Natural Product (NP) Details

General Information of the NP (ID: NP1591)
Name
Reserpine
Synonyms
reserpine; 50-55-5; Serpalan; Serpasil; Serpivite; Apoplon; Hypersil; Alserin; Elserpine; Hiserpia; Raunervil; Raupasil; Rausedil; Rausedyl; Rauwasedin; Reserpin; Serpanray; Resine; Rivasin; Sandril; Serpate; (-)-Reserpine; Rau-Sed; Ascoserpina; Austrapine; Bioserpine; Enipresser; Eskaserpine; Helfoserpin; Hiposerpil; Maviserpin; Mayserpine; Mephaserpin; Purserpine; Rauserpine; Reserpamed; Reserpanca; Alkarau; Apsical; Banasil; Benazyl; Carditivo; Carrserp; Escaspere; Eserpine; Eskaserp; Hypersine; Idsoserp; Interpina; Lemiserp; Loweserp; Neoserfin; Neoserp; Quiescin; Raudiford; Raudixoid; Rauloydin; Raumorine; Raunorine; Raupoid; Raurine; Rausedan; Rauserpol; Rausingle; Rautrin; Rauvlid; Rauwilid; Rauwipur; Rauwoleaf; Rawilid; Resedrex; Reserbal; Resercaps; Resercen; Reserjen; Reserlor; Reserpal; Reserpene; Reserpex; Reserpil; Reserpina; Reserpoid; Respital; Restran; Riserpa; Roxinoid; Kitine; Raucap; Raugal; Raulen; Rausan; Reserp; Key-serpine; 3P Reserp; Crystoserpine; Neo-antitensol; Rauserpin-Alk; Deserpine; Ryser; Reserfia; 3,4,5-Trimethoxybenzoyl methyl reserpate; V-Serp; Carpacil; Gilucard; Klimanosid; Resaltex; Resedril; Reserpidefe; Recipin; Serpine; ENT 50146; Raunova; Residin; Serpivate; Rese-lar; Reser-ar; NCI-C50157; H 520; UNII-8B1QWR724A; Sedaraupina; Temposerpine; Eberpine; Raudixin; Reserpur; Residine; Resocalm; Resperine; Rezerpin; Sandron; Sedaraupin; Sedserp; Serfolia; Serolfia; Serpaloid; Serpasol; Serpazol; Serpena; Serpentil; Serpentina; Serpicon; Serpiloid; Serpogen; Serpoid; Serpone; Sertabs; Sertens; Sertina; Triserpin; Unilord; Serfin; Serpen; Roxel; Vio-Serpine; SK-Reserpine; Renese R; T-Serp; C33H40N2O9; MFCD00005091; CHEMBL772; Broserpine; R-e-s; Reserpinum; Sederaupin; Serpaneurona; Tefaserpina; Tenserpinie; Tepserpine; Eberspine; Reserpka; Resiatric; Resperin; Rivased; Rolserp; Roxynoid; Serpazil; Serpedin; Serpentin; Serpipur; Serpyrit; Sertensin; Serpil; Tempo-Reserpina; 8B1QWR724A; 50-55-5 (free); Mallopress; Rcra waste number U200; Hydropine; Hydroserp; Rauwita; .gamma.-Serpine; CHEBI:28487; Hydromox-R; Diurese-R; NSC59272; Metatensin #2; Metatensin #4; NSC-59272; component of Naquival; component of Regroton; Hydropres 25; Hydropres 50; Hydrosine 25; NSC-237659; (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester; methyl (1S,2R,3R,4aS,13bR,14aS)-2,11-dimethoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate; methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate; Usaf cb-27; component of Renese R; component of Metatensin; NCGC00091250-04; Hydroserpalan; Diupres 250; Diupres 500; l-Carpserp; component of Butiserpazide; DSSTox_CID_1237; Hydroserpine Plus; Hydroserpine #1; DSSTox_RID_76029; DSSTox_GSID_21237; Chloroserp-250; Chloroserp-500; Chloroserpin-250; Serpasil premix; Chloroserpine-500; Hydro-Reserpine-25; Hydro-Reserpine-50; Hydro-Fluserpine #1; l -Carpserp; Caswell No. 722A; Serp-AFD; Reserpina [INN-Spanish]; 3,5-Trimethoxybenzoyl methyl reserpate; (1S,2R,3R,4aS,13bR,14aS)-methyl 2,11-dimethoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate; methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate; methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-bis(methyloxy)-18-({[3,4,5-tris(methyloxy)phenyl]carbonyl}oxy)yohimban-16-carboxylate; SMR000059122; Yohimban-16-carboxylic