Page last updated: 2024-12-08

(1r,5s)-4-methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-one

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

Description

You're describing a specific organic molecule, (1R,5S)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-one. Let's break down its structure and why it might be important in research.

**Structure:**

* **Bicyclo[3.1.0]hexane:** This tells us the core structure is a six-membered ring with a three-carbon bridge.
* **Hex-3-en-2-one:** This indicates a double bond at position 3 and a ketone (C=O) at position 2 of the ring.
* **4-Methyl:** A methyl group (CH3) is attached to carbon 4 on the ring.
* **1-propan-2-yl:** A propyl group with the branching at the second carbon (isopropyl) is attached to carbon 1 on the ring.
* **(1R,5S):** This indicates the absolute stereochemistry of the molecule. The R and S designations refer to the configuration of chiral centers at carbon 1 and 5 of the bicyclic system, respectively.

**Why it Might Be Important in Research:**

Without specific details about the research context, it's difficult to definitively state its importance. However, molecules with this general structure could be relevant in various fields, such as:

* **Medicinal Chemistry:** The bicyclic system, double bond, and ketone group could provide a scaffold for creating potential drug candidates. The specific substituents (methyl and isopropyl) might influence interactions with biological targets.
* **Organic Synthesis:** The compound's structure could serve as a starting material or intermediate in the synthesis of more complex molecules with potential applications in materials science, catalysis, or other areas.
* **Natural Products Chemistry:** This type of structure is sometimes found in naturally occurring compounds with biological activity, making it interesting for investigating the structure-activity relationships of natural products.

**To understand the specific importance of this molecule, you would need more information about the research project in which it is being investigated.**

**Note:** The molecule you described is a chiral molecule due to the presence of chiral centers. The stereochemistry (R/S) designation is crucial to understanding its specific properties and interactions.

(1R,5S)-4-methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-one: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID442504
CHEBI ID9860
SCHEMBL ID435454
MeSH IDM0557392

Synonyms (21)

Synonym
(-)-umbellulone
C09911 ,
umbellulone
546-78-1
AC1L9CYT ,
(1r,5s)-4-methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-one
(r)-umbellulone
SCHEMBL435454
CHEBI:9860
(1r,5s)-1-isopropyl-4-methyl-bicyclo[3.1.0]hex-3-en-2-one
surecn435454
NCGC00485432-01
HY-135013
(1r,5s)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-one
DTXSID301016986
[1r,5s,(-)]-4-methyl-1-isopropylbicyclo[3.1.0]hexa-3-ene-2-one
CS-0109051
MS-22850
(1r,5s)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one
umbellol
AKOS040740954

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ketoneA compound in which a carbonyl group is bonded to two carbon atoms: R2C=O (neither R may be H).
[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 (5)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (66.67)24.3611
2020's3 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.25

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 Index12.25 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]