BAKUCHIOL

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27685910
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

Targets

Primary Target	Pharmacology	Condition	Potency
PI3K/AKT Signaling in Cancer 2 Target ID: WP3544 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28990045	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Wrinkles 2 Sources: https://clinicaltrials.gov/ct2/show/NCT03112863	Primary		Phase II 1132	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27685910	Primary		Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other 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

Target	Modality	Activity
UGT2B7 157	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4209642/	strong [Ki 10.7 uM]
UGT2B15 64	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4209642/	yes [Inhibition 100 uM]
UGT2B17 20	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4209642/	yes [Inhibition 100 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT2B17 213	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	no
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	yes
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	yes
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27314830/ Page: 6.0	yes
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/	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 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/	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 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/	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 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/	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 Sources: https://pubmed.ncbi.nlm.nih.gov/22692316/;https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5126668/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis.	2002 Jan	11744296
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	17292878
Characterization of glutathione conjugates derived from reactive metabolites of bakuchiol.	2016 Jan 25	26712081

Patents

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

Name

Type

Language

BAKUCHIOL

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