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Chamazulene
- Family: Plantae - Asteraceae
- Kingdom: Plantae
- Class: Azulene Derivative
| Canonical Smiles | CCc1ccc(c2c(c1)c(C)cc2)C |
|---|---|
| InChI | InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3 |
| InChIKey | GXGJIOMUZAGVEH-UHFFFAOYSA-N |
| Formula | C14H16 |
| HBA | 0 |
| HBD | 0 |
| MW | 184.28 |
| Rotatable Bonds | 1 |
| TPSA | 0.0 |
| LogP | 3.97 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 184.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia arborescens | Asteraceae | Plantae | 72386 |
Showing of synonyms
Chamazulene
Chamazulen
529-05-5
Camazulene
Dimethulene
Dimethulen
1,4-Dimethyl-7-ethylazulene
Azulene, 7-ethyl-1,4-dimethyl-
BA 2784
EINECS 208-449-6
UNII-Z439UH6E5F
BRN 1306577
7-ethyl-1,4-dimethyl-azulene
Z439UH6E5F
AZULENE, 1,4-DIMETHYL-7-ETHYL-
DTXSID70200939
4-05-00-01736 (Beilstein Handbook Reference)
BA-2784
DTXCID50123430
CHAMAZULENE (CONSTITUENT OF CHAMOMILE)
208-449-6
7-Ethyl-1,4-dimethylazulene
CHEBI:3573
Dimethylene
Dimethwlen
Lindazulene
CHAMAZULENE [MI]
CHAMAZULENE [WHO-DD]
CHEMBL495665
1,4-Dimethyl-7-ethyl-Azulene
Chamazulene, analytical standard
GXGJIOMUZAGVEH-UHFFFAOYSA-
MFCD00800984
AKOS040744437
FC74879
LMPR0103410002
DA-72140
FS-10668
HY-121038
NS00013451
C09633
G89287
Q909088
CHAMAZULENE (CONSTITUENT OF CHAMOMILE) [DSC]
InChI=1/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
- 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]
Pubchem:
10719
Cas:
529-05-5
Zinc:
ZINC000000968466
Kegg Ligand:
C09633
Chebi:
3573
Nmrshiftdb2:
20213347
Chembl:
CHEMBL495665
Comptox:
DTXSID70200939
Drugbank:
DB15931
CPRiL:
102019
SMILES: c1ccc(c12)ccccc2
Level: 0
Mol. Weight: 184.28 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.31
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.78
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.94
- Plasma Protein Binding
- 20.53
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-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
- 10.2
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 2.5
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.05
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.48
- 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
- 4.91
- Rat (Acute)
- 1.67
- Rat (Chronic Oral)
- 2.35
- Fathead Minnow
- 3.98
- 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
- 252.58
- Hydration Free Energy
- -1.21
- Log(D) at pH=7.4
- 3.42
- Log(P)
- 5.06
- Log S
- -4.43
- Log(Vapor Pressure)
- -1.26
- Melting Point
- 17.58
- pKa Acid
- 13.38
- pKa Basic
- 5.6
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Albumin | P02769 | ALBU_BOVIN | Bos taurus | 3 | 0.8846 |
| Albumin | P02769 | ALBU_BOVIN | Bos taurus | 3 | 0.8846 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.8835 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.8835 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8823 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8823 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8778 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8778 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8717 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8717 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8634 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8634 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8525 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8525 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8505 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.8505 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8488 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8488 |
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.8380 |
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.8380 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.8295 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.8295 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8166 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8166 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7925 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7925 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7887 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7887 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7879 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7879 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7863 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7863 |
| Chloramphenicol acetyltransferase | P62577 | CAT_ECOLX | Escherichia coli | 2 | 0.7846 |
| Chloramphenicol acetyltransferase | P62577 | CAT_ECOLX | Escherichia coli | 2 | 0.7846 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7771 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7771 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 4 | 0.7769 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 4 | 0.7769 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7753 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7753 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7684 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7684 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7633 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7633 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7618 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7618 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7576 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7576 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7436 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7436 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7412 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7412 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7402 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7402 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7389 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7389 |
| UDP-glycosyltransferase 72B1 | Q9M156 | U72B1_ARATH | Arabidopsis thaliana | 3 | 0.7376 |
| UDP-glycosyltransferase 72B1 | Q9M156 | U72B1_ARATH | Arabidopsis thaliana | 3 | 0.7376 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7371 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7371 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7361 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7361 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7353 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7353 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7345 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7345 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7337 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7337 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7331 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7331 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7310 |
| Alcohol dehydrogenase E chain | P00327 | ADH1E_HORSE | Equus caballus | 3 | 0.7310 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7291 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7291 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7284 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7284 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 3 | 0.7277 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 3 | 0.7277 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7260 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7260 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7229 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7229 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7215 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7215 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7181 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7181 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7116 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7116 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7109 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7109 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7088 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7088 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7069 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7069 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7069 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7069 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7069 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7069 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7039 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7039 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7022 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7022 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7004 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7004 |