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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O
Molecular Weight 256.3826
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BAKUCHIOL

SMILES

CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1

InChI

InChIKey=LFYJSSARVMHQJB-QIXNEVBVSA-N
InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1

HIDE SMILES / InChI
Molecular Formula C18H24O
Molecular Weight 256.3826
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28990045 | https://clinicaltrials.gov/ct2/show/NCT03112863 | https://www.ncbi.nlm.nih.gov/pubmed/23831482 | https://www.ncbi.nlm.nih.gov/pubmed/26922230

Bakuchiol is a prenylated phenolic monoterpene isolated from Psoralea corylifolia Leguminosae, widely used in Chinese and Indian traditional medicine for the treatment of premature ejaculation, knee pain, alopecia spermatorrhea, enuresis, backache, pollakiuria, vitiligo, callus, and psoriasis. Bakuchiol is shown to have anti-microbial, anti-inflammatory, anti-oxidative, anti-osteoporosis, and anti-depression or anti-stress activities The anti-cancer potential of bakuchiol has been. Bakuchiol inhibits liver cancer cell growth through inducing S phase arrest, caspase 9/3 activation, p53 and Bax up-regulation, as well as Bcl-2 down-regulation. It also inhibits human carboxylesterase 2, which is commonly expressed in tumor tissue and involved in the metabolism of endogenous lipids and drugs.

Originator

Approval Year

2013
596
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
77.9 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23312380
30 mg/kg single, oral
dose: 30 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAKUCHIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
273.6 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23312380
30 mg/kg single, oral
dose: 30 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAKUCHIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
4269.2 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23312380
15 mg/kg single, intravenous
dose: 15 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BAKUCHIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.9 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23312380
30 mg/kg single, oral
dose: 30 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAKUCHIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
7.23 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23312380
15 mg/kg single, intravenous
dose: 15 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BAKUCHIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037

OverviewOther

Other InhibitorOther SubstrateOther Inducer
UGT2B7
146

UGT2B15
64

UGT2B17
18
CYP1A2
1054

CYP2C19
991

UGT2B4
249

UGT1A3
422

UGT1A8
283

UGT2B7
389

UGT1A4
347

UGT1A6
307

UGT1A9
380

UGT2B15
203

UGT1A7
236

UGT1A10
291

UGT2B17
213

UGT1A1
418
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT2B7
157
 strong [Ki 10.7 uM]
UGT2B15
64
 yes [Inhibition 100 uM]
UGT2B17
20
 yes [Inhibition 100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT1A10
291
 no
UGT1A4
347
 no
UGT1A6
307
 no
UGT1A7
236
 no
UGT1A8
283
 no
UGT1A9
380
 no
UGT2B17
213
 no
UGT2B4
249
 no
UGT2B7
389
 no
UGT1A1
418
 yes
UGT1A3
422
 yes
UGT2B15
203
 yes
CYP1A2
1054
 yes
likely (co-administration study)
Comment: a single oral concomitant dose of BAK and GA increased the internal exposure of rats to BAK and enhanced renal toxicity. The present study demonstrated that GA inhibits CYP isoforms and subsequently might increase the nephrotoxicity of BAK
CYP2C19
991
 yes
likely (co-administration study)
Comment: a single oral concomitant dose of BAK and GA increased the internal exposure of rats to BAK and enhanced renal toxicity. The present study demonstrated that GA inhibits CYP isoforms and subsequently might increase the nephrotoxicity of BAK
CYP2C9
1037
 yes
likely (co-administration study)
Comment: a single oral concomitant dose of BAK and GA increased the internal exposure of rats to BAK and enhanced renal toxicity. The present study demonstrated that GA inhibits CYP isoforms and subsequently might increase the nephrotoxicity of BAK
CYP3A4
1737
 yes
likely (co-administration study)
Comment: a single oral concomitant dose of BAK and GA increased the internal exposure of rats to BAK and enhanced renal toxicity. The present study demonstrated that GA inhibits CYP isoforms and subsequently might increase the nephrotoxicity of BAK
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY115049
https://www.001chemical.com/chem/search?q=DY115049
1PlusChem LLC
1P00349H
https://www.1pchem.com/search?query=1P00349H
AK Scientific
W1975
https://aksci.com/item_detail.php?cat=W1975
Alfa Chemistry
17015-60-0
http://www.alfa-chemistry.com/search.aspx?q=17015-60-0
Ambeed
A182762
http://www.ambeed.com/search/Search.html?keyword=A182762
Angene
AGN-PC-0NVIY7
http://www.angenechemical.com/productshow/AGN-PC-0NVIY7.html
ApexBio Technology
N2310
https://www.apexbt.com/catalogsearch/result/?q=N2310
AstaTech
41774
http://astatechinc.com/CPSResult.php?CRNO=41774
Biopurify Phytochemicals
BP0235
https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0235&searchhtmp=simplesearch&t=1
Cayman Chemical
11684
http://www.caymanchem.com/app/template/Product.vm/catalog/11684
Chem Scene
CS-3749
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3749
Fluorochem
M06038
http://www.fluorochem.co.uk/Products/Product?code=M06038
Hairui
HR100228
http://www.hairuichem.com/en/product/search.do?q=HR100228
KeyOrganics
AS-67675
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-67675
Lab Network
LN00200608
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00200608
Lab Network
LN01275590
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01275590
Matrix Scientific
98340
http://www.matrixscientific.com/098340.html
MedChem Express
HY-N0235
https://www.medchemexpress.com/search.html?q=HY-N0235&ft=&fa=&fp=
MolPort
MolPort-004-960-060
https://www.molport.com/shop/molecule-link/MolPort-004-960-060
MolPort
MolPort-027-835-538
https://www.molport.com/shop/molecule-link/MolPort-027-835-538
Molcore
MC115049
http://www.molcore.com/CatMC115049.html
MuseChem
I000184
https://www.musechem.com/product/I000184.html
PI Chemicals
PI-40716
http://www.pipharm.com/catalog_products/PI-40716.html
Selleck Chemicals
S3813
http://www.selleckchem.com/search.html?searchDTO.searchParam=S3813
TargetMol
10309-37-2
https://www.targetmol.com/search?keyword=10309-37-2
TargetMol
BBP01134
https://www.targetmol.com/search?keyword=BBP01134
TargetMol
T3400
https://www.targetmol.com/search?keyword=T3400
TimTec
ST50309258
http://www.echemstore.com/catalogsearch/result/?q=ST50309258
Toronto Research Chemicals
B115410
https://www.trc-canada.com/product-detail/?CatNum=B115410
Toronto Research Chemicals
D289195
https://www.trc-canada.com/product-detail/?CatNum=D289195
eMolecules
206928153
https://orderbb.emolecules.com/search/#?query=206928153
eMolecules
2726691
https://orderbb.emolecules.com/search/#?query=2726691
eMolecules
300073044
https://orderbb.emolecules.com/search/#?query=300073044
eMolecules
44845564
https://orderbb.emolecules.com/search/#?query=44845564
eMolecules
45915505
https://orderbb.emolecules.com/search/#?query=45915505
eNovation Chemicals
D516823
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D516823&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-2966810763
https://mcule.com/MCULE-2966810763/
mcule
MCULE-4848870516
https://mcule.com/MCULE-4848870516/
mcule
MCULE-5741388716
https://mcule.com/MCULE-5741388716/
PubMed

