Natural Product (NP) Details

General Information of the NP (ID: NP8600)
Name
Yohimbine
Synonyms
Yohimbine; Yohimbin; Quebrachin; Quebrachine; 146-48-5; Corynine; APHRODINE; Yohimbic acid methyl ester; Aphrosol; (+)-Yohimbine; Johimbin; Actibine; UNII-2Y49VWD90Q; 17-Hydroxyyohimban-16-carboxylic acid methyl ester; CHEMBL15245; 2Y49VWD90Q; 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester; CHEBI:10093; (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester; methyl 17alpha-hydroxyyohimban-16alpha-carboxylate; Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-; DSSTox_CID_20130; DSSTox_RID_79446; DSSTox_GSID_40130; methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate; YOHIMBINE CHLORIDE; CHEMBL537669; Yohimbine (DCF); CAS-146-48-5; methyl (1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride; methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate; methyl hydroxy[?]carboxylate; EINECS 205-672-0; BRN 0097276; trans-Quinolizidine yohimbine; YOHIMBE HYDROCHLORIDE; CCRIS 9415; SR-01000075297; Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.; Yohimbe bark extract; NSC19509; methyl (2S,13bS,14aS,1R,4aR)-2-hydroxy-1,2,3,4,5,8,14,13b,14a,4a-decahydrobenz o[1,2-g]indolo[2,3-a]quinolizinecarboxylate; Prestwick0_000584; Prestwick1_000584; Prestwick2_000584; Prestwick3_000584; Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester; Yohimbe Extract Yohimbine; cid_6169; cid_8969; Lopac0_001210; SCHEMBL33954; BSPBio_000428; BSPBio_001236; GTPL102; KBioGR_000576; KBioSS_000576; 4-25-00-01237 (Beilstein Handbook Reference); MLS000728591; SPBio_002647; BPBio1_000472; Yohimbol-16alpha-carboxylic acid, methyl ester (6CI); DTXSID9040130; BCBcMAP01_000032; KBio2_000576; KBio2_003144; KBio2_005712; KBio3_001031; KBio3_001032; Bio1_000455; Bio1_000944; Bio1_001433; Bio2_000458; Bio2_000938; HMS1362N17; HMS1792N17; HMS1990N17; HMS2089G19; HMS2234C18; ZINC3860825; Tox21_110019; BDBM50013515; BDBM50203564; MFCD00005093; AKOS015902024; Tox21_110019_1; Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester; Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI); CCG-205284; CS-5173; DB01392; GS-5751; MCULE-1043513122; SDCCGSBI-0051177.P002; IDI1_002213; MRF-0000020; SMP1_000320; NCGC00013260-01; NCGC00025018-05; NCGC00025018-06; NCGC00025018-07; NCGC00025018-10; NCGC00025018-11; NCGC00025018-17; HY-12715; SMR000470778; 17a-hydroxy-16a-methoxycarbonyl-yohimbane; 65Y190; C09256; D08685; Q412226; SR-01000075297-5; BRD-K35586044-001-02-6; BRD-K35586044-003-03-0; BRD-K35586044-003-11-3; Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)- (9CI); (1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester hydrochloride; 103834-06-6
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Species Origin Corynanthe johimbe ...     Click to Show/Hide
Corynanthe johimbe
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Rubiaceae
Genus: Corynanthe
Species: Corynanthe johimbe
Disease Erectile dysfunction [ICD-11: HA01] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C21H26N2O3
PubChem CID
8969
Canonical SMILES
COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
InChI
1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChIKey
BLGXFZZNTVWLAY-SCYLSFHTSA-N
CAS Number
CAS 146-48-5
ChEBI ID
CHEBI:10093
Herb ID
HBIN048645
SymMap ID
SMIT09771
TCMSP ID
MOL008488
TTD Drug ID
D0H4JM
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Imipramine      Depression     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     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		 Down-regulation Expression ADRA2A  Molecule Info 
Pathway MAP
Down-regulation Expression HTR2C  Molecule Info 
Pathway MAP
Down-regulation Expression SSTR1  Molecule Info 
Pathway MAP
                    In-vivo Model Animals received yohimbine (2 mg/kg) 30 min prior to administration of imipramine(20 mg/kg) (Y + I group) or received vehicle treatment (Ctl group), once a day for seven consecutive days in adult male Wistar rats (250-400 g, 2-3 months of age) and adult male nestin-GFP transgenic mice (25-35 g, 2-3 months of age).
                    Experimental
                    Result(s)		 Yohimbine and Imipramine combination treatment enhanced the quiescent neural progenitor pool in the hippocampal neurogenic niche similar to ECS, and distinct from chronic imipramine treatment.
Target and Pathway
Target(s) Adrenergic receptor Alpha-2 (ADRA2)  Molecule Info  [3]
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: 102).
Reference 2 Hippocampal transcriptional and neurogenic changes evoked by combination yohimbine and imipramine treatment. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Aug 3;61:1-9.
Reference 3 Acute neurotoxicity after yohimbine ingestion by a body builder. Clin Toxicol (Phila). 2009 Sep;47(8):827-9.
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