Molecule

(R)-amygdalin

AlkaPlorer ID: AK003501

Synonym: '', '(R)-Amygdalin', 'D(-)-Mandelonitrile-.beta.-D-gentiobioside', '(-)-D-mandelonitrile beta-D-gentiobioside', 'Mandelonitrile-.beta.-gentiobioside', 'D-amygdalin', 'Benzeneacetonitrile, .alpha.-(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy-, (R)-', 'D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside', '(R)-Laenitrile', 'Mandelonitrile ?-gentiobioside', 'AMYGDALIN', 'Benzeneacetonitrile, .alpha.-((6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy)-, (R)-', 'D-(-)-mandelonitrile-beta-D-gentiobioside', '(R)-Amygdaloside', '(R)-amygdalin', 'Amygdaloside', 'D-Amygdalin', 'Amygdalin'

IUPAC Name: (2R)-2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile

Structure

SMILES: N#C[C@H](OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C1=CC=CC=C1

InChI: InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11?,12?,13?,14?,15?,16?,17?,18?,19?,20?/m0/s1

InChIKey: XUCIJNAGGSZNQT-VEXRWARGSA-N

Reference

Tissue Level Compartmentation of (R)-Amygdalin and Amygdalin Hydrolase Prevents Large-Scale Cyanogenesis in Undamaged Prunus Seeds

PubChem CID: 656495

CAS: 29883-15-6

LOTUS: LTS0253111

NPASS: NPC216605

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Prunus humilis	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus mandshurica	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus persica	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus sibirica	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus davidiana	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus japonica	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus pedunculata	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus armeniaca	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 457.4320000000001

TPSA？: 202.32

MolLogP？: -3.108019999999997

Number of H-Donors: 7

Number of H-Acceptors: 12

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Acinetobacter baumannii	Acinetobacter baumannii	MIC	10000.0	nM	10.6019/CHEMBL4296183
Candida albicans	Candida albicans	MIC	10000.0	nM	10.6019/CHEMBL4296183
Cryptococcus neoformans	Cryptococcus neoformans	MIC	10000.0	nM	10.6019/CHEMBL4296183
Escherichia coli	Escherichia coli	MIC	10000.0	nM	10.6019/CHEMBL4296183
Homo sapiens	A498	GI50	11614.49	nM	None
Homo sapiens	A549	GI50	250034.54	nM	None
Homo sapiens	CAKI-1	GI50	250034.54	nM	None
Homo sapiens	CCRF-CEM	GI50	250034.54	nM	None
Homo sapiens	COLO 205	GI50	250034.54	nM	None
Homo sapiens	DLD-1	GI50	250034.54	nM	None
Homo sapiens	DMS-114	GI50	250034.54	nM	None
Homo sapiens	DMS-273	GI50	250034.54	nM	None
Homo sapiens	EKVX	GI50	250034.54	nM	None
Homo sapiens	HCC 2998	GI50	250034.54	nM	None
Homo sapiens	HCT-116	GI50	250034.54	nM	None
Homo sapiens	HCT-15	GI50	250034.54	nM	None
Homo sapiens	HEK293	CC50	10000.0	nM	10.6019/CHEMBL4296183
Homo sapiens	HL-60	GI50	157761.13	nM	None
Homo sapiens	HOP-18	GI50	250034.54	nM	None
Homo sapiens	HOP-62	GI50	250034.54	nM	None
Homo sapiens	HOP-92	GI50	2500.35	nM	None
Homo sapiens	HT-29	GI50	250034.54	nM	None
Homo sapiens	IGROV-1	GI50	250034.54	nM	None
Homo sapiens	K562	GI50	250034.54	nM	None
Homo sapiens	KM12	GI50	250034.54	nM	None
Homo sapiens	KM-20L2	GI50	250034.54	nM	None
Homo sapiens	LOX IMVI	GI50	195433.95	nM	None
Homo sapiens	M19-MEL	GI50	250034.54	nM	None
Homo sapiens	Malme-3M	GI50	250034.54	nM	None
Homo sapiens	MCF7	GI50	250034.54	nM	None
Homo sapiens	MOLT-4	GI50	157761.13	nM	None
Homo sapiens	NCI/ADR-RES	GI50	250034.54	nM	None
Homo sapiens	NCI-H226	GI50	191425.59	nM	None
Homo sapiens	NCI-H23	GI50	250034.54	nM	None
Homo sapiens	NCI-H322M	GI50	250034.54	nM	None
Homo sapiens	NCI-H460	GI50	250034.54	nM	None
Homo sapiens	NCI-H522	GI50	200447.2	nM	None
Homo sapiens	OVCAR-3	GI50	250034.54	nM	None
Homo sapiens	OVCAR-4	GI50	250034.54	nM	None
Homo sapiens	OVCAR-5	GI50	250034.54	nM	None
Homo sapiens	OVCAR-8	GI50	250034.54	nM	None
Homo sapiens	RPMI-8226	GI50	250034.54	nM	None
Homo sapiens	RXF 393	GI50	250034.54	nM	None
Homo sapiens	SF-268	GI50	250034.54	nM	None
Homo sapiens	SF-295	GI50	202768.27	nM	None
Homo sapiens	SF-539	GI50	214289.06	nM	None
Homo sapiens	SK-MEL-2	GI50	250034.54	nM	None
Homo sapiens	SK-MEL-28	GI50	250034.54	nM	None
Homo sapiens	SK-MEL-5	GI50	250034.54	nM	None
Homo sapiens	SK-OV-3	GI50	250034.54	nM	None
Homo sapiens	SN12C	GI50	250034.54	nM	None
Homo sapiens	SN12K1	GI50	250034.54	nM	None
Homo sapiens	SNB-19	GI50	250034.54	nM	None
Homo sapiens	SNB-75	GI50	250034.54	nM	None
Homo sapiens	SNB-78	GI50	227509.74	nM	None
Homo sapiens	SW-620	GI50	250034.54	nM	None
Homo sapiens	U-251	GI50	250034.54	nM	None
Homo sapiens	UACC-257	GI50	234422.88	nM	None
Homo sapiens	UACC-62	GI50	247172.41	nM	None
Homo sapiens	UO-31	GI50	250034.54	nM	None
Homo sapiens	XF498	GI50	23442.29	nM	None
Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	10000.0	nM	10.6019/CHEMBL4296183
Mus musculus	P388	GI50	231739.46	nM	None
Mus musculus	P388/ADR	GI50	170215.85	nM	None
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	10000.0	nM	10.6019/CHEMBL4296183
Staphylococcus aureus	Staphylococcus aureus	MIC	10000.0	nM	10.6019/CHEMBL4296183