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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12O5
Molecular Weight 260.2426
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KHELLIN

SMILES

Cc1cc(=O)c2c(c3ccoc3c(c2o1)OC)OC

InChI

InChIKey=HSMPDPBYAYSOBC-UHFFFAOYSA-N
InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

HIDE SMILES / InChI

Molecular Formula C14H12O5
Molecular Weight 260.2426
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Khellin is a crystalline extract of a crude drug, which has long been used in Egypt for the treatment of ureteral colic. It is used in the management of bronchial asthma and angina pectoris. Interest in khellin as an adjunct to ultraviolet (UV) light therapy in the treatment of vitiligo is based on the structural similarity between khellin and the psoralens. Success has been reported using oral and topical khellin in clinical studies but it is not likely that khellin will be approved for the treatment of vitiligo. Unwanted side effects of khellin include dizziness, reversible cholestatic jaundice, pseudoallergic reaction, and elevated levels of liver enzymes (transaminases and gamma-glutamyltransferase).

Originator

Sources: DOI: 10.1002/cber.19380710118

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Calcium influx
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ammivin

Approved Use

Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Palliative
Ammivin

Approved Use

Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Palliative
Ammivin

Approved Use

Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
weak [IC50 34.6 uM]
yes [IC50 0.04 uM]
yes [IC50 4.02 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Expression analyses of sex steroid-regulated genes in neonatal rat hypothalamus.
2003 Dec
The chemical investigations on the ripe fruits of Ammi visnaga (Lam.) Lamarck growing in Turkey.
2004 Apr
Genetic characterization of the Drosophila homologue of coronin.
2004 Apr 15
Coronin 7, the mammalian POD-1 homologue, localizes to the Golgi apparatus.
2004 Aug 27
The two neutrophil members of the formylpeptide receptor family activate the NADPH-oxidase through signals that differ in sensitivity to a gelsolin derived phosphoinositide-binding peptide.
2004 Dec 29
Cytotoxic activity of five compounds isolated from Colombian plants.
2004 Mar
Cholesterol-sensor initiates M. tuberculosis entry into human macrophages.
2004 Mar
Treatment of vitiligo with local khellin and UVA: comparison with systemic PUVA.
2004 Mar
Topical khellin and natural sunlight in the outpatient treatment of recalcitrant palmoplantar pompholyx: report of an open pilot study.
2005
Homotypic dimerization of the actin-binding protein p57/coronin-1 mediated by a leucine zipper motif in the C-terminal region.
2005 Apr 15
Conformational changes in the Arp2/3 complex leading to actin nucleation.
2005 Jan
In vivo and in vitro characterization of novel neuronal plasticity factors identified following spinal cord injury.
2005 Jan 21
Gene expression in the brain and kidney of rainbow trout in response to handling stress.
2005 Jan 6
Dynamic properties of Legionella-containing phagosomes in Dictyostelium amoebae.
2005 Jul
Proteomic identification of less oxidized brain proteins in aged senescence-accelerated mice following administration of antisense oligonucleotide directed at the Abeta region of amyloid precursor protein.
2005 Jul 29
Coronin proteins as multifunctional regulators of the cytoskeleton and membrane trafficking.
2005 Jun
Acanthamoeba healyi: molecular cloning and characterization of a coronin homologue, an actin-related protein.
2005 Jun
Coronin 3 and its role in murine brain morphogenesis.
2005 Mar
Measurement of daphnoretin in plasma of freely moving rat by liquid chromatography.
2005 May 6
A novel homologue of coronin colocalizes with actin in filament-like structures in Leishmania.
2005 Oct
A single-nucleotide polymorphism in the gene encoding lymphoid protein tyrosine phosphatase (PTPN22) confers susceptibility to generalised vitiligo.
2005 Oct
Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions.
2005 Oct 20
Downregulation of TACO gene transcription restricts mycobacterial entry/survival within human macrophages.
2005 Sep 1
Phosphorylation of coronin 1B by protein kinase C regulates interaction with Arp2/3 and cell motility.
2005 Sep 9
Green tea polyphenol inhibits Mycobacterium tuberculosis survival within human macrophages.
2006
Application of 1D BIRD or X-filtered DEPT long-range C-C relay for detection of proton and carbon via four bonds and measuring long-range 13C-13C coupling constants.
2006 Apr
Coronins: the return of the crown.
