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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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
77.9 ng/mL
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
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
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
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
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


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
strong [Ki 10.7 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
yes
yes
yes
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
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
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
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
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

Sample Use Guides

Rets were treated with bakuchiol at doses of 52.5 and 262.5 mg/kg for 6 weeks.
Route of Administration: Oral
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
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