Page last updated: 2024-11-04

amygdalin

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

Description

(R)-amygdalin : An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration. [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]

Cross-References

ID SourceID
PubMed CID2180
CHEMBL ID1967951
SCHEMBL ID13387202
MeSH IDM0001043
PubMed CID34751
CHEMBL ID515712
CHEBI ID27613
SCHEMBL ID131407
MeSH IDM0001043
PubMed CID656495
CHEMBL ID2007233
MeSH IDM0001043
PubMed CID656516
CHEMBL ID461727
CHEBI ID17019
SCHEMBL ID131406
MeSH IDM0001043

Synonyms (150)

Synonym
LS-14805
benzeneacetonitrile, .alpha.-[(6-o-.beta.-d-glucopyranosyl-.beta.-d-gluco-pyranosyl)oxy]-
amygdalin,(dl)
nsc-251222
benzeneacetonitrile, .alpha.-[(6-o-.beta.-d-glucopyranosyl-.beta.-d-glucopyranosyl)oxy]-
NCI60_002005
isoamygdalin
2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
2-phenyl-2-(3,4,5-trihydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)(2h-3,4,5,6 -tetrahydropyran-2-yloxy)]methyl}(2h-3,4,5,6-tetrahydropyran-2-yloxy))ethaneni trile
HMS3341N01
SCHEMBL13387202
AKOS024282419
CHEMBL1967951
2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
benzeneacetonitrile, .alpha.-[(6-o-.beta.-d-glucopyranosyl-.beta.-d-glucopyranosyl)oxy]-, (r)-
XUCIJNAGGSZNQT-UHFFFAOYSA-N
[(6-o-hexopyranosylhexopyranosyl)oxy](phenyl)acetonitrile #
benzeneacetonitrile,a-[(6-o-b-d-glucopyranosyl-b-d-glucopyranosyl)oxy]-
HMS3655P16
glucoprunasin
NCGC00380662-01
DTXSID20872004
1173199-73-9
alpha-[(6-o-hexopyranosylhexopyranosyl)oxy]benzeneacetonitrile
gtpl12451
d-(-)-amygdalin
benzeneacetonitrile, .
amygdalin(d)
d(-)-amygdalin
BRD-A59552297-001-02-5
dl-amygdalin
DIVK1C_000106
KBIO1_000106
[(6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy](phenyl)acetonitrile
SDCCGMLS-0066722.P001
mandelonitrile-beta-gentiobioside
CHEBI:27613 ,
vitamin b17
SPECTRUM_001192
SPECTRUM4_001750
IDI1_000106
NCGC00178377-01
benzeneacetonitrile, alpha-[(6-o-.beta.-d-glucopyransoyl-.beta.-d-glucopyranosyl)oxy]-, (rs)-
NSC251222 ,
2-phenyl-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
BSPBIO_002948
SPECTRUM5_000580
amygdalin, from apricot kernels, >=99%
KBIOGR_002200
KBIO3_002448
KBIO2_004240
KBIO2_006808
KBIO2_001672
KBIOSS_001672
SPBIO_000748
SPECTRUM2_000904
NINDS_000106
SPECTRUM3_001534
SPECTRUM1502244
amygdalin, bioxtra, >=97.0% (hplc)
A0443
2-phenyl-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
HMS500F08
CHEMBL515712
HMS1921N18
96420-61-0
CCG-39554
SCHEMBL131407
mfcd00866428
d-amygdalin hydrate
2-phenyl-2-(((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)acetonitrile
SR-05000002154-2
sr-05000002154
6-o-beta-d-glucosido-beta-d-glucoside
2-phenyl-2-((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)methyl)tetrahydro-2h-pyran-2-yloxy)acetonitrile
AKOS032949559
d(-)-amygdalin hydrate
phillyrin,forsythin. phillyroside
amygdalin,(s)
Q27103225
AS-14698
BRD-A59552297-001-03-3
STL564520
{[6-o-(beta-d-glucopyranosyl)-beta-d-glucopyranosyl]oxy}(phenyl)acetonitrile
d-amygdalin 100 microg/ml in acetonitrile
NCGC00178377-02
DTXSID001031434
amygdaloside
mandelonitrile-.beta.-gentiobioside
d(-)-mandelonitrile-.beta.-d-gentiobioside
d-amygdalin
benzeneacetonitrile, (r)-
nsc15780 ,
amygdalin ,
NCI60_001147
CHEMBL2007233
(-)-d-mandelonitrile beta-d-gentiobioside
d-mandelonitrile-beta-d-glucosido-6-beta-d-glucoside
(2r)-[(6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy](phenyl)acetonitrile
d-(-)-mandelonitrile-beta-d-gentiobioside
CHEBI:17019 ,
d(-)-mandelonitrile-beta-d-gentiobioside
brn 0066856
nsc 15780
einecs 249-925-3
r-amygdalin
hsdb 3559
benzeneacetonitrile, alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)-, (r)-
(r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneacetonitrile
nsc-15780
SMP1_000103
(r)-laenitrile
(r)-amygdalin
(r)-amygdaloside
C08325
(r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d- glucopyranosyl)oxy)benzeneacetonitrile
MLS002473175
BMSE000139
smr001397267
CHEMBL461727
(2r)-2-phenyl-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
A820093
HMS2205O07
unii-214uuq9n0h
5-17-08-00118 (beilstein handbook reference)
214uuq9n0h ,
AKOS016034288
(2r)-((6-o-.beta.-d-glucopyranosyl-.beta.-d-glucopyranosyl)oxy)(phenyl)acetonitrile
amygdalin [hsdb]
amygdalin [mi]
amygdalin [who-dd]
S2260
SCHEMBL131406
amygdalin (vitamin b17)
XUCIJNAGGSZNQT-JHSLDZJXSA-N
(r)-2-phenyl-2-(((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)acetonitrile
AC-27315
HY-N0190
CS-6162
mandelonitrile gentiobioside
DS-7377
Q410215
benzeneacetonitrile,a-[(6-o-b-d-glucopyranosyl-b-d-glucopyranosyl)oxy]-, (ar)-
AMY33421
CCG-269308
DTXSID00897159 ,
mandelonitrile beta gentiobioside
(2r)-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)(phenyl)acetonitrile
dtxcid701326581
(r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneacetonitr ile

