Nerolidol
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Basic Info
| Common Name | Nerolidol(F05622) |
| 2D Structure | |
| Description | Nerolidol is found in bitter gourd. Nerolidol is a component of many essential oils. The (S)-enantiomer is the commoner and occurs mostly as the (S)-(E)-isomer. Nerolidol is a flavouring agent. Nerolidol has been shown to exhibit anti-fungal function (A7933). Nerolidol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units. |
| FRCD ID | F05622 |
| CAS Number | 7212-44-4 |
| PubChem CID | 5284507 |
| Formula | C15H26O |
| IUPAC Name | (6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol |
| InChI Key | FQTLCLSUCSAZDY-SDNWHVSQSA-N |
| InChI | InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+ |
| Canonical SMILES | CC(=CCCC(=CCCC(C)(C=C)O)C)C |
| Isomeric SMILES | CC(=CCC/C(=C/CCC(C)(C=C)O)/C)C |
| Wikipedia | Nerolidol |
| Synonyms |
(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
NEROLIDOL
trans-Nerolidol
40716-66-3
7212-44-4
Nerolidol (natural)
FCI 119b
3,7,11-Trimethyldodeca-1,6,10-trien-3-ol
Methylvinylhomogeranyl carbinol
FEMA No. 2772
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Sesquiterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Sesquiterpenoids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Farsesane sesquiterpenoid - Sesquiterpenoid - Tertiary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 222.372 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 7 |
| Complexity | 269 |
| Monoisotopic Mass | 222.198 |
| Exact Mass | 222.198 |
| XLogP | 4.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9559 |
| Human Intestinal Absorption | HIA+ | 0.9792 |
| Caco-2 Permeability | Caco2+ | 0.7312 |
| P-glycoprotein Substrate | Substrate | 0.5431 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6661 |
| Non-inhibitor | 0.6413 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8919 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4009 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8736 |
| CYP450 2D6 Substrate | Non-substrate | 0.8608 |
| CYP450 3A4 Substrate | Substrate | 0.5516 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6869 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8044 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9466 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8324 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8586 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8513 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8464 |
| Non-inhibitor | 0.8510 | |
| AMES Toxicity | Non AMES toxic | 0.9185 |
| Carcinogens | Non-carcinogens | 0.5830 |
| Fish Toxicity | High FHMT | 0.9575 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9112 |
| Honey Bee Toxicity | High HBT | 0.8326 |
| Biodegradation | Ready biodegradable | 0.5907 |
| Acute Oral Toxicity | III | 0.9000 |
| Carcinogenicity (Three-class) | Non-required | 0.6570 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1456 | LogS |
| Caco-2 Permeability | 1.3501 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6795 | LD50, mol/kg |
| Fish Toxicity | 0.2803 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3477 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| A study on accumulation of volatile organic compounds during ochratoxin a biosynthesis and characterization of the correlation in Aspergillus carbonarius isolated from grape and dried vine fruit. | Food Chem | 2017 Jul 15 | 28274458 |
| Larvicidal activity of Magnolia denudata seed hydrodistillate constituents and related compounds and liquid formulations towards two susceptible and two wild mosquito species. | Pest Manag Sci | 2016 May | 26085316 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]