Salicin

Details

• Internal ID: f2f112ea-6380-45c5-85ca-ca78b5713d3a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• InChI: InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
• InChI Key: NGFMICBWJRZIBI-UJPOAAIJSA-N
• Popularity: 4,725 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈O₇
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.10525291 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.64
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 138-52-3
• Salicoside
• D-(-)-Salicin
• Salicyl alcohol glucoside
• D(-)-Salicin
• 2-(Hydroxymethyl)phenyl beta-D-glucopyranoside
• Saligenin beta-D-glucopyranoside
• 2-(Hydroxymethyl)phenyl-beta-d-glucopyranoside
• Salicinum
• o-(Hydroxymethyl)phenyl beta-D-glucopyranoside
• CHEBI:17814
• DTXSID10883326
• NSC-5751
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• 4649620TBZ
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)oxane-3,4,5-triol
• RefChem:884384
• DTXCID901022864
• Salicine
• D-Salicin
• (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol
• MFCD00006590
• Saligenin-beta-D-glucopyranoside
• C13H18O7
• alpha-Hydroxy-o-tolyl beta-D-glucopyranoside
• Benzyl alcohol, o-hydroxy-, o-glucoside
• AI3-19099
• SPECTRUM1502255
• B-D-Glucopyranoside, 2-(hydroxymethyl)phenyl
• D-()-Salicin
• SDCCGMLS-0066698.P001
• NCGC00142605-01
• NSC 5751
• (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)-phenoxy)tetrahydro-2H-pyran-3,4,5-triol
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]tetrahydropyran-3,4,5-triol
• (2S,4S,5S,3R,6R)-6-(hydroxymethyl)-2-[2-(hydroxymethyl)phenoxy]-2H-3,4,5,6-tet rahydropyran-3,4,5-triol
• SMR000112301
• Salicin [USP]
• SR-05000001594
• Salicin (6CI,8CI)
• EINECS 205-331-6
• delta-Salicin
• UNII-4649620TBZ
• 2-(Hydroxymethyl)phenyl hexopyranoside
• SA0
• Salicin (Standard)
• Spectrum_001230
• 2-(Hydroxymethyl)phenyl-.beta.-d-glucopyranoside
• SALICIN [MI]
• SALICINUM [HPUS]
• 2-(Hydroxymethyl)phenyl b-D-glucopyranoside
• Spectrum2_000756
• Spectrum3_000948
• Spectrum4_001058
• Spectrum5_000971
• D-()-Salicin;Salicoside
• bmse000315
• D-SALICIN [USP-RS]
• SCHEMBL24936
• KBioGR_001356
• KBioSS_001710
• Saligenin-b-D-glucopyranoside
• MLS000563050
• MLS001306490
• DivK1c_000030
• S0625_SIGMA
• SPBio_000772
• CHEMBL462997
• MEGxp0_000685
• orb1310611
• Salicin (Salicoside, Salicine)
• SCHEMBL29891411
• ACon1_000373
• GTPL12454
• HMS500B12
• HY-N0149R
• KBio1_000030
• KBio2_001710
• KBio2_004278
• KBio2_006846
• KBio3_002016
• NINDS_000030
• GLXC-13826
• HMS1921P08
• HMS2092F14
• HMS2268J11
• HMS3884B15
• Pharmakon1600-01502255
• HY-N0149
• MSK40324
• Saligenin beta-delta-glucopyranoside
• Saligenin-beta-delta-glucopyranoside
• D-(-)-Salicin, analytical standard
• CCG-40332
• NSC758201
• s2351
• SBB012498
• ZINC03847505
• AKOS004907439
• AC-8042
• CS-8027
• D-(-)-Salicin, >=99% (GC)
• MS01266
• NSC-758201
• IDI1_000030
• NCGC00142605-02
• NCGC00142605-04
• ST069327
• SY038043
• SALICYL ALCOHOL GLUCOSIDE [WHO-DD]
• SBI-0051746.P002
• 2(hydroxymethyl)phenyl-beta-D-glucopyranoside
• NS00015239
• S0003
• SW219123-1
• |A-D-Glucopyranoside, 2-(hydroxymethyl)phenyl
• C01451
• 2-(Hydroxymethyl)-phenyl-beta-D-glucopyranoside
• 2-(hydroxymethyl)phenyl-O-beta-D-glucopyranoside
• AB00052296_07
• 138S523
• F212842
• Q419173
• SR-05000001594-1
• SR-05000001594-2
• BRD-K64614248-001-02-4
• BRD-K64614248-001-06-5
• BRD-K64614248-001-11-5
• BRD-K64614248-001-12-3
• EAD32BE1-198E-432C-9F44-DC0DC9A3305B
• Salicin, European Pharmacopoeia (EP) Reference Standard
• D-Salicin, United States Pharmacopeia (USP) Reference Standard
• 2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside, Salicoside, Salicyl alcohol glucoside, Saligenin beta-D-glucoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8479	84.79%
Caco-2	-	0.8059	80.59%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6134	61.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9778	97.78%
P-glycoprotein inhibitior	-	0.9474	94.74%
P-glycoprotein substrate	-	0.9700	97.00%
CYP3A4 substrate	-	0.5378	53.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8134	81.34%
CYP3A4 inhibition	-	0.9171	91.71%
CYP2C9 inhibition	-	0.8562	85.62%
CYP2C19 inhibition	-	0.8671	86.71%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.9288	92.88%
CYP2C8 inhibition	-	0.7987	79.87%
CYP inhibitory promiscuity	-	0.6802	68.02%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6366	63.66%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9516	95.16%
Skin irritation	-	0.8355	83.55%
Skin corrosion	-	0.9678	96.78%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7128	71.28%
Micronuclear	-	0.6082	60.82%
Hepatotoxicity	-	0.8424	84.24%
skin sensitisation	-	0.8164	81.64%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.5560	55.60%
Acute Oral Toxicity (c)	III	0.6179	61.79%
Estrogen receptor binding	-	0.8205	82.05%
Androgen receptor binding	-	0.7402	74.02%
Thyroid receptor binding	-	0.5513	55.13%
Glucocorticoid receptor binding	-	0.7625	76.25%
Aromatase binding	-	0.7294	72.94%
PPAR gamma	+	0.5713	57.13%
Honey bee toxicity	-	0.7581	75.81%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	446.7 nM; 446.7 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.74%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.00%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	83.12%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.87%	96.00%
CHEMBL2581	P07339	Cathepsin D	82.28%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	82.24%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.92%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.67%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.76%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.67%	94.00%

Plants that contains it

• Aegle marmelos
• Ajania fruticulosa
• Alangium chinense
• Alangium platanifolium
• Alangium premnifolium
• Annona glabra
• Astragalus curvicarpus
• Eucalyptus radiata
• Filipendula ulmaria
• Gardenia jasminoides
• Ilex taubertiana
• Imperata cylindrica
• Itoa orientalis
• Laguncularia racemosa
• Populus alba
• Populus balsamifera
• Populus euphratica
• Populus lasiocarpa
• Populus nigra
• Populus tremula
• Populus tremuloides
• Populus trichocarpa
• Salix alba
• Salix babylonica
• Salix caprea
• Salix chaenomeloides
• Salix daphnoides
• Salix gracilistyla
• Salix myrsinifolia
• Salix orestera
• Salix purpurea
• Sonchus oleraceus
• Viburnum rhytidophyllum

Cross-Links

• PubChem: 439503
• NPASS: NPC226712
• ChEMBL: CHEMBL462997
• LOTUS: LTS0129975
• wikiData: Q419173