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" as occurs in those with Leber's Optic Atrophy) or a diet low in sulfur containing amino acids are predicted to be at increased risk to developing adverse side effects from laetrile, a cyanide containing substance used in cancer treatment."( Possible adverse side effects from treatment with laetrile.
Calabrese, EJ, 1979
)
0.26
"Individuals who have a reduced capacity to detoxify cyanide to thiocyanate are at increased risk to experience adverse side effects from laetrile, a cyanide containing substance used in cancer treatment."( Conjoint use of laetrile and megadoses of ascorbic acid in cancer treatment: possible side effects.
Calabrese, EJ, 1979
)
0.26
" When 2 concentrations of HMFG1-beta-glucosidase were compared, the toxic effect was dose dependent."( In vitro cytotoxicity following specific activation of amygdalin by beta-glucosidase conjugated to a bladder cancer-associated monoclonal antibody.
Epenetos, AA; Rowlinson-Busza, G; Syrigos, KN, 1998
)
0.3
" The adverse drug reaction was rated probable on the Naranjo probability scale."( Life-threatening interaction between complementary medicines: cyanide toxicity following ingestion of amygdalin and vitamin C.
Bromley, J; Buckley, NA; Hughes, BG; Leong, DC, 2005
)
0.33
" Safety profile was assessed by adverse events and physical examination throughout the study."( Pharmacokinetics, Safety, and Tolerability of Amygdalin and Paeoniflorin After Single and Multiple Intravenous Infusions of Huoxue-Tongluo Lyophilized Powder for Injection in Healthy Chinese Volunteers.
Ding, L; Gong, C; Jian, L; Li, X; Shi, F; Sun, C; Zhang, R, 2016
)
0.43
" No serious adverse events were observed during the entire study."( Pharmacokinetics, Safety, and Tolerability of Amygdalin and Paeoniflorin After Single and Multiple Intravenous Infusions of Huoxue-Tongluo Lyophilized Powder for Injection in Healthy Chinese Volunteers.
Ding, L; Gong, C; Jian, L; Li, X; Shi, F; Sun, C; Zhang, R, 2016
)
0.43
"Indroduction: This article presents a theoretical analysis of the safe form and dosage of the amygdalin derivative."( Theoretical Analysis for the Safe Form and Dosage of Amygdalin Product.
Tsanov, H; Tsanov, V, 2020
)
0.56
" Unfortunately, there is currently no foolproof method for determining the microbial consortium and providing a safe oral dosage for every patient."( Amygdalin: A Review on Its Characteristics, Antioxidant Potential, Gastrointestinal Microbiota Intervention, Anticancer Therapeutic and Mechanisms, Toxicity, and Encapsulation.
Abdellatif, AAH; Algheshairy, RM; Alhomaid, RM; Aljutaily, T; Almujaydil, MS; Almutairi, AS; Alshimali, SI; Barakat, H, 2022
)
0.72

