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Details

Stereochemistry ACHIRAL
Molecular Formula C45H74O
Molecular Weight 631.0685
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 8
Charge 0

SHOW SMILES / InChI
Structure of SOLANESOL

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

InChI

InChIKey=AFPLNGZPBSKHHQ-MEGGAXOGSA-N
InChI=1S/C45H74O/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)33-18-34-45(10)35-36-46/h19,21,23,25,27,29,31,33,35,46H,11-18,20,22,24,26,28,30,32,34,36H2,1-10H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-33+,45-35+

HIDE SMILES / InChI
Solanesol is a naturally occurring isoprenoid and the most abundant lipid in tobacco leaves. It is also found in tomato, potato, eggplant, and pepper plants. Solanesol is widely used in the pharmaceutical industry as an intermediate for the synthesis of ubiquinone drugs, such as coenzyme Q10 and vitamin K2. Solanesol possesses antibacterial, antifungal, antiviral, anticancer, anti-inflammatory, and anti-ulcer activities, and solanesol derivatives also have anti-oxidant and antitumor activities. Solanesol has been shown to increase the expression of HO-1 and Hsp70 which may contribute to the prevention of ethanol-induced cell damage. Solanesol is readily introduced into the body as a component of tobacco smoke.

Originator

Curator's Comment: Stevenson J, Hemming FW, Morton RA.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P09601
Gene ID: 3162.0
Gene Symbol: HMOX1
Target Organism: Homo sapiens (Human)
Target ID: P0DMV8
Gene ID: 3303|||3304
Gene Symbol: HSPA1A
Target Organism: Homo sapiens (Human)
Target ID: P14679
Gene ID: 7299.0
Gene Symbol: TYR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Antioxidant function of solanesol and its inhibitory effect on tyrosinase].
2014 Aug
Solanesol protects human hepatic L02 cells from ethanol-induced oxidative injury via upregulation of HO-1 and Hsp70.
2015 Apr
Patents

Sample Use Guides

Ten cigaret smokers took seven puffs from a 10 mg 'tar' yield test cigaret and a fixed volume of air (0, 75, 250, 500 or 1000 mL) to give controlled depth of inhalation. Subjects exhaled normally after a 2-second breath hold with exhalation passing through a filter pad for the collection of non-retained nicotine and solanesol. Blood samples were taken before and at intervals during and after smoking. A second series of experiments was conducted with a fixed inhalation volume (500 mL) and three breath hold durations (0, 2, and 10 seconds). Solanesol retention increased from 34.2% at zero inhalation volume to 71.9% at 1000 mL inhalation volume ( for 2-second breath hold) and from 51.8% at zero breath hold to 87.6% at 10-second breath hold (500 mL inhalation).
Route of Administration: Respiratory
Normal human hepatic cell L02 was cultured in DMEM media containig 10% (v/v) fetal bovine serum, 100 U/mL penicillin and 100 micro-g/mL streptomycin at 37 deg-C ina 5% CO2 atmosphere. Cells were cultured with different concentrations of solanesol (0 - 80 micro-M) for 12 hours. Relative HO-1 and Hsp70 mRNA expressions were determined using real-time polymer chain reaction and calculated by subtracting the Ct value for GAPDH from the Ct value for HO-1 or Hsp70. Solanesol increased mRNA and protein levels of HO-1 and Hsp70 in a dose-dependent manner.
Name Type Language
SOLANESOL
MI  
Common Name English
2,6,10,14,18,22,26,30,34-HEXATRIACONTANONAEN-1-OL, 3,7,11,15,19,23,27,31,35-NONAMETHYL-, (2E,6E,10E,14E,18E,22E,26E,30E)-
Systematic Name English
FARNESYLFARNESYLFARNESOL
Systematic Name English
SOLANESOL [MI]
Common Name English
NONAISOPRENOL
Common Name English
2,6,10,14,18,22,26,30,34-HEXATRIACONTANONAEN-1-OL, 3,7,11,15,19,23,27,31,35-NONAMETHYL-, (ALL-E)-
Common Name English
Code System Code Type Description
FDA UNII
FF31XTR2N4
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID60884580
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
PRIMARY
MESH
C017719
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
PRIMARY
CAS
13190-97-1
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
PRIMARY
WIKIPEDIA
Solanesol
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
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MERCK INDEX
m10100
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
PRIMARY Merck Index
PUBCHEM
5477212
Created by admin on Sat Dec 16 04:14:50 UTC 2023 , Edited by admin on Sat Dec 16 04:14:50 UTC 2023
PRIMARY