PubMed

TitleDatePubMed
The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis.
2002 Jan
Bakuchiol-induced caspase-3-dependent apoptosis occurs through c-Jun NH2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts.
2007 Mar 22
Characterization of glutathione conjugates derived from reactive metabolites of bakuchiol.
2016 Jan 25
Patents

Patents

CN107050003
1

Sample Use Guides

In Vivo Use Guide
Rets were treated with bakuchiol at doses of 52.5 and 262.5 mg/kg for 6 weeks.
Route of Administration: Oral
In Vitro Use Guide
The SGC-7901 human gastric cancer cells were seeded on a 96-well plate at 2 × 10^5 cells per well. After 24 h, the cells were treated with bakuchiol at several doses (0, 10, 30, 50, and 100 µM). After incubation times of 12, 24 and 48 h, MTT solution (20 µl) was added. The formazan crystals thus formed were dissolved with DMSO and the absorbance was measured on a microplate reader
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:17:48 GMT 2023
Edited
by admin
on Fri Dec 15 19:17:48 GMT 2023
Record UNII
OT12HJU3AR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAKUCHIOL
INCI  
INCI  
Official Name English
(S)-BAKUCHIOL
Common Name English
(S)-(+)-BAKUCHIOL
Common Name English
(S,E)-4-(3,7-DIMETHYL-3-VINYLOCTA-1,6-DIEN-1-YL)PHENOL
Systematic Name English
SYTENOL A
Brand Name English
PHENOL, 4-(3-ETHENYL-3,7-DIMETHYL-1,6-OCTADIENYL)-, (S-(E))-
Common Name English
(+)-BAKUCHIOL
Common Name English
PHENOL, 4-((1E,3S)-3-ETHENYL-3,7-DIMETHYL-1,6-OCTADIEN-1-YL)-
Systematic Name English
UP-256
Code English
PHENOL, 4-((1E,3S)-3-ETHENYL-3,7-DIMETHYL-1,6-OCTADIENYL)-
Systematic Name English
4-(3-ETHENYL-3,7-DIMETHYL-1,6-OCTADIENYL)PHENOL
Systematic Name English
BAKUCHIOL [INCI]
Common Name English
Code System Code Type Description
FDA UNII
OT12HJU3AR
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
MESH
C012765
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
WIKIPEDIA
Bakuchiol
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID401035664
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
CAS
10309-37-2
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
PUBCHEM
5468522
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
DAILYMED
OT12HJU3AR
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY
RXCUI
1368134
Created by admin on Fri Dec 15 19:17:48 GMT 2023 , Edited by admin on Fri Dec 15 19:17:48 GMT 2023
PRIMARY RxNorm
Related Record Type Details
CULLEN CORYLIFOLIUM FRUIT
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