Page last updated: 2024-12-11

narcissin flavonol

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Description

narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM)) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Strumpfiagenus[no description available]RubiaceaeThe Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]

Cross-References

ID SourceID
PubMed CID5481663
CHEMBL ID258394
CHEBI ID145096
SCHEMBL ID7167500
MeSH IDM0097883

Synonyms (53)

Synonym
604-80-8
5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-1-benzopyran-4-one
isorhamnetin-3-o-rutinoside
isorhamnetin 3-o-rutinoside
4h-1-benzopyran-4-one, 3-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
4h-benzopyran-4-one, 3-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
isorhamnetin 3-rhamnoglucoside
narcissin
isorhamnetin 3-rutinoside
narcissoside
C16060
narcissin flavonol
CHEMBL258394
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
CHEBI:145096
SCHEMBL7167500
unii-n4ax11l1tf
n4ax11l1tf ,
S9423
bdbm50379284
c28h32o16
isorhamnetin-3-o-rutinoside (constituent of ginkgo) [dsc]
isorhamnetin 3-o-.beta.-d-(6-o-.alpha.-l-rhamnosyl)glucoside
isorhamnetin 3-o-.beta.-rutinoside
isorhamnetin-3-o-rutinoside [usp-rs]
4h-1-benzopyran-4-one, 3-996-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
3'-o-methylquercetin 3-rutinoside
isorhamentin-3-o-.beta.-d-rutinoside
3-o-rutinosylisorhamnetin
isorhamnetin 3-.beta.-o-rutinoside
AC-34730
isorhamnetin-3-rutinoside
isprhamnetin-3-rutinoside
DTXSID00209157 ,
mfcd00017734
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4h-chromen-4-one
AS-75139
AKOS030632878
HY-N0649
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)methyl)tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one
Q23418564
4h-1-benzopyran-4-one,3-[[6-o-(6-deoxy-a-l-mannopyranosyl)-b-d-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
CCG-270266
CS-0009675
isorhamnetin3-rutinoside
dtxcid20131648
isorhamnetin 3-o-beta-rutinoside
isorhamnetin 3-beta-o-rutinoside
isorhamnetin-3-o-rutinoside (usp-rs)
4h-1-benzopyran-4-one, 3-996-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
isorhamnetin-3-o-rutinoside (constituent of ginkgo)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
disaccharide derivativeA carbohydrate derivative that is formally obtained from a disaccharide.
glycosyloxyflavoneA member of the class of flavones having one or more glycosyl residues attached at unspecified positions.
monomethoxyflavoneAny methoxyflavone with a single methoxy substituent.
trihydroxyflavoneAny hydroxyflavone carrying three hydroxy groups at unspecified positions.
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC50 (µMol)12.10000.00041.877310.0000AID654333
Cytochrome P450 3A4Homo sapiens (human)IC50 (µMol)80.00000.00011.753610.0000AID380506
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID377830Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins2005Journal of natural products, Apr, Volume: 68, Issue:4
Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.
AID654332Inhibition of advanced glycation end-products formation after 14 days by spectrofluorimetry2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities.
AID377832Antioxidant activity assessed as 3-morpholinosydnonimine-derived peroxynitrite free radical scavenging activity after 30 mins2005Journal of natural products, Apr, Volume: 68, Issue:4
Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.
AID1316657Antineuroinflammatory activity in human BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Bioactive phenols as potential neuroinflammation inhibitors from the leaves of Xanthoceras sorbifolia Bunge.
AID379568Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 10 molar ratio relative to TPA2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID1434704Antineuroinflammatory activity in mouse N9 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap.
AID517389Inhibition of AMPK-mediated adipocyte differentiation in mouse 3T3L1 cells2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
The selected flavonol glycoside derived from Sophorae Flos improves glucose uptake and inhibits adipocyte differentiation via activation AMPK in 3T3-L1 cells.
AID642414Estrogenic activity at ERalpha in human MVLN cells at 100 ug/mL after 24 hrs by luciferase reporter gene assay relative to E22012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID1193988Inhibition of LPS-induced IL-12 p40 production in wild-type C57BL/6 mouse BMDC pretreated with compound for 1 hr before LPS treatment measured 16 hrs by ELISA2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs).
AID1193518Inhibition of Streptococcus mutans OMZ65 sortase A lacking N-terminal membrane anchor domain (1 to 40 amino acids) expressed in Escherichia coli TOP10 using Dabcyl-QALPETGEE-Edans substrate incubated for 1 hr by fluorescence spectrophotometry2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Streptococcus mutans sortase A inhibitory metabolites from the flowers of Sophora japonica.
AID338974Inhibition of cow milk xanthine oxidase at 50 ug/mL
AID1316660Cytotoxicity against LPS-activated human BV2 cells assessed as cell viability at 30 uM after 24 hrs by MTT assay (Rvb = 98.03 to 98.84%)2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Bioactive phenols as potential neuroinflammation inhibitors from the leaves of Xanthoceras sorbifolia Bunge.
AID1193990Inhibition of LPS-induced TNF-alpha production in wild-type C57BL/6 mouse BMDC pretreated with compound for 1 hr before LPS treatment measured 16 hrs by ELISA2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs).
