Page last updated: 2024-12-11

(1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

That's a mouthful! Let's break down this chemical name and its significance.

**What is it?**

* **(1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester** is a complex organic molecule with a long and descriptive name.
* **Yohimban** refers to its core structure, a type of alkaloid found in the bark of the yohimbe tree.
* The name specifies the stereochemistry (spatial arrangement) of various atoms in the molecule, indicated by the prefixes like (1S) etc.
* It also details the presence of various functional groups:
* **Methoxy groups (-OCH3)** are attached at positions 6 and 18.
* **A trimethoxyphenyl group (-C6H2(OCH3)3)** is attached to the molecule via an oxo-(oxo means a carbonyl group, C=O) linkage.
* **A methyl ester (-COOCH3)** is at position 19.

**Why is it important for research?**

This compound, often referred to as **Yohimbine analog** or **Yohimbine derivative**, is important for research due to its potential:

* **Pharmacological Activity:** Yohimbine is known for its effects on the nervous system, especially as an alpha-2 adrenergic receptor antagonist. This class of molecules has potential applications in treating various conditions, including erectile dysfunction, depression, and anxiety.
* **Structure-Activity Relationships:** Synthesizing and studying analogs of yohimbine allows researchers to investigate how changes in molecular structure affect its pharmacological activity. This helps to understand the mechanism of action and potentially design more potent and selective drugs.
* **Drug Discovery:** By modifying the structure of yohimbine, researchers can potentially create novel compounds with improved therapeutic properties, overcoming limitations of the original molecule.

**Important Notes:**

* The exact biological activity of this specific yohimbine analog may not be known. Research is often ongoing in the field of drug development and modification.
* This molecule likely needs further investigation for its safety and efficacy before potential therapeutic applications.

**In summary:** This complex yohimbine analog holds potential for research in the fields of pharmacology, drug discovery, and medicinal chemistry. Further studies are needed to understand its properties and potential benefits.

Cross-References

ID SourceID
PubMed CID5701996
CHEMBL ID388848
CHEBI ID92652
SCHEMBL ID731599

Synonyms (43)

Synonym
DIVK1C_000200
KBIO1_000200
(-)-isoreserpine
yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (16beta,17alpha,18beta,20alpha)-
SPECTRUM_000004
IDI1_000200
SMP1_000292
3-epireserpine
482-85-9
nsc80138
3-isoreserpine
isoreserpine
BSPBIO_002712
SPECTRUM5_000924
methyl dimethoxy-(3,4,5-trimethoxybenzoyl)oxy-[?]carboxylate
BCBCMAP01_000242
KBIO3_002212
KBIO2_002912
KBIO2_000344
KBIOSS_000344
KBIO2_005480
SPBIO_001639
NINDS_000200
SPECTRUM3_001236
SPECTRUM2_001770
SPECTRUM300534
CHEMBL388848
HMS500J22
R0007
nsc 80138
20alpha-yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)
CCG-39604
BRD-K37080523-001-01-0
SCHEMBL731599
CHEBI:92652
DTXSID50858952
Q27164362
(1s,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester
20alpha-yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester) (8ci)
methyl (1s,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
EN300-19736137
methyl (1s,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(9),5,7-tetraene-19-carboxylate
AKOS040752126
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
yohimban alkaloid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID401301Reversal of P-gp-mediated multidrug resistance in human MCF/ADR cells assessed as ratio of adriamycin ED50 without drug to adriamycin ED50 with drug at 3.29 uM after 6 days by BCA assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Bicinchoninic acid protein assay in the determination of adriamycin cytotoxicity modulated by the MDR glycoprotein.
AID401299Reversal of P-gp-mediated multidrug resistance in human MCF/ADR cells assessed as ratio of adriamycin ED50 without drug to adriamycin ED50 with drug at 0.82 uM after 6 days by BCA assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Bicinchoninic acid protein assay in the determination of adriamycin cytotoxicity modulated by the MDR glycoprotein.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID401300Reversal of P-gp-mediated multidrug resistance in human MCF/ADR cells assessed as ratio of adriamycin ED50 without drug to adriamycin ED50 with drug at 1.64 uM after 6 days by BCA assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Bicinchoninic acid protein assay in the determination of adriamycin cytotoxicity modulated by the MDR glycoprotein.
AID697852Inhibition of electric eel AChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID697853Inhibition of horse BChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's4 (80.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.53

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.53 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]