Neoamygdalin

Details

• Internal ID: d6c4b1ac-b3d6-4dfd-a1eb-8cf6e4efd56a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: (2S)-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
• SMILES (Canonical): C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
• 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-/m1/s1
• InChI Key: XUCIJNAGGSZNQT-UUGBRMIUSA-N
• Popularity: 653 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

• 29883-16-7
• L-Amylgdalin
• (S)-Amylgdalin
• Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (S)-
• amygdalin
• Benzeneacetonitrile, alpha-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-, (alphaS)-
• (S)-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
• C20-H27-N-O11
• L-AMYGDALIN
• DTXSID701318081
• AKOS040753237
• NCGC00385265-01
• (2S)-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
• MS-28344
• HY-121376
• CS-0081824
• E88599
• NCGC00385265-01_C20H27NO11_(2S)-{[6-O-(beta-D-Glucopyranosyl)-beta-D-glucopyranosyl]oxy}(phenyl)acetonitrile

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

• Achillea lycaonica
• Aconitum maximum
• Aconitum vilmorinianum
• Actinidia kolomikta
• Albizia gummifera
• Boronia koniambiensis
• Canarium strictum
• Citrus maxima
• Coreopsis grandiflora
• Dipteronia dyeriana
• Dodonaea polyandra
• Garcinia macrophylla
• Gymnanthemum amygdalinum
• Gymnosporia serrata
• Maytenus loeseneri
• Murraya kwangsiensis
• Odontites vulgaris
• Ongokea gore
• Ophiorrhiza blumeana
• Passiflora edulis
• Peucedanum palustre
• Phalaenopsis aphrodite
• Physalis solanaceus
• Plectranthus mollis
• Podocarpus salignus
• Prosopis ruscifolia
• Prunus armeniaca
• Prunus davidiana
• Prunus mandshurica
• Prunus persica
• Prunus serotina
• Prunus sibirica
• Psychotria bahiensis
• Schistostephium rotundifolium
• Sideritis syriaca
• Siphocampylus verticillatus
• Vepris pilosa
• Veratrum shanense
• Viburnum chingii
• Zanthoxylum melanostictum

Cross-Links

• PubChem: 441462
• NPASS: NPC94346
• LOTUS: LTS0185608
• wikiData: Q105342110