Rescinnamine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Rescinnamine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Rescinnamine?

The molecule Rescinnamine presents a molecular formula of C35H42N2O9 and its IUPAC name is methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate.

Rescinnamine is a molecule that has been shown to be effective in the treatment of Alzheimer's disease. It is a small molecule that can cross the blood-brain barrier and bind to the beta-amyloid protein, which is a major component of the plaques that are found in the brains of Alzheimer's patients. Rescinnamine has been shown to reduce the levels of beta-amyloid in the brain and to improve cognitive function in Alzheimer's patients. There is currently no cure for Alzheimer's disease, and the available treatments only offer symptomatic relief. Rescinnamine represents a potential new approach to the treatment of this devastating disease..

3D structure

Cartesian coordinates

Geometry of Rescinnamine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Rescinnamine SZLZWPPUNLXJEA-QEGASFHISA-N chemical compound 2D structure molecule svg
Rescinnamine

 

Molecule descriptors

 
IUPAC namemethyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
InChI codeInChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
InChI KeySZLZWPPUNLXJEA-QEGASFHISA-N
SMILESCOC(=O)[C@H]1[C@H]2C[C@@H]3c4[nH]c5cc(OC)ccc5c4CCN3C[C@H]2C[C@@H](OC(=O)/C=C/c2cc(OC)c(OC)c(OC)c2)[C@@H]1OC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-11,17-DIMETHOXY-18-(((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPEN-1-YL)OXY)-YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER
  • 11,17-Dimethoxy-18-[[1-oxo-3-3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-3,20-yohimban-16-carboxylic acid methyl ester
  • 11,17alpha-Dimethoxy-18beta-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylic acid methyl ester
  • 24815-24-5
  • 3,4,5-Trimethoxycinnamic acid, methyl reserpate
  • 3,4,5-Trimethoxycinnamoyl methyl reserpate
  • 3,4,5-Trimethylcinnamic acid, ester with methyl reserpate
  • 3,4,5-Trimethylcinnamoyl methyl reserpate
  • 3,4,5-trimethoxycinnamic acid ester of methyl reserpate
  • 3,5-Trimethoxycinnamic acid, methyl reserpate
  • 3,5-Trimethoxycinnamoyl methyl reserpate
  • 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
  • 3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
  • 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
  • 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester), (E)-
  • ACon1_002115
  • AI3-52763
  • Anaprel
  • Apolon
  • Apoterin
  • Apoterin S
  • BPBio1_000392
  • BRN 0075328
  • BSPBio_000356
  • Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate
  • C06540
  • CCRIS 4711
  • Cartric
  • Cinamine
  • Cinatabs
  • Cinnaloid
  • Cinnasil
  • D00198
  • GTPL7098
  • HMS1569B18
  • HMS2096B18
  • HMS2234E08
  • HSDB 2176
  • HY-A0220
  • MEGxp0_001952
  • METHYL 3,4,5-TRIMETHOXYCINNAMOYL RESERPATE
  • MLS002153878
  • Methyl 18-O-(3,4,5-trimethoxycinnamoyl)reserpate
  • Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate
  • Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate
  • Methyl 1alpha,2beta,3alpha,4,4aalpha,5,7,8,13,13bbeta,14,14aalpha-dodecahydro-2alpha,11-dimethoxy-3beta-(3,4,5-trimethoxycinnamoyloxy)benz(g)indolo(2,3-a)quinolizine-1beta-carboxylate
  • Methyl reserpate 3,4,5-trimethoxycinnamic acid ester
  • Methyl trimethoxycinnamoylreserpate
  • Moderil
  • NCGC00179585-03
  • NCGC00179585-04
  • NCGC00179585-04_C35H42N2O9_Cinnaloid
  • NSC 15628
  • NSC-15628
  • NSC15628
  • Normorescina
  • O-(3,4,5-Trimethoxy-trans-cinnamoyl) methyl reserpate
  • Paresinan
  • Prestwick2_000568
  • Prestwick3_000568
  • Prestwick_558
  • Q409978
  • Q6W1F7DJ2D
  • Raupyrol
  • Raurescin
  • Raurescine
  • Recinnamine
  • Recitensina
  • Rescaloid
  • Rescamin
  • Rescidan
  • Rescin
  • Rescinamina
  • Rescinnamin
  • Rescinnamina
  • Rescinnamine
  • Rescinnamine (JAN/INN)
  • Rescinnaminum
  • Rescinpal
  • Rescisan
  • Rescitens
  • Resealoid
  • Resepinine (C35 alkaloid)
  • Reserpic acid methyl ester 3,4,5-trimethoxycinnamate
  • Reserpinene
  • Reserpinine
  • Reserpinine (C35 alkaloid)
  • Resipal
  • Reskinnamin
  • Rozex
  • SMR001233232
  • Scinnamina
  • Tenamine
  • Trimethoxy cinnamoyl reserpate de methyl
  • Trimethoxycinnamoyl methyl reserpate
  • Tsuruselpi S
  • Tuareg
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-(((2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-oxy)-, methyl ester, (3beta,16beta,17alpha,18beta(E),20alpha)-
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3b,16b,17a,18b,20a)-
  • Yohimban-16-carboxylic acid,17-dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
  • Yohimban-16-carboxylicacid,11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]oxy]-,methyl ester, (3b,16b,17a,18b,20a)-
  • methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
  • methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
  • methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-({(2E)-3-[3,4,5-tris(methyloxy)phenyl]prop-2-enoyl}oxy)yohimban-16-carboxylate
  • methyl 11,17alpha-dimethoxy-18beta-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3beta,20alpha-yohimban-16beta-carboxylate
  • rescinnamine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4097185
  • UNII-Q6W1F7DJ2D
  • BRD-K52930707-001-02-2
  • BRD-K52930707-001-04-8
  • DTXSID3023554
  • CHEMBL1668
  • CHEBI:28572
  • CHEBI:92923
  • EINECS 246-471-8
  • SCHEMBL181966

Physico-Chemical properties

IUPAC namemethyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Molecular formulaC35H42N2O9
Molecular weight634.716
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity175.23
LogP4.5
Topological polar surface area117.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.