Dihydrocapsaicin
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Basic Info
| Common Name | Dihydrocapsaicin(F01422) |
| 2D Structure | |
| FRCD ID | F01422 |
| CAS Number | 19408-84-5 |
| PubChem CID | 107982 |
| Formula | C18H29NO3 |
| IUPAC Name | N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide |
| InChI Key | XJQPQKLURWNAAH-UHFFFAOYSA-N |
| InChI | InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21) |
| Canonical SMILES | CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC |
| Isomeric SMILES | CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC |
| Synonyms |
Dihydrocapsaicin
19408-84-5
N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide
6,7-Dihydrocapsaicin
8-Methyl-N-vanillylnonanamide
CCRIS 1589
dihydro capsaicin
UNII-W9BV32M08A
8-methyl dihydrocapsaicin
Nonanamide, 8-methyl-N-vanillyl-
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 16:49 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Methoxyphenols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Methoxyphenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Carboximidic acid - Carboximidic acid derivative - Ether - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Organic nitrogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 307.434 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 10 |
| Complexity | 307 |
| Monoisotopic Mass | 307.215 |
| Exact Mass | 307.215 |
| XLogP | 4.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7088 |
| Human Intestinal Absorption | HIA+ | 0.9922 |
| Caco-2 Permeability | Caco2+ | 0.5616 |
| P-glycoprotein Substrate | Substrate | 0.6946 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8385 |
| Non-inhibitor | 0.6125 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7941 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9225 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7960 |
| CYP450 2D6 Substrate | Substrate | 0.5279 |
| CYP450 3A4 Substrate | Substrate | 0.6965 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9106 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8949 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8320 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5294 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7532 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8390 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9803 |
| Inhibitor | 0.6255 | |
| AMES Toxicity | AMES toxic | 0.8755 |
| Carcinogens | Non-carcinogens | 0.9062 |
| Fish Toxicity | High FHMT | 0.7659 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9861 |
| Honey Bee Toxicity | Low HBT | 0.6426 |
| Biodegradation | Not ready biodegradable | 0.8713 |
| Acute Oral Toxicity | III | 0.6752 |
| Carcinogenicity (Three-class) | Non-required | 0.7134 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2021 | LogS |
| Caco-2 Permeability | 1.1714 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2073 | LD50, mol/kg |
| Fish Toxicity | 1.5184 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6560 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous determination of capsaicin and dihydrocapsaicin for vegetable oiladulteration by immunoaffinity chromatography cleanup coupled with LC-MS/MS. | J Chromatogr B Analyt Technol Biomed Life Sci | 2016 May 15 | 26739369 |
| Fast method for capsaicinoids analysis from Capsicum chinense fruits. | Food Res Int | 2014 Oct | 30011708 |
| Quantification, antioxidant and antimicrobial activity of phenolics isolated fromdifferent extracts of Capsicum frutescens (Pimenta Malagueta). | Molecules | 2014 Apr 24 | 24879587 |
| Effects of dietary addition of capsicum extract on intake, water consumption, andrumen fermentation of fattening heifers fed a high-concentrate diet. | J Anim Sci | 2012 Jun | 22648751 |
| Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomalCYP450 enzyme activities in vitro and in vivo. | J Asian Nat Prod Res | 2012 | 22375877 |
| Preparative separation of capsaicin and dihydrocapsaicin from Capsicum frutescensby high-speed counter-current chromatography. | J Sep Sci | 2009 Sep | 19655324 |
| Mobility of heavy metals from soil into hot pepper fruits: a field study. | Bull Environ Contam Toxicol | 2009 Jan | 18758679 |
| Effects of capsaicin, dihydrocapsaicin, and curcumin on copper-induced oxidation of human serum lipids. | J Agric Food Chem | 2006 Aug 23 | 16910741 |