2006 Aug
Effusion and solid lymphomas have distinctive gene and protein expression profiles in an animal model of primary effusion lymphoma.
2006 Aug
Requirement for coronin 1 in T lymphocyte trafficking and cellular homeostasis.
2006 Aug 11
Immunology. When F-actin becomes too much of a good thing.
2006 Aug 11
Transcriptional regulation of artemin is related to neurite outgrowth and actin polymerization in mature DRG neurons.
2006 Aug 14
Time-resolved responses to chemoattractant, characteristic of the front and tail of Dictyostelium cells.
2006 Dec 11
The identification of a new actin-binding region in p57.
2006 Jan
The crystal structure of murine coronin-1: a regulator of actin cytoskeletal dynamics in lymphocytes.
2006 Jan
Ultraviolet photoionization of the photosensitizers khellin and visnagin in aqueous solution and in micelles: one-photon ionization is a minor process.
2006 Mar
Microtubules regulate disassembly of epithelial apical junctions.
2006 Mar 1
The tumor suppressor protein p53 is required for neurite outgrowth and axon regeneration.
2006 Sep 6
Lipoamide dehydrogenase mediates retention of coronin-1 on BCG vacuoles, leading to arrest in phagosome maturation.
2007 Aug 15
Neuronal morphogenesis is regulated by the interplay between cyclin-dependent kinase 5 and the ubiquitin ligase mind bomb 1.
2007 Aug 29
Actin-binding proteins coronin-1a and IBA-1 are effective microglial markers for immunohistochemistry.
2007 Jul
Survival of mycobacteria in macrophages is mediated by coronin 1-dependent activation of calcineurin.
2007 Jul 13
Coronin 3 involvement in F-actin-dependent processes at the cell cortex.
2007 Mar 10
F-actin binding is essential for coronin 1B function in vivo.
2007 May 15
An actin-based wave generator organizes cell motility.
2007 Sep
Competition between targeting signals in hybrid proteins provides information on their relative in vivo affinities for subcellular compartments.
2008 Feb
Coronin-1A stabilizes F-actin by bridging adjacent actin protomers and stapling opposite strands of the actin filament.
2008 Feb 22
The lupus-related Lmb3 locus contains a disease-suppressing Coronin-1A gene mutation.
2008 Jan
Distinct roles for Arp2/3 regulators in actin assembly and endocytosis.
2008 Jan
Expression of coronin-3 (coronin-1C) in diffuse gliomas is related to malignancy.
2008 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Oral: 200 mg/day Topical: as a 2% preparation
Route of Administration: Other
In Vitro Use Guide
In neutral O2-saturated aqueous solution, the photosensitized His degradation quantum yield is about 8x10(-5) for khellin. In O2-saturated aqueous solution, khellin photosensitized the oxidation of Trp with a quantum yield of 1.5x10(-4), which is quite low.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:39:11 UTC 2021
Edited
by admin
on Sat Jun 26 11:39:11 UTC 2021
Record UNII
5G117T0TJZ
Record Status Validated (UNII)
Record Version
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Name Type Language
KHELLIN
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NSC-37744
Code English
KHELLIN [INN]
Common Name English
KHELLIN [MI]
Common Name English
4,9-DIMETHOXY-7-METHYL-5H-FURO(3,2-G)(1)BENZOPYRAN-5-ONE
Systematic Name English
VISCARDAN
Brand Name English
KHELLIN [MART.]
Common Name English
KHELLIN [WHO-DD]
Common Name English
NSC-25509
Code English
4,9-DIMETHOXY-7-METHYL-5-OXOFURO(3,2-G)-1,2-CHROMENE
Common Name English
AMMIVIN
Brand Name English
KHELLOYD
Brand Name English
CORONIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C45597
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
Code System Code Type Description
MERCK INDEX
M6626
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY Merck Index
EVMPD
SUB08380MIG
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
NCI_THESAURUS
C75957
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
FDA UNII
5G117T0TJZ
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-392-8
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
CAS
82-02-0
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
RXCUI
6147
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY RxNorm
INN
192
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
MESH
D007666
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
PUBCHEM
3828
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
EPA CompTox
82-02-0
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL44746
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
WIKIPEDIA
KHELLIN
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
DRUG CENTRAL
3313
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
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