Page last updated: 2024-11-12

14-deoxyandrographolide

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Description

14-deoxyandrographolide: from Andrographis paniculata; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
AndrographisgenusA plant genus of the family ACANTHACEAE. Members contain andrographolide and other DITERPENES and androechin, a CHALCONE.[MeSH]AcanthaceaeA plant family of the order Lamiales. It is characterized by simple leaves in opposite pairs, cystoliths (enlarged cells containing crystals of calcium carbonate), and bilaterally symmetrical and bisexual flowers that are usually crowded together. The common name for Ruellia of wild petunia is easily confused with PETUNIA.[MeSH]

Cross-References

ID SourceID
PubMed CID11624161
CHEMBL ID415768
MeSH IDM0295878

Synonyms (23)

Synonym
CHEMBL415768
14-deoxyandrographolide
4-[2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethyl]-2h-furan-5-one
4176-97-0
AC-34626
2(5h)-furanone,3-[2-[(1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-
3-(2-((1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)furan-2(5h)-one
AKOS027324400
np-011179
2(5h)-furanone, 3-(2-((1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)-
ad-04130-4
3-(2-((1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)-2(5h)-furanone
WLN91FAQ6Z ,
ent-3beta-hydroxy-8(17),13(14)-labdadiene-16,15-olide 14-deoxyandrographolide
DTXSID80904638
F21512
unii-wln91faq6z
CS-0032748
HY-N4323
MS-25054
3-[2-[(1r,4abeta)-2-methylene-5alpha-(hydroxymethyl)-5,8aalpha-dimethyl-6alpha-hydroxydecalin-1alpha-yl]ethyl]-2,5-dihydrofuran-2-one
3-{2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethy l-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5h)-furanone
A913391
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (44)

