
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7683
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7683
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7654
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7654
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7632
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7632
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7618
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7618
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7610
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7610
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7606
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7606
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7605
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7605
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7604
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7604
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7596
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7596
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7589
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7589
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7584
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7584
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7577
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7577
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7574
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7574
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7542
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7538
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7529
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7529
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7517
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7517
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7510
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7510
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7506
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7506
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7506
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7506
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7478
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7478
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7473
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7473
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7470
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7470
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7436
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7436
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7418
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7418
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7397
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7397
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7383
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7383
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7381
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7381
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7372
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7372
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7368
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7368
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7366
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7366
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7365
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7365
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7361
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7361
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7349
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7349
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7316
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7316
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7305
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7305
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7283
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7266
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7203
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7203
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7150
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7150
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7141
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7141
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7139
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7139
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7107
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7107
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7095
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7095
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7061
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7061
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7054
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7054
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7048
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7048
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7039
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7039
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7014
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7014
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7006
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7006

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