Germacrene-D - Compound Card

Germacrene-D

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Germacrene-D

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C/C/1=C/CCC(=C)/C=C\C(CC1)C(C)C
InChI InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-
InChIKey GAIBLDCXCZKKJE-BZXLUOIMSA-N
Formula C15H24
HBA 0
HBD 0
MW 204.36
Rotatable Bonds 1
TPSA 0.0
LogP 4.89
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 204.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386
2 Cupressus dupreziana Cupressaceae Plantae 329083
3 Cupressus sempervirens Cupressaceae Plantae 13469
4 Cupressus arizonica Cupressaceae Plantae 49011
5 Commiphora quadricincta Burseraceae Plantae 2248429

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]
  • Abderrahim A, Belhamel K, et al. (2010). Chemical composition of the essential oil from Artemisia arborescens L. growing wild in Algeria.. Records of Natural Products,2010,4(1),87-90. [View]
  • 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]
  • 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: 5373727
Nmrshiftdb2: 70005409
CPRiL: 234929
Structure

SMILES: C=C1C=CCCCC=CCC1

Level: 0

Mol. Weight: 204.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.33
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)
0.87
Plasma Protein Binding
47.3
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
9.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.39
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.62
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
3.64
Rat (Acute)
1.6
Rat (Chronic Oral)
1.82
Fathead Minnow
4.27
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
259.84
Hydration Free Energy
0.44
Log(D) at pH=7.4
3.49
Log(P)
6.33
Log S
-5.28
Log(Vapor Pressure)
-1.46
Melting Point
-25.71
pKa Acid
10.98
pKa Basic
8.27
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 0.9218
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9218
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9019
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9019
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8142
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8142
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8018
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8018
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7885
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7885
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7879
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7879
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7864
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7864
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7850
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7850
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7844
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7844
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7801
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7801
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7788
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7788
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7770
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7770
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7767
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7767
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7763
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7763
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7755
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7755
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7749
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7749
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7737
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7737
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7734
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7734
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7682
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7682
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7672
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7672
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7657
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7657
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7647
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7647
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7647
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7647
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7635
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7635
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7633
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7633
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7623
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7623
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7622
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7622
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7621
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7621
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7613
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7613
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7606
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7606
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7571
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7571
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7570
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7570
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7566
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7566
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7559
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7559
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7556
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7556
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7555
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7555
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7531
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7531
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7514
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7514
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7485
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7485
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7475
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7475
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7470
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7470
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7454
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7454
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7444
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7444
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7443
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7443
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7438
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7438
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7435
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7435
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7416
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7416
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7392
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7389
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7389
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7386
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7386
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7373
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7373
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7358
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7358
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7317
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7317
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7302
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7302
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7290
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7274
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7274
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7248
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7248
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7240
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7219
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7219
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7217
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7217
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7191
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7191
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7189
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7189
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7181
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7181
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7179
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7179
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7175
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7175
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7172
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7172
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7107
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7107
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7084
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7031
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7031
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7003
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7003

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