Icariin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Icariin
DrugBank Accession Number
DB12052
Background

Icariin has been investigated for the basic science of the Pharmacokinetic Profile of Icariin in Humans.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 676.668
Monoisotopic: 676.236720588
Chemical Formula
C33H40O15
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavonoid glycosides
Direct Parent
Flavonoid-7-O-glycosides
Alternative Parents
8-prenylated flavones / Flavonoid-3-O-glycosides / 4'-O-methylated flavonoids / 5-hydroxyflavonoids / Phenolic glycosides / Chromones / O-glycosyl compounds / Anisoles / Methoxybenzenes / Phenoxy compounds
show 14 more
Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 4p-methoxyflavonoid-skeleton / 5-hydroxyflavonoid / 8-prenylated flavone / Acetal / Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
glycosyloxyflavone, flavonols (CHEBI:78420) / Flavones and Flavonols (C17555)
Affected organisms
Not Available

Chemical Identifiers

UNII
VNM47R2QSQ
CAS number
489-32-7
InChI Key
TZJALUIVHRYQQB-XLRXWWTNSA-N
InChI
InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1
IUPAC Name
5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
SMILES
COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(CC=C(C)C)=C2O1

References

General References
Not Available
KEGG Compound
C17555
PubChem Compound
5318997
PubChem Substance
347828363
ChemSpider
4477421
BindingDB
50027363
RxNav
1788871
ChEBI
78420
ChEMBL
CHEMBL553204
ZINC
ZINC000003960893
Wikipedia
Icariin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentBipolar Disorder (BD) / Substance Use Disorders (SUD)1
1CompletedBasic ScienceThe Pharmacokinetic Profile of Icariin in Humans1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.612 mg/mLALOGPS
logP0.71ALOGPS
logP0.81Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)7.07Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count15Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area234.29 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity166.62 m3·mol-1Chemaxon
Polarizability68.44 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-014i-0009010000-167db01481198b102b0e
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-00di-0000000900-3b6c981c418eb6e5ac7b
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-00di-0000020900-131c1c68f1f1b1537632
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-03di-0000090000-9de31877ecd025afa487
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-03xr-0003090000-2f314f54d3758131b887
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-014i-0009030000-86bc75df7adfcdc54933
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0000290000-28beb3b038d0e2d6bea4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0300129000-55c1bbfd80704a03a691
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0109581000-a99b2bd173fff1616722
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ud-1600269000-a6781ca4fc091cbe00ed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-2205195000-8496b472784caa056c94
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00or-1108169000-c110a89cf8ee3a10d088
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-270.205316
predicted
DarkChem Lite v0.1.0
[M-H]-242.09882
predicted
DeepCCS 1.0 (2019)
[M+H]+267.066316
predicted
DarkChem Lite v0.1.0
[M+H]+243.82254
predicted
DeepCCS 1.0 (2019)
[M+Na]+266.535316
predicted
DarkChem Lite v0.1.0
[M+Na]+250.17377
predicted
DeepCCS 1.0 (2019)

Drug created at October 20, 2016 21:16 / Updated at June 12, 2020 16:53