acid,11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester,(3b,16b,17a,18b,20a)-; Apoplon (TN); CCRIS 550; Serpine (pharmaceutical); HSDB 213; Methyl reserpate 3,5-trimethyloxybenzoic acid; 11,17-Dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylic acid methyl ester; Methyl reserpate 3,5-trimethoxybenzoic acid ester; EINECS 200-047-9; RCRA waste no. U200; EPA Pesticide Chemical Code 123101; NSC 237659; BRN 0102014; AI3-50146; Reserpine/; WLN: T F6 D5 C666 EM ON&&TTTJ HO1 SOVR CO1 DO1 EO1& TO1 UVO1; Reserpine [USP:INN:BAN:JAN]; CAS-50-55-5; Reserpine,(S); Serpalan (TN); 3-.beta., 18-.beta.-hydroxy-11,17-.alpha.-dimethoxy-,methyl ester, 3,4,5-trimethoxybenzoate (ester); 3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy- methyl ester 3,4,5-trimethoxybenzoate (ester); 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-trimethoxybenzoate; methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}yohimban-16-carboxylate; Yohimban-16-carboxylic acid,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-; Prestwick_147; Methyl reserpate 3,4,5-trimethoxybenzoic acid ester; Reserpine, 99%; Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-; Spectrum_000109; Reserpic acid methyl ester 3,4,5-trimethoxybenzoate (ester); 79 more names available; 1263-94-1; Prestwick0_000875; Prestwick1_000875; Prestwick2_000875; Prestwick3_000875; Spectrum3_000894; Spectrum4_000989; Spectrum5_001415; R 0875; SCHEMBL2589; Lopac0_000073; BSPBio_000949; KBioGR_001397; KBioSS_000549; 4-25-00-01319 (Beilstein Handbook Reference); Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate 3,4,5-trimethoxybenzoate (ester); methyl dimethoxy-(3,4,5-trimethoxybenzoyl)oxy-[?]carboxylate; MLS002154046; MLS006011754; DivK1c_000012; SPECTRUM1500526; SPBio_002870; Reserpine (JP17/USP/INN); AMY591; BPBio1_001045; GTPL4823; MEGxp0_001904; DTXSID7021237; ACon1_000086; HMS500A14; KBio1_000012; KBio2_000549; KBio2_003117; KBio2_005685; KBio3_001808; AOB5791; NINDS_000012; HMS1570P11; HMS1920P04; HMS2092G05; HMS2097P11; HMS2234E24; HMS3260O07; HMS3413D20; HMS3677D20; HMS3714P11; HMS3884I21; Pharmakon1600-01500526; HY-N0480; Reserpine, Vetec(TM) reagent grade; RKL10049; ZINC3938746; Tox21_111107; Tox21_202395; Tox21_300537; Tox21_500073; ABP000583; BBL028800; BDBM50017712; ENT-50146; NSC237659; NSC757309; STK801975; AKOS000277559; Tox21_111107_1; CCG-204168; CS-1913; DB00206; KS-5106; LP00073; MCULE-9131256292; MCULE-9946449258; NSC-757309; SDCCGSBI-0050061.P005; IDI1_000012; NCGC00091250-01; NCGC00091250-02; NCGC00091250-03; NCGC00091250-05; NCGC00091250-06; NCGC00091250-07; NCGC00091250-08; NCGC00091250-09; NCGC00091250-10; NCGC00091250-12; NCGC00091250-14; NCGC00091250-25; NCGC00254489-01; NCGC00259944-01; NCGC00260758-01; 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester); AC-13142; methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate; NCI60_004446; SBI-0050061.P004; EU-0100073; Reserpine, crystallized, >=99.0% (HPLC); SW196458-3; UNM000011053801; C06539; D00197; J10192; 91098-EP2275420A1; 91098-EP2305219A1; AB01562943_01; 005R091; 146088-EP2287158A1; 146088-EP2292597A1; Q407841; Q-100566; BRD-K95921201-001-07-0; Methyl reserpate; 3,4,5-Trimethoxybenzoic acid ester; Reserpine, certified reference material, TraceCERT(R); Reserpine solution, 1 pg/muL in methanol: water (1:1); Reserpine, European Pharmacopoeia (EP) Reference Standard; Reserpine Standard for LC-MS, analytical standard, for LC-MS; Reserpine, United States Pharmacopeia (USP) Reference Standard; Reserpine, Pharmaceutical Secondary Standard; Certified Reference Material; (3?,16?,17?,18?,20?)