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Amygdalin

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Cyanogenic Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H](c3ccccc3)C#N)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)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+/m0/s1
InChIKey	XUCIJNAGGSZNQT-JHSLDZJXSA-N
Formula	C₂₀H₂₇NO₁₁
HBA	12
HBD	7
MW	457.43
Rotatable Bonds	7
TPSA	202.32
LogP	-3.11
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.65
Exact Mass	457.16
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Iochroma cyaneum	Convolvulaceae	Plantae	362357
2	Merremia dissecta	Convolvulaceae	Plantae	197414
3	Prunus persica	Rosaceae	Plantae	3760

Showing of synonyms

Elshamy A.I, Abdallah H.M.I, et al. (2019). Evaluation of Anti-inflammatory, Antinociceptive, and Antipyretic Activities of Prunus persica var nucipersica (Nectarine) Kernel. Planta medica,2019, 85(11-12), 1016-1023. [View] [PubMed]
Sattar EA, Glasl H, et al. (1990). Hydroxycinnamic acid amides from Iochroma cyaneum. Phytochemistry,1990,29(12),3931-3933. [View]

Pubchem: 656516

Cas: 29883-15-6

Gnps: CCMSLIB00006492306

Zinc: ZINC000008214484

Chebi: 17019

Nmrshiftdb2: 40265325

Metabolights: MTBLC17019

Chembl: CHEMBL461727

Comptox: DTXSID00897159

Selleck: Amygdalin

CPRiL: 40587

SMILES: c1ccccc1COC(O2)CCCC2COC3CCCCO3

Level: 2

Mol. Weight: 457.43 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 457.43 g/mol

SMILES: c1ccccc1COC2CCCCO2

Level: 1

Mol. Weight: 457.43 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 457.43 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 457.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.13
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.250
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.28

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.770
Plasma Protein Binding: 69.0
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.310
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.580
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.950
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.370
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -74.750
Rat (Acute): 2.710
Rat (Chronic Oral): 3.740
Fathead Minnow: 3.340
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 500.590
Hydration Free Energy: -4.720
Log(D) at pH=7.4: -0.900
Log(P): -2.32
Log S: -1.76
Log(Vapor Pressure): -17.06
Melting Point: 157.51
pKa Acid: 3.63
pKa Basic: 5.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8701
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8509
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8475
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8260
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7853
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7752
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7629
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7583
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7550
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7508
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7473
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7464
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7443
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7391
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7389
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7346
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7314
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7295
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7291
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7255
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7158
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7126
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7119
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7107
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7075
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7018
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7005

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