AID379565Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 1000 molar ratio relative to TPA2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID1316658Cytotoxicity against LPS-activated human BV2 cells assessed as cell viability at 1 uM after 24 hrs by MTT assay (Rvb = 98.03 to 98.84%)2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Bioactive phenols as potential neuroinflammation inhibitors from the leaves of Xanthoceras sorbifolia Bunge.
AID1193989Inhibition of LPS-induced IL-6 production in wild-type C57BL/6 mouse BMDC pretreated with compound for 1 hr before LPS treatment measured 16 hrs by ELISA2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs).
AID1654523Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability at 6.25 to 100 uM after 24 hrs by EZ-Cytox cell viability assay
AID380506Inhibition of CYP3A42006Journal of natural products, Mar, Volume: 69, Issue:3
Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.
AID1193519Toxicity against Streptococcus mutans assessed as inhibition of microbial growth2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Streptococcus mutans sortase A inhibitory metabolites from the flowers of Sophora japonica.
AID1616814Cytoprotective activity against CdCl2-induced cell death in human HEK293T cells at 25 to 100 uM preincubated for 2 hrs followed by CdCl2 treatment and measured after 12 hrs by MTT assay2019Journal of natural products, 10-25, Volume: 82, Issue:10
Constituents from the Leaves of
AID379573Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID1293873Inhibition of HDAC in mouse C127-LT cells assessed as activation of EGFP expression at 10 uM after 24 hrs by fluorescence microscopy2016Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9
Identification of new quinic acid derivatives as histone deacetylase inhibitors by fluorescence-based cellular assay.
AID379569Inhibition of TPA-induced EBV-early antigen activation in human Raji cells relative to TPA2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID360611Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS trophozoites after 48 hrs by MTT/PMS assay2001Journal of natural products, May, Volume: 64, Issue:5
Antiprotozoal activity of the constituents of Conyza filaginoides.
AID379572Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID1316661Cytotoxicity against LPS-activated human BV2 cells assessed as cell viability at 100 uM after 24 hrs by MTT assay (Rvb = 98.03 to 98.84%)2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Bioactive phenols as potential neuroinflammation inhibitors from the leaves of Xanthoceras sorbifolia Bunge.
AID294158Inhibition of diphenolase activity of mushroom tyrosinase at 0.053 mM2007Bioorganic & medicinal chemistry, Apr-01, Volume: 15, Issue:7
Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum.
AID379570Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID377831Antioxidant activity assessed as authentic peroxynitrite free radical scavenging activity after 30 mins2005Journal of natural products, Apr, Volume: 68, Issue:4
Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.
AID328637Vasorelaxation activity in Sprague-Dawley rat aortic assessed as inhibition of phenylephrin-induced contraction2008Journal of natural products, Feb, Volume: 71, Issue:2
Vasorelaxing alkaloids and flavonoids from Cassytha filiformis.
AID1316659Cytotoxicity against LPS-activated human BV2 cells assessed as cell viability at 10 uM after 24 hrs by MTT assay (Rvb = 98.03 to 98.84%)2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Bioactive phenols as potential neuroinflammation inhibitors from the leaves of Xanthoceras sorbifolia Bunge.
AID379567Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 100 molar ratio relative to TPA2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID642415Estrogenic activity at ERalpha in human MVLN cells at 20 ug/mL after 24 hrs by luciferase reporter gene assay relative to E22012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID379571Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID360612Antiprotozoal activity against Giardia lamblia IMSS:0989:1 after 48 hrs by MTT/PMS assay2001Journal of natural products, May, Volume: 64, Issue:5
Antiprotozoal activity of the constituents of Conyza filaginoides.
AID517391Cytotoxicity against mouse 3T3L1 cells at 20 uM after 24 hrs2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
The selected flavonol glycoside derived from Sophorae Flos improves glucose uptake and inhibits adipocyte differentiation via activation AMPK in 3T3-L1 cells.
AID517390Inhibition of PPAR-gamma-mediated adipocyte differentiation in mouse 3T3L1 cells2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
The selected flavonol glycoside derived from Sophorae Flos improves glucose uptake and inhibits adipocyte differentiation via activation AMPK in 3T3-L1 cells.
AID379566Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 500 molar ratio relative to TPA2006Journal of natural products, Dec, Volume: 69, Issue:12
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
AID654333Inhibition of Sprague-Dawley rat lens aldose reductase2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (36)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (5.56)18.7374
1990's2 (5.56)18.2507
2000's10 (27.78)29.6817
2010's21 (58.33)24.3611
2020's1 (2.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.55

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 Index11.55 (24.57)
Research Supply Index3.64 (2.92)
Research Growth Index5.19 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.55)

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%
Other37 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]