(6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-[1]benzopyrano[3,4-b][1]benzopyran-12-one profile

You're describing a compound that is a synthetic analog of **cannabidiol (CBD)**, a non-psychoactive component of the cannabis plant. It's a bit of a mouthful to say the full chemical name, so let's break it down and understand its importance in research:

**What is it?**

* **(6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-[1]benzopyrano[3,4-b][1]benzopyran-12-one:** This is the IUPAC name, a precise way to describe its chemical structure.
* **Key features:**
* **Similar to CBD:** It shares a similar core structure with CBD, specifically the [1]benzopyrano[3,4-b][1]benzopyran core.
* **Modifications:** It has modifications compared to CBD:
* **Methoxy groups (OCH3) at positions 2 and 3:** These are attached to the aromatic rings.
* **Hydroxy group (OH) at position 9:** This is also on an aromatic ring.
* **Prenyl group (3-methylbut-2-enyl) at position 8:** This is a branched chain attached to the core.
* **Ketone group (C=O) at position 12:** This is a double-bonded oxygen, potentially affecting the molecule's properties.

**Why is it important for research?**

This modified CBD analog is being investigated for several reasons:

* **Exploring Structure-Activity Relationships:** Scientists are interested in understanding how specific modifications to the CBD molecule affect its pharmacological properties. This compound, with its unique combination of functional groups, can provide insights into:
* **Potency:** Does it have stronger or weaker effects than CBD?
* **Selectivity:** Does it interact with specific targets in the body differently than CBD?
* **Pharmacokinetic properties:** How is it absorbed, metabolized, and eliminated?

* **Potential Therapeutic Benefits:** Like CBD, this compound might exhibit therapeutic potential. It could be investigated for:
* **Anti-inflammatory effects:** CBD is known for its anti-inflammatory properties.
* **Neuroprotective effects:** CBD has been researched for its potential to protect nerve cells.
* **Anti-cancer effects:** Some preliminary studies suggest CBD might have anticancer effects.

* **Overcoming Limitations of CBD:** CBD has some limitations, including poor bioavailability (it doesn't absorb well into the body) and potential for drug interactions. This analog could address these issues:
* **Improved Bioavailability:** The modifications might improve its absorption and utilization in the body.
* **Reduced Drug Interactions:** The changes in structure might alter its interactions with other drugs, potentially making it safer.

**Important Note:** It's crucial to understand that research on this compound is still in its early stages. More studies are needed to determine its safety, efficacy, and potential therapeutic benefits.

**In Summary:** This modified CBD analog is a promising research tool for understanding the structure-activity relationships of cannabinoids and exploring potential therapeutic benefits. However, more research is necessary to validate its safety and efficacy.

ID Source	ID
PubMed CID	6708539
CHEMBL ID	2181295
CHEBI ID	92599
SCHEMBL ID	752362

Synonym
KBIO1_001113
DIVK1C_006169
SDCCGMLS-0066410.P001
SPECTRUM_000647
SPECTRUM5_000303
BSPBIO_001749
KBIOGR_002203
KBIO2_001127 ,
KBIO2_006263
KBIO3_001249
KBIOSS_001127
KBIO2_003695
SPECTRUM2_000396
SPECTRUM4_001512
SPBIO_000611
SPECTRUM3_000195
SPECPLUS_000073
SPECTRUM200851
(6as,12as)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6h-chromeno[3,4-b]chromen-12-one
rotenonic acid
CHEMBL2181295
CCG-38667
BRD-K34330170-001-01-8
SCHEMBL752362
CHEBI:92599
(6as,12as)-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-butenyl)-6a,12a-dihydrochromeno[3,4-b]chromen-12(6h)-one
GBVCHRDRVDOMQV-RTWAWAEBSA-N
(6as,12as)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6h-[1]benzopyrano[3,4-b][1]benzopyran-12-one
Q27164316

Class	Description
rotenones	Members of the class of rotenoid which consists of a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton and its substituted products.
[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 (7)

Assay ID	Title	Year	Journal	Article
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID708845	Cytotoxicity against human H1299 cells after 3 days by MTS assay	2012	Journal of medicinal chemistry, Dec-27, Volume: 55, Issue:24	Design, synthesis, and biological evaluation of novel deguelin-based heat shock protein 90 (HSP90) inhibitors targeting proliferation and angiogenesis.
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID1660528	Inhibition of complex 1 in bovine heart mitochondrial membranes in presence of NADH	2020	Journal of natural products, 06-26, Volume: 83, Issue:6	Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells.
AID1437927	Cytotoxicity against mouse L5178Y cells by MTT assay	2017	Journal of natural products, 01-27, Volume: 80, Issue:1	Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa.
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal 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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	5 (83.33)	24.3611
2020's	1 (16.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (16.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	5 (83.33%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.59	2	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
rotenolone rotenolone: decomposition product of rotenone; RN given refers to (2 alpha,6a beta,12a beta)-isomer	2.25	1	organic molecular entity	metabolite
amorphigenin amorphigenin: RN given refers to (2R-(2alpha,6aalpha,12aalpha))-isomer; structure given in first source	2.25	1	rotenones
deguelin deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.	2.83	3	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite
tephrosin tephrosin: RN given for (7aR-cis)-isomer; has insecticidal activity; structure in first source. tephrosin : A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities.	2.25	1	aromatic ether; cyclic ketone; organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; pesticide
moxifloxacin Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.	2.15	1	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
alpha-toxicarol alpha-toxicarol: from the roots of Derris trifoliata; structure in first source	2.15	1	isoflavanones
xanthoangelol xanthoangelol: from Angelica keiskei; structure given in first source; RN given refers to (E,E)-isomer	2.15	1
Dehydrodeguelin,7a,13a-Didehydrodeguelin [no description available]	2.51	2	rotenones
geldanamycin [no description available]	2.07	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound	antimicrobial agent; antineoplastic agent; antiviral agent; cysteine protease inhibitor; Hsp90 inhibitor
amorphastilbol amorphastilbol: dual PPARalpha/gamma agonist from Amorpha species	2.15	1
amorfrutin a amorfrutin A: an antidiabetic agent that inhibits NF-kappaB activation; structure in first source	2.15	1	stilbenoid
2-(3,4-dimethoxyphenyl)-1-(5-methoxy-2,2-dimethyl-2h-chromen-6-yl)ethanone 2-(3,4-dimethoxyphenyl)-1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone: an Hsp90 inhibitor; structure in first source	2.07	1

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	3.03	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.03	1
Anemia, Fanconi [description not available]	2.13	1
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1
Germinoblastoma [description not available]	2.15	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.15	1
Cancer of Prostate [description not available]	2.25	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.25	1

(6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-[1]benzopyrano[3,4-b][1]benzopyran-12-one

Cross-References

Synonyms (29)

Drug Classes (1)

Bioassays (7)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.56

Study Types

(6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-[1]benzopyrano[3,4-b][1]benzopyran-12-one

Cross-References

Synonyms (29)

Drug Classes (1)

Bioassays (7)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.56

Study Types

Related Drugs (13)

Related Conditions (8)