N-Benzoyl-D-phenylalaninol
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| Category | Others |
| Catalog number | BBF-05206 |
| CAS | 5267-65-2 |
| Molecular Weight | 255.31 |
| Molecular Formula | C16H17NO2 |
| Purity | >95% by HPLC |
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Specification
| Related CAS | 4503-96-2 (L-configuration) |
| Synonyms | Benzamide, N-[(1R)-1-(hydroxymethyl)-2-phenylethyl]-; N-((R)-1-Hydroxymethyl-2-phenyl-ethyl)-benzamide; N-benzoyl(phenylalaninol); Bz-D-Phe-ol; (R)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide |
| Storage | Store at -20°C |
| IUPAC Name | N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]benzamide |
| Canonical SMILES | C1=CC=C(C=C1)CC(CO)NC(=O)C2=CC=CC=C2 |
| InChI | InChI=1S/C16H17NO2/c18-12-15(11-13-7-3-1-4-8-13)17-16(19)14-9-5-2-6-10-14/h1-10,15,18H,11-12H2,(H,17,19)/t15-/m1/s1 |
| InChI Key | RFYNAVYPYXLVOM-OAHLLOKOSA-N |
Properties
| Boiling Point | 513.1±43.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. [Anti-complement alkaloids from whole plants of Viola yedoensis]
Dong-Sheng Du, Zhi-Hong Cheng, Dao-Feng Chen Zhongguo Zhong Yao Za Zhi. 2017 Dec;42(24):4794-4800. doi: 10.19540/j.cnki.cjcmm.20170928.012.
Fifteen alkaloids were isolated from the 95% ethanol extract of the whole plants of Viola yedoensis by various column chromatographic techniques such as silica gel and Sephadex LH-20. Their structures were identified as neoechinulin A(1),N-benzoyl-L-p-hydroxy-phenylalaninol(2),aurantiamide acetate(3),aurantiamide(4),anabellamide(5),trichosanatine(6),indole-3-carboxylic acid methyl ester(7),3-carboxyindole(8),N-trans-feruloyl-tyramine(9),paprazine(10),7'-(3', 4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide(11),cannabisin F(12),N-(4-hydroxyphenethyl)octacosanamide(13),N-(4-hydroxyphenethyl)hexacosanamide(14)and N-benzoyl-L-phenylalaninol(15). All the compounds except 3 and 4 were isolated from this plant for the first time. These alkaloids exhibited anti-complement activity against the classical pathway(CP)and the alternative pathway(AP)with the CH50 and AP50 values ranging from 0.12 to 0.33 g·L⁻¹ and 0.22 to 0.50 g·L⁻¹, respectively. Preliminary mechanism study using complement-depleted sera showed that these alkaloids acted on different complement components in the complement activation cascade.
2. [Study on chemical constituents of petroleum ether portion from seed of Picria felterrae]
Qin Qiu, Fei-Fei Cen, Han-Shen Zhen Zhong Yao Cai. 2013 Feb;36(2):230-2.
Objective: To study the chemical constituents of petroleum ether portion from Seed of Picria felterrae. Methods: The chemical constituents were extracted and isolated with solvent and chromatography, and the chemical structures were determined on the basis of physicochemical properties and spectral data (UV, IR, 1H-NMR, 13C-NMR, MS). Results: Six chemical constituents were identified as follows: chrysophanol (I), 1-hydroxy-6-methyl-anthraquinone (II), beta-sitosterol (III), betulin (IV), N-benzoyl-phenylalanyl-L-phenylalaninol acetate (V) and picfeltarraenone I (VI). Conclusion: Compounds I, II and IV are isolated from this plant for the first time.
3. In vitro metabolism and in vivo pharmacokinetics of bentysrepinine (Y101), an investigational new drug for anti-HBV-infected hepatitis: focus on interspecies comparison
Huirong Fan, Aijie Zhang, Cuiping Liao, Yuanhui Yang, Lihua Zhang, Jianfeng Liu, Yuanyuan Xia, Duanyun Si, Shiqi Dong, Changxiao Liu Xenobiotica. 2020 Apr;50(4):468-478. doi: 10.1080/00498254.2019.1646946. Epub 2019 Sep 24.
The objective of this study was to clarify the species differences of pharmacokinetics of Y101 (N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl]-l-phenylalaninol hydrochloride), a derivative of herbal ingredient with anti-HBV hepatitis activity, in rats, dogs, monkeys and humans.The metabolic stability and metabolite identification studies using liver microsomes in vitro, plasma protein binding using a rapid equilibrium dialysis in vitro, pharmacokinetic studies in vivo were carried out to evaluate the interspecies differences. The toxicokinetic study in monkeys was also investigated.The metabolic profiles were similar in monkeys and humans, which were significant different from rats and dogs in vitro. In vitro plasma protein binding showed no major differences between species with medium to high protein binding rates. After single oral dose to rats, dogs, and monkeys, the absolute oral bioavailability of Y101 was 44.9%, 43.1%, and 19.2%, respectively. There was no accumulation for Y101 toxicokinetics in monkeys after oral administration for 90 d.The metabolic profiles indicated monkey was the very animal model for preclinical safety evaluation of Y101. Our results have demonstrated the favorable pharmacokinetics profile of Y101, which supports the clinical trials in humans.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