Pharmacokinetics

Amygdalin (AD) and paeoniflorin (PF) are 2 typical bioactive components in HTLPI. This accurate and specific assay produced a useful LC-MS-MS method, which was successfully applied to pharmacokinetic studies after oral administration of amygdalin to rats.

ExcerptReferenceRelevance
"To investigate pharmacokinetic parameters of peoniflorin, albiflorin and amygdaloside after administration of Guizhi Fuling capsule in beagle dogs."( [Pharmacokinetics of Guizhi Fuling capsule in Beagle dogs].
Chang, X; Lv, X; Qin, J; Sun, X; Wang, Z; Xiao, W; Zhu, K, 2011
)
0.37
"The pharmacokinetic course of peoniflorin, albiflorin and amygdaloside can be described by two-compartment model, and these components have high expose."( [Pharmacokinetics of Guizhi Fuling capsule in Beagle dogs].
Chang, X; Lv, X; Qin, J; Sun, X; Wang, Z; Xiao, W; Zhu, K, 2011
)
0.37
" This accurate and specific assay produced a useful LC-MS-MS method, which was successfully applied to pharmacokinetic studies after the oral administration of amygdalin to rats."( Determination and pharmacokinetics of amygdalin in rats by LC-MS-MS.
Han, L; Huang, XT; Li, XB; Li, YY; Liu, CH; Mi, SQ; Wang, NS; Xu, ML; Zhang, R, 2014
)
0.4
"An ultra performance liquid chromatography-mass spectrometric (UPLC-MS) method was developed to investigate the pharmacokinetic properties of ephedrine, methylephedrine, amygdalin, and glycyrrhizic acid after oral gavage of Ma Huang Tang (MHT) in Beagles."( UPLC-MS/MS determination of ephedrine, methylephedrine, amygdalin and glycyrrhizic acid in Beagle plasma and its application to a pharmacokinetic study after oral administration of Ma Huang Tang.
Fu, Q; Ma, S; Wang, J; Yan, T, 2015
)
0.42
" Amygdalin (AD) and paeoniflorin (PF) are 2 typical bioactive components in HTLPI and were selected as indicators for this pharmacokinetic study of HTLPI."( Pharmacokinetics, Safety, and Tolerability of Amygdalin and Paeoniflorin After Single and Multiple Intravenous Infusions of Huoxue-Tongluo Lyophilized Powder for Injection in Healthy Chinese Volunteers.
Ding, L; Gong, C; Jian, L; Li, X; Shi, F; Sun, C; Zhang, R, 2016
)
0.43
" Pharmacokinetic parameters of AD and PF were calculated using noncompartmental analysis."( Pharmacokinetics, Safety, and Tolerability of Amygdalin and Paeoniflorin After Single and Multiple Intravenous Infusions of Huoxue-Tongluo Lyophilized Powder for Injection in Healthy Chinese Volunteers.
Ding, L; Gong, C; Jian, L; Li, X; Shi, F; Sun, C; Zhang, R, 2016
)
0.43
" Due to the low exposure of the five main medicative ingredients (amygdalin, cinnamic acid, gallic acid, paeoniflorin and paeonol) of GZFL in human, a strategy was built to qualitatively and quantitatively identify the possible metabolites of GZFL and to describe the pharmacokinetic profiles of GZFL in human."( Integrated identification, qualification and quantification strategy for pharmacokinetic profile study of Guizhi Fuling capsule in healthy volunteers.
Aa, JY; Gu, SY; Jin, XL; Ou-Yang, BC; Peng, Y; Sun, JG; Wang, GJ; Wang, Y; Wang, ZZ; Xiao, W; Zhang, KR; Zhong, YX, 2016
)
0.43
"In BYHWI, five candidate Q-marker pharmacokinetic profiles were singly fixed to two compartmental models in rat using classical compartmental analysis, but there were tremendous differences among which the candidate parameters were fluctuated from nearly 3552 folds to equivalency."( Application of TQSM polypharmacokinetics and its similarity approach to ascertain Q-marker by analyses of transitivity in vivo of five candidates in Buyanghuanwu injection.
Deng, KW; He, FY; Liao, Q; Liu, WL; Tang, Y; Xiao, MF; Yang, YT; Zhang, YT; Zhou, YQ, 2018
)
0.48
" It is feasible for Q-marker in CMMs to screen on the comparison of single pharmacokinetic behavior and bioavailability to the total quanta."( Application of TQSM polypharmacokinetics and its similarity approach to ascertain Q-marker by analyses of transitivity in vivo of five candidates in Buyanghuanwu injection.
Deng, KW; He, FY; Liao, Q; Liu, WL; Tang, Y; Xiao, MF; Yang, YT; Zhang, YT; Zhou, YQ, 2018
)
0.48

