Amygdalin

Details

• Internal ID: a5d2a473-c2de-4529-af9e-1dffd34a3549
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: (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
• 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
• InChI Key: XUCIJNAGGSZNQT-JHSLDZJXSA-N
• Popularity: 3,360 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₇NO₁₁
• Molecular Weight: 457.40 g/mol
• Exact Mass: 457.15841068 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.11
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 29883-15-6
• (R)-Amygdalin
• D-Amygdalin
• (R)-Laenitrile
• (R)-Amygdaloside
• R-Amygdalin
• NSC-15780
• D(-)-Mandelonitrile-beta-D-gentiobioside
• D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
• 214UUQ9N0H
• NSC 15780
• Glucoprunasin
• CHEBI:17019
• DTXSID00897159
• (-)-D-mandelonitrile beta-D-gentiobioside
• (R)-alpha-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile
• Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)-
• (2R)-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy](phenyl)acetonitrile
• (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
• CHEBI:27613
• NSC251222
• (2R)-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile
• (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
• RefChem:5553
• Mandelonitrile beta Gentiobioside
• DTXCID701326581
• 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)oxy)methyl)oxan-2-yl)oxy)acetonitrile
• 249-925-3
• ((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile
• NSC15780
• Amygdaloside
• Benzeneacetonitrile,a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, (aR)-
• (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
• MFCD00006598
• C20H27NO11
• (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)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
• UNII-214UUQ9N0H
• MFCD00866428
• HSDB 3559
• EINECS 249-925-3
• BRN 0066856
• Amygdalin/Vitamin B17
• AMYGDALIN [MI]
• AMYGDALIN [HSDB]
• bmse000139
• AMYGDALIN [WHO-DD]
• 5-17-08-00118 (Beilstein Handbook Reference)
• MLS002473175
• SCHEMBL131406
• CHEMBL461727
• orb1305010
• MSK1532
• HMS2205O07
• HY-N0190
• s2260
• AKOS016034288
• CCG-269308
• CS-6162
• DS-7377
• SMP1_000103
• AC-27315
• SMR001397267
• SY067870
• D-(-)-mandelonitrile-beta-D-gentiobioside
• NS00015336
• C08325
• Q410215
• BRD-K03504028-001-07-6
• (2R)-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)(PHENYL)ACETONITRILE
• (R)-alpha-((6-O-beta-D-glucopyranosyl-beta-D- glucopyranosyl)oxy)benzeneacetonitrile
• (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto
• Benzeneacetonitrile, alpha-[(6-O-.beta.-D-glucopyransoyl-.beta.-D-glucopyranosyl)oxy]-, (R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9659	96.59%
Caco-2	-	0.8852	88.52%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6381	63.81%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9522	95.22%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8294	82.94%
P-glycoprotein inhibitior	-	0.7635	76.35%
P-glycoprotein substrate	-	0.9460	94.60%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8151	81.51%
CYP3A4 inhibition	-	0.9010	90.10%
CYP2C9 inhibition	-	0.8779	87.79%
CYP2C19 inhibition	-	0.8557	85.57%
CYP2D6 inhibition	-	0.9039	90.39%
CYP1A2 inhibition	-	0.9060	90.60%
CYP2C8 inhibition	-	0.7738	77.38%
CYP inhibitory promiscuity	-	0.7513	75.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6796	67.96%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9574	95.74%
Skin irritation	-	0.8639	86.39%
Skin corrosion	-	0.9677	96.77%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8155	81.55%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9070	90.70%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.7381	73.81%
Acute Oral Toxicity (c)	II	0.7430	74.30%
Estrogen receptor binding	+	0.6173	61.73%
Androgen receptor binding	-	0.6085	60.85%
Thyroid receptor binding	+	0.5690	56.90%
Glucocorticoid receptor binding	-	0.6130	61.30%
Aromatase binding	+	0.7052	70.52%
PPAR gamma	+	0.7089	70.89%
Honey bee toxicity	-	0.5782	57.82%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.8745	87.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.86%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.46%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.59%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.73%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	90.93%	95.93%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	89.10%	94.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.00%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	87.68%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.98%	94.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.46%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.90%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.43%	86.92%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.23%	95.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.12%	83.00%

Plants that contains it

• Aconitum maximum
• Aconitum vilmorinianum
• Actinidia kolomikta
• Bergera kwangsiensis
• Boronia koniambiensis
• Canarium strictum
• Coreopsis grandiflora
• Dipteronia dyeriana
• Dodonaea polyandra
• Equilabium molle
• Garcinia cowa
• Garcinia macrophylla
• Gerbera jamesonii
• Gymnanthemum amygdalinum
• Gymnosporia serrata
• Maytenus loeseneri
• Neltuma ruscifolia
• Odontites vulgaris
• Ongokea gore
• Ophiorrhiza blumeana
• Oxyanthus pyriformis
• Passiflora edulis
• Peucedanum palustre
• Phalaenopsis aphrodite
• Physalis solanaceus
• Podocarpus salignus
• Prunus armeniaca
• Prunus cerasus
• Prunus davidiana
• Prunus domestica
• Prunus humilis
• Prunus japonica
• Prunus mandshurica
• Prunus persica
• Prunus salicina
• Prunus serotina
• Prunus sibirica
• Prunus spinosa
• Pseudocydonia sinensis
• Psychotria bahiensis
• Rumex dentatus
• Schistostephium rotundifolium
• Sideritis syriaca
• Siphocampylus verticillatus
• Vepris glomerata var. glomerata
• Veratrum shanense
• Viburnum chingii
• Zanthoxylum melanostictum

Cross-Links

• PubChem: 656516
• NPASS: NPC266389
• LOTUS: LTS0251059
• wikiData: Q410215