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Rescinnamine

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Chemistry

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Also known as: Recinnamine, Reserpinene, Trimethoxycinnamoyl methyl reserpate, Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate, Ncgc00016787-01, 3,4,5-trimethoxycinnamoyl methyl reserpate

Molecular Formula

C₃₅H₄₂N₂O₉

Molecular Weight

634.7 g/mol

InChI Key

SZLZWPPUNLXJEA-LAFLMMDJSA-N

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.

1 2D Structure

Rescinnamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

2.1.2 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

2.1.3 InChI Key

SZLZWPPUNLXJEA-LAFLMMDJSA-N

2.1.4 Canonical SMILES

COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=CC(=C(C(=C6)OC)OC)OC

2.1.5 Isomeric SMILES

CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=CC(=C(C(=C6)OC)OC)OC

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Recinnamine

2. Reserpinene

3. Trimethoxycinnamoyl Methyl Reserpate

4. Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

5. Ncgc00016787-01

6. 3,4,5-trimethoxycinnamoyl Methyl Reserpate

7. Cas-24815-24-5

8. Prestwick0_000568

9. Prestwick1_000568

10. Dsstox_cid_3554

11. Dsstox_rid_77079

12. Dsstox_gsid_23554

13. Spbio_002575

14. Chembl3182071

15. Tox21_110611

16. Db01180

17. Q27164665

18. (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic Acid Methyl Ester

2.3 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₄₂N₂O₉
Molecular Weight	634.7 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	11
Exact Mass	634.28903092 g/mol
Monoisotopic Mass	634.28903092 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1080
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	1
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of hypertension.

5 Pharmacology and Biochemistry

5.1 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.

5.2 Mechanism of Action

Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.

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