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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12O5
Molecular Weight 272.2528
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BUTEIN

SMILES

OC1=CC=C(C(=O)\C=C\C2=CC=C(O)C(O)=C2)C(O)=C1

InChI

InChIKey=AYMYWHCQALZEGT-ORCRQEGFSA-N
InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

HIDE SMILES / InChI

Molecular Formula C15H12O5
Molecular Weight 272.2528
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Butein, a plant polyphenol, has been reported to exhibit several important pharmacological effects, such as anti-inflammatory, anti-cancer, anti-oxidant and anti-angiogenic. It was first found in Toxicodendronvernicifluum, a tree widely used as a local food additive and therapeutic supplement in South East Asia. It can also be isolated from the heartwood of Dalbergiaodorifera, the seed of Cyclopiasubternata and the stems of Semecarpusanacardium, as well as many other plants. Butein was shown to be a specific protein tyrosine kinase inhibitor. This compound inhibited tyrosine-specific protein kinase activities of EGF receptor and p60(c-Src). In preclinical settings, it was shown to improve the treatment outcome of several chronic diseases including inflammation, neurological disorders, neoplasms, atherosclerosis, as well as infectious diseases, and most of these actions were accomplished by the inhibition of the transcription factor NF-κB and its downstream targets.

Originator

Sources: DOI: 10.1039/CT9048501459

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
65.0 µM [IC50]
16.0 µM [IC50]
Target ID: Glutathione S-transferase (rat)
9.0 µM [IC50]
3.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.
1998 Oct 8
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
2000 Sep
The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation.
2007 Mar
Butein protects human dental pulp cells from hydrogen peroxide-induced oxidative toxicity via Nrf2 pathway-dependent heme oxygenase-1 expressions.
2013 Mar
The depletion of securin enhances butein-induced apoptosis and tumor inhibition in human colorectal cancer.
2014 Sep 5
Patents

Sample Use Guides

Mice: 1, 3 or 10 mg/kg was administered every day from 3 days before tumor cell injection to 21 days after tumor cell injection.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Butein up to 500 uM scarcely inhibited protein kinase C and cAMP-dependent protein kinase activities in HepG2 cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:48:35 GMT 2023
Edited
by admin
on Fri Dec 15 17:48:35 GMT 2023
Record UNII
4WVS5M0LGF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTEIN
Common Name English
2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(3,4-DIHYDROXYPHENYL)-
Systematic Name English
2',3,4,4'-TETRAHYDROXYCHALCONE
Systematic Name English
3,4,2',4'-TETRAHYDROXYCHALCONE
Systematic Name English
2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(3,4-DIHYDROXYPHENYL)-, (2E)-
Systematic Name English
NSC-652892
Code English
TETRAHYDROXYCHALCONE, 3,4,2',4'-
Systematic Name English
2',4',3,4-TETRAHYDROXYCHALCONE
Systematic Name English
CHALCONE, 2',3,4,4'-TETRAHYDROXY-
Systematic Name English
2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(3,4-DIHYDROXYPHENYL)-, (E)-
Systematic Name English
ISOLIQUIRITIGENIN METABOLITE M4
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
Code System Code Type Description
FDA UNII
4WVS5M0LGF
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
PUBCHEM
5281222
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID101025569
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
CAS
21849-70-7
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
CAS
487-52-5
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
NCI_THESAURUS
C1028
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
WIKIPEDIA
BUTEIN
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
CHEBI
3237
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-659-5
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
NSC
652892
Created by admin on Fri Dec 15 17:48:35 GMT 2023 , Edited by admin on Fri Dec 15 17:48:35 GMT 2023
PRIMARY
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