Compound-Compound Interactions

Amygdalin MF was evaluated alone and in combination with an activating agent, beta-glucosidase, against three transplantable rodent tumors. The tumors were Ridgway osteogenic sarcoma, Lewis lung carcinoma, and P388 leukemia.

ExcerptReferenceRelevance
"Amygdalin MF was evaluated alone and in combination with an activating agent, beta-glucosidase, against three transplantable rodent tumors; Ridgway osteogenic sarcoma, Lewis lung carcinoma, and P388 leukemia."( Experimental studies of the antitumor activity of amygdalin MF (NSC-15780) alone and in combination with beta-glucosidase (NSC-128056).
Laster, WR; Schabel, FM,
)
0.13
"A simple, rapid and reliable microwave-assisted extraction (MAE) combined with ultra performance liquid chromatography tandem mass spectrometry method was developed for simultaneous determination of the seven bioactive constituents in Guizhi Fuling capsule (GFC), namely gallic acid, amygdalin, albiflorin, paeoniflorin, paeonol, cinnamic acid and pachymic acid, respectively."( Simultaneous determination of seven bioactive components in Guizhi Fuling capsule by microwave-assisted extraction combined with ultra performance liquid chromatography tandem mass spectrometry.
Sui, Y; Wang, ZZ; Xiao, W; Xiong, ZL; Zhao, LS; Zhao, YT, 2016
)
0.43
" granatum and amygdalin extracts +cobalamin (group B), plus its combination with albendazole (group C)."( Punica granatum and amygdalin extracts plus cobalamin combined with albendazole reduce larval burden and myositis in experimental trichinosis.
Abdel-Aal, AA; Afife, AA; Badawi, MAM; Elmallawany, MA; Esmat, M; Fahmy, MA; Magdy, M; Shafi, IRA; Shalaby, MA, 2021
)
0.62

Bioavailability

The oral bioavailability of prunasin is approximately 50%, whereas amygdalin is hardly absorbed unchanged. MX administration improved theBioavailability of Amygdalin and Prunasin.

