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: 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

NAMES AND DATABASE IDS

Names

• 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[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]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[11.8.0.0^2,10.0^4,9.0^15,20]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

Database IDs

• 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

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.290113
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.2718618
• LogD (pH = 7.4): 3.816317
• Log P: 4.070087
• Molar Refractivity: 171.1642 cm^3
• Polarizability: 67.82844 Å^3
• Polar Surface Area: 117.78 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.48
• LOG S: -5.26
• Solubility (Water): 3.49e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.5

Pharmacology Properties

• Admin Routes: oral
• Legal Status: Rx-only

DETAILS

DrugBank - DB01180

• 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