Dehydrozingerone
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Basic Info
| Common Name | Dehydrozingerone(F08682) |
| 2D Structure | |
| FRCD ID | F08682 |
| CAS Number | 1080-12-2 |
| PubChem CID | 5354238 |
| Formula | C11H12O3 |
| IUPAC Name | (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one |
| InChI Key | AFWKBSMFXWNGRE-ONEGZZNKSA-N |
| InChI | InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+ |
| Canonical SMILES | CC(=O)C=CC1=CC(=C(C=C1)O)OC |
| Isomeric SMILES | CC(=O)/C=C/C1=CC(=C(C=C1)O)OC |
| Wikipedia | Dehydrozingerone |
| Synonyms |
Dehydrozingerone
Feruloylmethane
1080-12-2
Vanillalacetone
4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
Dehydro(O)-paradol
Vanillylidene acetone
MHSK
Dehydrogingerone
4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
|
| Classifies |
Food Additive
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Cinnamic acids and derivatives |
| Subclass | Hydroxycinnamic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Hydroxycinnamic acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Hydroxycinnamic acid or derivatives - Methoxyphenol - Phenoxy compound - Phenol ether - Styrene - Methoxybenzene - Anisole - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - Enone - Alpha,beta-unsaturated ketone - Acryloyl-group - Ketone - Ether - Organic oxygen compound - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 192.214 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 223 |
| Monoisotopic Mass | 192.079 |
| Exact Mass | 192.079 |
| XLogP | 1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| 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+ | 0.7451 |
| Human Intestinal Absorption | HIA+ | 0.9971 |
| Caco-2 Permeability | Caco2+ | 0.9199 |
| P-glycoprotein Substrate | Non-substrate | 0.6264 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7625 |
| Non-inhibitor | 0.8157 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8949 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8861 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7572 |
| CYP450 2D6 Substrate | Non-substrate | 0.8288 |
| CYP450 3A4 Substrate | Non-substrate | 0.5905 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5704 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9550 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9267 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6309 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8021 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6804 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9675 |
| Non-inhibitor | 0.9396 | |
| AMES Toxicity | Non AMES toxic | 0.8820 |
| Carcinogens | Non-carcinogens | 0.8599 |
| Fish Toxicity | High FHMT | 0.8808 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9784 |
| Honey Bee Toxicity | High HBT | 0.8193 |
| Biodegradation | Not ready biodegradable | 0.5324 |
| Acute Oral Toxicity | III | 0.8684 |
| Carcinogenicity (Three-class) | Non-required | 0.5972 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2392 | LogS |
| Caco-2 Permeability | 1.5193 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7858 | LD50, mol/kg |
| Fish Toxicity | 1.4715 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7499 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Radioprotective effects of Zingiber officinale Roscoe (ginger): past, present and future. | Food Funct | 2012 Jul | 22596078 |