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
" The oral bioavailability of prunasin is approximately 50%, whereas amygdalin is hardly absorbed unchanged."( The pharmacokinetics of prunasin, a metabolite of amygdalin.
Olling, M; Rauws, AG; Timmerman, A, 1982
)
0.26
" MX administration improved the bioavailability of amygdalin and prunasin."( Concurrent quantification and comparative pharmacokinetic analysis of bioactive compounds in the Herba Ephedrae-Semen Armeniacae Amarum herb pair.
Chen, F; Luo, J; Ma, Q; Ren, M; Song, S; Tang, Q; Xie, Y; Xing, X, 2015
)
0.42
" The Q-marker was ascertained with transitive similarity and bioavailability in polypharmacokinetics."( Application of TQSM polypharmacokinetics and its similarity approach to ascertain Q-marker by analyses of transitivity in vivo of five candidates in Buyanghuanwu injection.
Deng, KW; He, FY; Liao, Q; Liu, WL; Tang, Y; Xiao, MF; Yang, YT; Zhang, YT; Zhou, YQ, 2018
)
0.48
"The results represented that the optimum Q-marker in BYHWI is astragaloside Ⅳ, whose transitivity in vivo similarity was close to the behavior of polypharmacokinetics with maximum bioavailability to the total quanta."( Application of TQSM polypharmacokinetics and its similarity approach to ascertain Q-marker by analyses of transitivity in vivo of five candidates in Buyanghuanwu injection.
Deng, KW; He, FY; Liao, Q; Liu, WL; Tang, Y; Xiao, MF; Yang, YT; Zhang, YT; Zhou, YQ, 2018
)
0.48

Dosage Studied

Amygdalin MF alone did not demonstrate significant antitumor activity against any of the three tumor systems. Blood cyanide concentrations following amygdalin treatment reached their highest level (130 nmol/ml) 1 hr after dosing and remained elevated until 3 hr after treatment.

ExcerptRelevanceReference
" Moreover, combined administration of glucose, amygdalin and beta-glucosidase evoked a significant cancerostatic effect hypogenesis, tumour regression) being comparable with the action of an Ifosfamid dosage of 150 mg-kg-1."( [Tumour hyperacidulation through intravenous glucose infusion enhanced by amygdalin and beta-glucosidase application (author's transl)].
Ardenne, M; Reitnauer, PG, 1975
)
0.25
" Routine physical and biologic tests were also performed to evaluate the manufacturing quality of both dosage forms."( Pharmaceutical assessment of amygdalin (Laetrile) products.
Davignon, JP; Kleinman, LM; Trissel, LA, 1978
)
0.26
" In dose-response studies up to the LD20 in normal mice, amygdalin MF alone did not demonstrate significant antitumor activity against any of these three tumor systems."( Experimental studies of the antitumor activity of amygdalin MF (NSC-15780) alone and in combination with beta-glucosidase (NSC-128056).
Laster, WR; Schabel, FM,
)
0.13
"4% of the dose) was excreted as intact amygdalin when the dosage was increased to 600 mg/kg BW."( On the metabolism of amygdalin. 1. The LD50 and biochemical changes in rats.
Adewusi, SR; Oke, OL, 1985
)
0.27
" Blood cyanide concentrations following amygdalin treatment reached their highest level (130 nmol/ml) 1 hr after dosing and remained elevated until 3 hr after treatment."( Comparative metabolism of linamarin and amygdalin in hamsters.
Frakes, RA; Sharma, RP; Willhite, CC, 1986
)
0.27
" These results provide a meaningful basis for developing a clinical dosage regimen in the treatment of hepatic fibrosis by FZHY."( Comparative pharmacokinetic and tissue distribution profiles of four major bioactive components in normal and hepatic fibrosis rats after oral administration of Fuzheng Huayu recipe.
Liu, CH; Liu, S; Tao, YY; Wang, CH; Yang, T; Zhou, H, 2015
)
0.42
"Indroduction: This article presents a theoretical analysis of the safe form and dosage of the amygdalin derivative."( Theoretical Analysis for the Safe Form and Dosage of Amygdalin Product.
Tsanov, H; Tsanov, V, 2020
)
0.56
" The article also presents a theoretical comparative analysis of biochemical reactivity in in vivo and in vitro media, by which we also determine the recommended dosage for patient administration."( Theoretical Analysis for the Safe Form and Dosage of Amygdalin Product.
Tsanov, H; Tsanov, V, 2020
)
0.56
"This article is a continuation of Theoretical Analysis for the Safe Form and Dosage of Amygdalin Product and Theoretical Study of the Process of Passage of Glycoside Amides through the Cell Membrane of Cancer Cell."( Theoretical Analysis of Anticancer Cellular Effects of Glycoside Amides.
Tsanov, H; Tsanov, V, 2022
)
0.72
" Unfortunately, there is currently no foolproof method for determining the microbial consortium and providing a safe oral dosage for every patient."( Amygdalin: A Review on Its Characteristics, Antioxidant Potential, Gastrointestinal Microbiota Intervention, Anticancer Therapeutic and Mechanisms, Toxicity, and Encapsulation.
Abdellatif, AAH; Algheshairy, RM; Alhomaid, RM; Aljutaily, T; Almujaydil, MS; Almutairi, AS; Alshimali, SI; Barakat, H, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role 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]

