U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H18O7
Molecular Weight 286.2778
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALICIN

SMILES

OC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=NGFMICBWJRZIBI-UJPOAAIJSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25907238

The most well known component of willow bark extract is salicin, it is a prodrug, which is gradually transported to the lower part of the intestine, hydrolyzed to saligenin by intestinal bacteria, and converted to salicylic acid after absorption. Salicin possesses an analgesic, anti-inflammatory, and antipyretic properties. Salicin suppressed the activation of MAPKs and NF-κB signaling pathways and thus maybe might be a potential therapeutic agent against inflammatory diseases.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10.7 μM × h
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
N-SALICYLOYLGLYCINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
99 μM × h
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SALICYLIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.9 μM × h
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GENTISIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.45 h
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SALICYLIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Isolation of salicin derivatives from Homalium cochinchinensis and their antiviral activities.
2004 Apr
Purification and characterization of an extracellular b-glucosidase with high transglucosylation activity and stability from Aspergillus niger No. 5.1.
2004 Dec
Differentiation of extractive and synthetic salicin. The 2H aromatic pattern of natural 2-hydroxybenzyl alcohol.
2004 Dec 29
[Purification of lectin from perch (Persa fluviatilis L.) roe specific to cellobiose and study of its characteristics].
2004 Jan-Feb
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov.
2004 May
Analysis of bgl operon structure and characterization of beta-glucosidase from Pectobacterium carotovorum subsp. carotovorum LY34.
2004 Nov
Bitter taste receptors for saccharin and acesulfame K.
2004 Nov 10
[Life threatening intestinal bleeding in a Bearded Collie associated with a food supplement for horses].
2004 Oct
Isolation and characterization of a cellulolytic Geobacillus thermoleovorans T4 strain from sugar refinery wastewater.
2004 Oct
The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae.
2004 Oct
Mechanisms involved in the anti-inflammatory effect of a standardized willow bark extract.
2005
Sample pretreatment and determination of non steroidal anti-inflammatory drugs (NSAIDs) in pharmaceutical formulations and biological samples (blood, plasma, erythrocytes) by HPLC-UV-MS and micro-HPLC.
2005
Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction.
2005 Apr 20
A digestive beta-glucosidase from the silkworm, Bombyx mori: cDNA cloning, expression and enzymatic characterization.
2005 Aug
Analysis of carbohydrates in plants by high-performance anion-exchange chromatography coupled with electrospray mass spectrometry.
2005 Aug 26
Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris.
2005 Dec
Electrophysiological and behavioural characterization of gustatory responses to antennal 'bitter' taste in honeybees.
2005 Dec
Purification and characterization of recombinant Escherichia coli-expressed Pichia etchellsii beta-glucosidase II with high hydrolytic activity on sophorose.
2005 Feb
Emetic toxin formation of Bacillus cereus is restricted to a single evolutionary lineage of closely related strains.
2005 Jan
Positive selection on a high-sensitivity allele of the human bitter-taste receptor TAS2R16.
2005 Jul 26
Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae).
2005 Jul 27
Aerococcus urinae: polyphasic characterization of the species.
2005 Jul-Aug
Genetic variability among Blastoschizomyces capitatus isolates from different clinical sources.
2005 Jul-Sep
[Arbutin, salicin: the possibilities of their biotechnological production].
2005 Mar
Structural and biochemical analysis of the asc operon encoding 6-phospho-beta-glucosidase in Pectobacterium carotovorum subsp. carotovorum LY34.
2005 Mar
Emergence of unusual species of enterococci causing infections, South India.
2005 Mar 17
Comparison of molecular mobility in the glassy state between amorphous indomethacin and salicin based on spin-lattice relaxation times.
2005 May
Semi-industrial isolation of salicin and amygdalin from plant extracts using slow rotary counter-current chromatography.
2005 May 13
Stable isotope characterization of the ortho-oxygenated phenylpropanoids: coumarin and melilotol.
2005 Nov 30
HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations.
2005 Nov-Dec
Pyrosequencing Bacillus anthracis.
2005 Oct
Purification and characterization of two endo-beta-1,4-glucanases from mollusca, Ampullaria crossean.
2005 Oct
Lactobacillus concavus sp. nov., isolated from the walls of a distilled spirit fermenting cellar in China.
2005 Sep
Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence.
2006
Cloning and comparison of third beta-glucoside utilization (bglEFIA) operon with two operons of Pectobacterium carotovorum subsp. carotovorum LY34.
2006 Apr
The historical analysis of aspirin discovery, its relation to the willow tree and antiproliferative and anticancer potential.
2006 Apr
Herbal medicine for low back pain.
2006 Apr 19
Conflicting demands on detoxification pathways influence how common brushtail possums choose their diets.
2006 Aug
Allergy-preventive phenolic glycosides from Populus sieboldii.
2006 Aug
Arabidopsis thaliana beta-Glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides.
2006 Aug
Temporal coding mediates discrimination of "bitter" taste stimuli by an insect.
2006 Aug 30
Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada.
2006 Aug 7
Genomic variation in Streptococcus mutans: deletions affecting the multiple pathways of beta-glucoside metabolism.
2006 Feb
Metabolic pathways variability and sequence/networks comparisons.
2006 Jan 18
[The Italian contributions to the history of salicylates].
2006 Jan-Mar
Monitoring carbohydrate enzymatic reactions by quantitative in vitro microdialysis.
2006 Jun 16
The expression of genes encoding lipodepsipeptide phytotoxins by Pseudomonas syringae pv. syringae is coordinated in response to plant signal molecules.
2006 Mar
Inhibition activities of natural products on serine proteases.
2006 Mar
Reclassification of Paenibacillus larvae subsp. pulvifaciens and Paenibacillus larvae subsp. larvae as Paenibacillus larvae without subspecies differentiation.
2006 Mar
Sugarcane ShSUT1: analysis of sucrose transport activity and inhibition by sucralose.
2006 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/24240229
for rats (fever): Orally administered SL (SALICIN) did not affect the rectal temperatures at a dose of 5 mmol/kg for mice (colitis): 100 and 200 mg per body weight was administered daily through oral gavage for 7 days
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: It was evaluated the effect of D(-)-Salicin on cytokines (TNF-α, IL-1β, IL-6 and IL-10) in vivo and in vitro by enzyme-linked immunosorbent assay.The results showed that D(-)-Salicin markedly decreased TNF-α, IL-1β and IL-6 concentrations and increased IL-10 concentration.
Unknown
Name Type Language
SALICIN
INCI   MI   WHO-DD  
INCI  
Official Name English
SALICYL ALCOHOL GLUCOSIDE
Common Name English
D(-)-SALICIN
Common Name English
SALICIN [INCI]
Common Name English
SALICOSIDE
Common Name English
NSC-5751
Code English
D-(-)-SALICIN
Common Name English
2-(HYDROXYMETHYL)PHENYL-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
SALICINUM
HPUS  
Common Name English
SALICINUM [HPUS]
Common Name English
D-SALICIN [USP-RS]
Common Name English
Salicyl alcohol glucoside [WHO-DD]
Common Name English
SALICIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
DSLD 2450 (Number of products:17)
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL462997
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
DAILYMED
4649620TBZ
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
RXCUI
36100
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PRIMARY RxNorm
ECHA (EC/EINECS)
205-331-6
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PRIMARY
CHEBI
17814
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
NSC
5751
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PRIMARY
SMS_ID
100000078369
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PRIMARY
PUBCHEM
439503
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PRIMARY
EPA CompTox
DTXSID10883326
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PRIMARY
RS_ITEM_NUM
1607903
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
WIKIPEDIA
SALICIN
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
MERCK INDEX
m9730
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY Merck Index
FDA UNII
4649620TBZ
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PRIMARY
CAS
138-52-3
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PRIMARY
NCI_THESAURUS
C90648
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
MESH
C005696
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY
EVMPD
SUB15176MIG
Created by admin on Fri Dec 15 16:38:24 GMT 2023 , Edited by admin on Fri Dec 15 16:38:24 GMT 2023
PRIMARY