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester; (3beta,16beta,17alpha,18beta,20alpha)-11,17-Dimethoxy-18- [(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxyl ic acid methyl ester; 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy- methyl ester 3,4,5-trimethoxybenzoate (ester) (8CI); methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(3,4,5-trimethoxyphenyl)carbonyloxy]-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
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Species Origin Rauvolfia serpentina ...     Click to Show/Hide
Rauvolfia serpentina
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Apocynaceae
Genus: Rauvolfia
Species: Rauvolfia serpentina
Disease Hypertension [ICD-11: BA00] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C33H40N2O9
PubChem CID
5770
Canonical SMILES
COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
InChI
1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
InChIKey
QEVHRUUCFGRFIF-MDEJGZGSSA-N
CAS Number
CAS 50-55-5
ChEBI ID
CHEBI:28487
Herb ID
HBIN042095
TTD Drug ID
D0J4JM
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Mitoxantrone + Verapamil     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CD80  Molecule Info 
Pathway MAP
Up-regulation Expression HLA-DRB5  Molecule Info 
Pathway MAP
Up-regulation Expression KLRK1  Molecule Info 
Pathway MAP
                    In-vitro Model YAC-1 CVCL_2244 Mouse lymphoma Mus musculus
B16-F10 CVCL_0159 Mouse melanoma Mus musculus
                    In-vivo Model For a xenograft model, Female C57BL/6 mice, 6-8 weeks of age, 18-20 g, were subcutaneously (s.c.) immunized in the abdominal region with 2x105, 5x105 or 1x106 B16F10 cells.
                    Experimental
                    Result(s)		 The B16F10 tumor cell vaccine treated with MIP in combination with RP and VP was safe and efficient.
Target and Pathway
Target(s) Synaptic vesicle amine transporter (SLC18A2)  Molecule Info  [3]
KEGG Pathway Synaptic vesicle cycle Click to Show/Hide
2 Serotonergic synapse
3 Dopaminergic synapse
4 Parkinson's disease
5 Cocaine addiction
6 Amphetamine addiction
7 Alcoholism
Panther Pathway Adrenaline and noradrenaline biosynthesis Click to Show/Hide
2 5HT1 type receptor mediated signaling pathway
3 5HT2 type receptor mediated signaling pathway
4 5HT3 type receptor mediated signaling pathway
5 5HT4 type receptor mediated signaling pathway
6 Dopamine receptor mediated signaling pathway
7 Nicotine pharmacodynamics pathway
8 CCKR signaling map ST
Reactome Norepinephrine Neurotransmitter Release Cycle Click to Show/Hide
2 Na+/Cl- dependent neurotransmitter transporters
WikiPathways Dopaminergic Neurogenesis Click to Show/Hide
2 Synaptic Vesicle Pathway
3 Neurotransmitter Release Cycle
4 Nicotine Activity on Dopaminergic Neurons
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4823).
Reference 2 Antitumor efficacy induced by a B16F10 tumor cell vaccine treated with mitoxantrone alone or in combination with reserpine and verapamil in mice. Exp Ther Med. 2011 Sep;2(5):911-916.
Reference 3 Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8.
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