Drug Classes (4)

ClassDescription
gentiobioside
disaccharide derivativeA carbohydrate derivative that is formally obtained from a disaccharide.
cyanogenic glycosideA glycoside in which the aglycone contains a cyanide group. A cyanogenic glycoside can release poisonous hydrogen cyanide if acted upon by some enzyme.
amygdalin
[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]

Pathways (2)

PathwayProteinsCompounds
amygdalin and prunasin degradation09
prunasin and amygdalin biosynthesis015
amygdalin and prunasin degradation011
prunasin and amygdalin biosynthesis115

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Taste receptor type 2 member 16Homo sapiens (human)EC50 (µMol)20,000.00000.00490.15500.2500AID1619458; AID1619466
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
detection of chemical stimulus involved in sensory perception of bitter tasteTaste receptor type 2 member 16Homo sapiens (human)
G protein-coupled receptor signaling pathwayTaste receptor type 2 member 16Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityTaste receptor type 2 member 16Homo sapiens (human)
protein bindingTaste receptor type 2 member 16Homo sapiens (human)
bitter taste receptor activityTaste receptor type 2 member 16Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
endoplasmic reticulumTaste receptor type 2 member 16Homo sapiens (human)
trans-Golgi networkTaste receptor type 2 member 16Homo sapiens (human)
plasma membraneTaste receptor type 2 member 16Homo sapiens (human)
external side of plasma membraneTaste receptor type 2 member 16Homo sapiens (human)
membraneTaste receptor type 2 member 16Homo sapiens (human)
membraneTaste receptor type 2 member 16Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (56)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1347411qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID409942Inhibition of human recombinant MAOA by fluorimetric method2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID409943Inhibition of human recombinant MAOB by fluorimetric method2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
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.
AID1224817Assays to identify small molecules inhibitory for eIF4E expression2015Chemistry & biology, Jul-23, Volume: 22, Issue:7
Internal Ribosome Entry Site-Based Bicistronic In Situ Reporter Assays for Discovery of Transcription-Targeted Lead Compounds.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
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.
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.
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.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1628029Inhibition of rat small intestinal sucrase using sucrose as substrate assessed as amount of liberated glucose at 1 mM after 30 mins by glucose oxidase method2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Rat intestinal sucrase inhibited by minor constituents from the leaves and twigs of Archidendron clypearia (Jack.) Nielsen.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
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.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID252881Chemotactic activity of compound measured as function of concentration of 10 uM compared to peptide T,[DA1a]peptide T and amygdalin2005Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5
Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID567091Drug absorption in human assessed as human intestinal absorption rate2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Prediction of drug intestinal absorption by new linear and non-linear QSPR.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (646)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990343 (53.10)18.7374
1990's33 (5.11)18.2507
2000's52 (8.05)29.6817
2010's134 (20.74)24.3611
2020's84 (13.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Trials22 (3.32%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Reviews37 (5.58%)6.00%
Reviews1 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Case Studies39 (5.88%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other5 (100.00%)84.16%
Other565 (85.22%)84.16%
Other12 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]