Assay IDTitleYearJournalArticle
AID249077Concentration causing 50% inhibition of cancer cell growth against human prostate DU145 cell line2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID1408137Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of TGFbeta1-induced increase in FN mRNA level at 500 nM preincubated for 1 hr followed by TGFbeta-1 addition measured after 24 hrs by qRT-PCR method2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID776229Antioxidant activity assessed as decrease in superoxide anions level by measuring formation of formazone at 200 ug/ml after 30 mins by spectrophotometric analysis relative to control2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
AID1204064Cytotoxicity against human NTUB1 cells after 48 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation on cytotoxic activities.
AID1204903Cytotoxicity against human Jurkat T cells assessed as apoptosis after 24 hrs by annexin V-FLUOS/propidium iodide staining-based flow cytometric analysis2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Specificity and inhibitory mechanism of andrographolide and its analogues as antiasthma agents on NF-κB p50.
AID776228Antioxidant activity assessed as decrease in hydroxyl radicals level by measuring formation of malondialdehyde at 200 ug/ml after 90 mins by spectrophotometric analysis relative to control2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
AID1544507Cytotoxicity in mouse BV2 cells assessed as reduction in cell viability2019Bioorganic & medicinal chemistry, 06-01, Volume: 27, Issue:11
Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.
AID776252Antidyslipidemic activity in Charles foster rat assessed as decrease in triton WR-1339-induced total cholesterol level in plasma at 100 mg/kg, po after 18 hrs relative to triton-treated rat2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
AID1544494Lipophilicity, log P of the compound2019Bioorganic & medicinal chemistry, 06-01, Volume: 27, Issue:11
Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.
AID249072Concentration causing 50% inhibition of cancer cell growth against human CNS U251 cell line2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID1204067Cytotoxicity against human NP14 cells after 48 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation on cytotoxic activities.
AID1408136Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of TGFbeta1-induced increase in alpha-SMA mRNA level at 500 nM preincubated for 1 hr followed by TGFbeta-1 addition measured after 24 hrs by qRT-PCR method2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID380100Antimicrobial activity against Bacillus subtilis at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID645483Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 100 uM after 24 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
Microbial transformation of deoxyandrographolide and their inhibitory activity on LPS-induced NO production in RAW 264.7 macrophages.
AID1204909Inhibition of TNF-alpha-stimulated NF-kappaB p50 (unknown origin) expressed in HEK293 cells preincubated for 4 hrs followed by TNF-alpha challenge measured after 24 hrs by secreted alkaline phosphatase reporter assay2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Specificity and inhibitory mechanism of andrographolide and its analogues as antiasthma agents on NF-κB p50.
AID1544503Neuroprotective activity against 6-OHDA -induced toxicity in rat PC12 cells assessed as increase in cell viability at 20 uM pretreated for 24 hrs followed by 6-OHDA challenge and measured after 24 hrs by MTT assay2019Bioorganic & medicinal chemistry, 06-01, Volume: 27, Issue:11
Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.
AID1408141Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of COL1A1 mRNA level at 500 nM measured after 24 hrs by qRT-PCR method2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID1204906Binding affinity to 6His-tagged recombinant human NF-kappaB p50 N-terminal domain expressed in Escherichia coli BL21 (DE3) up to 10:1 compound to protein molar ratio after 2 hrs by mass spectrometric analysis2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Specificity and inhibitory mechanism of andrographolide and its analogues as antiasthma agents on NF-κB p50.
AID249073Concentration causing 50% inhibition of cancer cell growth against human lung H522 cell line2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID380103Antimicrobial activity against Micrococcus luteus at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID380105Antimicrobial activity against Candida sake at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID1544501Neuroprotective activity against H2O2-induced toxicity in rat PC12 cells assessed as increase in cell viability at 20 uM pretreated for 24 hrs followed by H2O2 challenge and measured after 24 hrs by MTT assay2019Bioorganic & medicinal chemistry, 06-01, Volume: 27, Issue:11
Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.
AID380102Antimicrobial activity against Escherichia coli at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID249076Concentration causing 50% inhibition of cancer cell growth against human ovarian SKOV3 cell line2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID1408132Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of cell proliferation after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID1408138Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of TGFbeta1-induced increase in COL1A1 mRNA level at 500 nM preincubated for 1 hr followed by TGFbeta-1 addition measured after 24 hrs by qRT-PCR method2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID249083Concentration causing 50% inhibition of cancer cell growth against human breast MCF-7/ADR cell line; nd = not done2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID776227Antioxidant activity assessed as reduction of microsomal lipid per-oxidation level by measuring formation of malondialdehyde at 200 ug/ml after 90 mins by spectrophotometric analysis relative to control2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
AID1204066Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation on cytotoxic activities.
AID249080Concentration causing 50% inhibition of cancer cell growth against human renal A498 cell line; nd = not done2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID380101Antimicrobial activity against Staphylococcus aureus at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID645482Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess method2012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
Microbial transformation of deoxyandrographolide and their inhibitory activity on LPS-induced NO production in RAW 264.7 macrophages.
AID776248Antidyslipidemic activity in Charles foster rat assessed as increase in triton WR-1339-reduced post heparin lipolytic activity level in plasma at 100 mg/kg, po after 18 hrs by spectrophotometric analysis relative to triton-treated rat2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
AID1204065Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation on cytotoxic activities.
AID1544504Induction of neurite outgrowth in NGF-induced rat PC12 cells assessed as neurite bearing cells at 20 uM cotreated with 20 ng/ml NGF incubated for 48 hrs by light microscopy2019Bioorganic & medicinal chemistry, 06-01, Volume: 27, Issue:11
Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.
AID776250Antidyslipidemic activity in Charles foster rat assessed as decrease in triton WR-1339-induced phospholipid level in plasma at 100 mg/kg, po after 18 hrs relative to triton-treated rat2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
AID380106Antimicrobial activity against Aspergillus niger at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID1408139Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of alpha-SMA mRNA level at 500 nM measured after 24 hrs by qRT-PCR method2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID249075Concentration causing 50% inhibition of cancer cell growth against human colon SW620 cell line2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.
AID380104Antimicrobial activity against Candida albicans at 10 ug/ml by disk diffusion assay2006Journal of natural products, Mar, Volume: 69, Issue:3
ent-Labdane diterpenoids from Andrographis paniculata.
AID1408140Antifibrotic activity against mouse NIH/3T3 cells assessed as inhibition of FN mRNA level at 500 nM measured after 24 hrs by qRT-PCR method2018European journal of medicinal chemistry, Sep-05, Volume: 157Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.
AID1544493Antiinflammatory activity in mouse BV2 cells assessed as reduction in LPS-induced NO production at 20 uM incubated for 24 hrs by Griess method2019Bioorganic & medicinal chemistry, 06-01, Volume: 27, Issue:11
Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.
AID383495Antiproliferative activity against human HL60 cells by trypan blue assay2008Journal of natural products, May, Volume: 71, Issue:5
ent-Labdane diterpenoid lactone stereoisomers from Andrographis paniculata.
AID776249Antidyslipidemic activity in Charles foster rat assessed as decrease in triton WR-1339-induced triglyceride level in plasma at 100 mg/kg, po after 18 hrs relative to triton-treated rat2013European journal of medicinal chemistry, Nov, Volume: 69Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (30)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (6.67)18.2507
2000's8 (26.67)29.6817
2010's17 (56.67)24.3611
2020's3 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.74

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.74 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index5.13 (4.65)
Search Engine Demand Index27.14 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.74)

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%
Other30 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]