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24815-24-5 molecular structure
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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

ChemBase ID: 1051
Molecular Formular: C35H42N2O9
Molecular Mass: 634.71598
Monoisotopic Mass: 634.28903093
SMILES and InChIs

SMILES:
O([C@@H]1[C@H]([C@@H]2[C@@H](CN3[C@H](C2)c2[nH]c4c(c2CC3)ccc(OC)c4)C[C@H]1OC(=O)C=Cc1cc(OC)c(OC)c(OC)c1)C(=O)OC)C
Canonical SMILES:
COc1ccc2c(c1)[nH]c1c2CCN2[C@@H]1C[C@H]1[C@@H](C2)C[C@H]([C@@H]([C@H]1C(=O)OC)OC)OC(=O)C=Cc1cc(OC)c(c(c1)OC)OC
InChI:
InChI=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/t20-,24+,26-,29-,31+,34+/m1/s1
InChIKey:
SZLZWPPUNLXJEA-LAFLMMDJSA-N

Cite this record

CBID:1051 http://www.chembase.cn/molecule-1051.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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 (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate
IUPAC Traditional name
rescinnamine
Brand Name
Anapral
Anaprel
Apolon
Apoterin
Apoterin S
Cartric
Cinamine
Cinatabs
Cinnaloid
Cinnasil
Moderil
Normorescina
Paresinan
Raupyrol
Raurescin
Raurescine
Recitensina
Rescaloid
Rescamin
Rescidan
Rescin
Rescinpal
Rescisan
Rescitens
Resealoid
Resipal
Reskinnamin
Rozex
Scinnamina
Tenamine
Tsuruselpi S
Tuareg
Synonyms
Methyl Trimethoxycinnamoylreserpate
Trimethoxycinnamoyl Methyl Reserpate
Recinnamine
Rescinnamin
Reserpinene
Reserpinin
Reserpinine
Rescinnamine
methyl (1''R'',15''S'',17''R'',18''R'',19''S'',20''S'')-6,18-dimethoxy-17-{[(2''E'')-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
CAS Number
24815-24-5
PubChem SID
160964514
46507786
PubChem CID
32681
5280954
CHEBI ID
28572
ATC CODE
C02AA01
CHEMBL
1668
Chemspider ID
4444446
DrugBank ID
DB01180
KEGG ID
D00198
Unique Ingredient Identifier
Q6W1F7DJ2D
Wikipedia Title
Rescinnamine

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.290113  H Acceptors
H Donor LogD (pH = 5.5) 2.2718618 
LogD (pH = 7.4) 3.816317  Log P 4.070087 
Molar Refractivity 171.1642 cm3 Polarizability 67.82844 Å3
Polar Surface Area 117.78 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five false 
Log P 4.48  LOG S -5.26 
Solubility (Water) 3.49e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Hydrophobicity(logP)
3.5 expand Show data source
Admin Routes
oral expand Show data source
Legal Status
Rx-only expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01180 external link
Item Information
Drug Groups approved
Description Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia. [Wikipedia]
Indication For the treatment of hypertension.
Pharmacology Used to treat hypertension. Rescinnamine inhibits angiotensin-converting enzyme. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex and general vasoconstriction, both of which lead to increases vascular resistance. By inhibiting angiotensin II, aldosterone reabsorption is decreased as well as vasoconstriction. This combined effect serves to decrease blood pressure.
Affected Organisms
Humans and other mammals
External Links
Wikipedia

REFERENCES

REFERENCES

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PATENTS

PATENTS

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