Beta-phellandrene - Compound Card

Beta-phellandrene

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Beta-phellandrene

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles CC(C1CCC(=C)C=C1)C
InChI InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3
InChIKey LFJQCDVYDGGFCH-UHFFFAOYSA-N
Formula C10H16
HBA 0
HBD 0
MW 136.24
Rotatable Bonds 1
TPSA 0.0
LogP 3.16
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 Petroselinum crispum Apiaceae Plantae 4043
2 Foeniculum vulgare Apiaceae Plantae 2849586
3 Cupressus dupreziana Cupressaceae Plantae 329083
4 Cupressus dupreziana Cupressaceae Plantae 329083
5 Cupressus sempervirens Cupressaceae Plantae 13469
6 Cupressus sempervirens Cupressaceae Plantae 13469
7 Cupressus arizonica Cupressaceae Plantae 49011
8 Chrysanthemum macrocarpum Asteraceae Plantae 13422

Showing of synonyms

  • 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]
  • Boutaghane N, Kabouche A, et al. (2008). Composition of the essential oil of Chrysanthemum macrocarpum from Algeria. Chemistry of Natural Compounds,2008,44(6),817-818. [View]
  • MacLeod AJ, Snyder CH, et al. (1985). Volatile aroma constituents of parsley leaves. Phytochemistry,1985,24(11),2623-2627. [View]
  • 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: 11142
Chebi: 48741
Nmrshiftdb2: 60019097
Metabolights: MTBLC48741
CPRiL: 30581
Structure

SMILES: C=C1C=CCCC1

Level: 0

Mol. Weight: 136.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.24
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.84
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)
0.52
Plasma Protein Binding
11.94
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
10.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.51
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
0.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.7
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
3.66
Rat (Acute)
1.56
Rat (Chronic Oral)
1.89
Fathead Minnow
3.87
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
167.95
Hydration Free Energy
0.51
Log(D) at pH=7.4
2.28
Log(P)
4.2
Log S
-3.93
Log(Vapor Pressure)
0.22
Melting Point
-49.96
pKa Acid
11.35
pKa Basic
8.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8569
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8569
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8256
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8256
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7996
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7996
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7962
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7962
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7923
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7923
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7921
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7921
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7920
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7920
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7909
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7909
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7901
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7901
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7887
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7887
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7877
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7877
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7871
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7871
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7866
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7866
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7849
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7849
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7847
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7847
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7840
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7840
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7817
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7817
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7816
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7816
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7805
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7805
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7802
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7802
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7798
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7798
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7789
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7789
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7779
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7779
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7766
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7766
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7760
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7760
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7756
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7756
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7753
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7753
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7751
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7751
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7744
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7744
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7739
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7716
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7716
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7702
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7702
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7701
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7701
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7699
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7699
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7686
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7686
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7680
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7680
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7678
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7678
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7657
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7657
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7655
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7655
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7652
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7652
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7644
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7644
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7642
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7642
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7641
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7641
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7618
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7618
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7606
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7606
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7590
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7590
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7579
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7579
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7560
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7560
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7559
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7557
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7557
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7539
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7539
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7539
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7539
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7533
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7533
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7491
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7491
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7471
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7471
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7455
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7455
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7450
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7450
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7427
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7427
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7417
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7417
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7412
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7412
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7391
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7391
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7387
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7387
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7363
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7363
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7353
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7353
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7347
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7347
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7323
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7323
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7307
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7307
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7259
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7259
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7216
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7216
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7177
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7177
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7122
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7068
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7068
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7066
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7066
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7005
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7005

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