Germacrene B - Compound Card

Germacrene B

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Germacrene B

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C/C/1=C\CC/C(=C/CC(=C(C)C)CC1)/C
InChI InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+
InChIKey GXEGJTGWYVZSNR-SJRHNVSNSA-N
Formula C15H24
HBA 0
HBD 0
MW 204.36
Rotatable Bonds 0
TPSA 0.0
LogP 5.18
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 1
# Species Family Kingdom NCBI Taxonomy ID
1 Commiphora quadricincta Burseraceae Plantae 2248429

Showing of synonyms

  • 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]
Pubchem: 5281519
Kegg Ligand: C09672
Chebi: 5337
Nmrshiftdb2: 60018915
Metabolights: MTBLC5337

No compound-protein relationship available.

Structure

SMILES: C=C1CC=CCCC=CCC1

Level: 0

Mol. Weight: 204.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.27
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.97
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
34.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
9.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.22
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.43
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
3.82
Rat (Acute)
1.68
Rat (Chronic Oral)
1.73
Fathead Minnow
4.96
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
276.35
Hydration Free Energy
-0.18
Log(D) at pH=7.4
3.21
Log(P)
6.72
Log S
-5.46
Log(Vapor Pressure)
-1.74
Melting Point
8.39
pKa Acid
11.67
pKa Basic
8.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8830
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8830
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8661
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8661
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8135
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8135
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.8077
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.8077
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8007
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8007
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7985
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7985
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7921
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7921
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7901
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7901
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7759
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7759
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
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7743
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7743
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7724
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7724
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7716
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7716
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7714
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7714
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7705
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7705
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7702
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7702
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
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7634
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7634
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7620
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7620
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7609
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7609
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7605
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7605
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7577
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7577
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7535
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7535
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7533
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7533
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7520
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7520
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7508
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7508
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7482
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7482
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7481
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7481
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7477
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7477
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7472
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7472
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7463
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7463
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7459
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7459
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7458
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7458
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7425
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7425
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7425
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7425
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7408
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7408
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7383
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7383
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7382
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7382
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7359
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7359
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7333
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7333
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7332
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7332
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7305
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7305
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7303
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7303
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7301
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7301
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7277
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7277
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7266
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7266
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7265
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7265
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7257
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7257
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7254
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7253
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7253
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7233
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7233
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7232
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7232
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7221
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7221
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7202
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7202
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7180
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7180
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7157
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7157
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7152
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7152
Abscisic acid receptor PYL9 Q5Z8S0 PYL9_ORYSJ Oryza sativa subsp. japonica 3 0.7133
Abscisic acid receptor PYL9 Q5Z8S0 PYL9_ORYSJ Oryza sativa subsp. japonica 3 0.7133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7128
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7128
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7100
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7100
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7070
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7070
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7043
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7043
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7035
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7035
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7016
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7016
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7015
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7015
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7014
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7014
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7006
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7006

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