U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18O4
Molecular Weight 262.301
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HELENALIN

SMILES

[H][C@@]12C[C@@H](C)[C@]3([H])C=CC(=O)[C@@]3(C)[C@@H](O)[C@]1([H])C(=C)C(=O)O2

InChI

InChIKey=ZVLOPMNVFLSSAA-XEPQRQSNSA-N
InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H18O4
Molecular Weight 262.301
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of homodimerization of Toll-like receptor 4 by curcumin.
2006 Jun 28
Inhibition of Nod2 signaling and target gene expression by curcumin.
2008 Jul
Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress.
2009 Aug
Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma.
2013 Mar
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:44:05 GMT 2023
Edited
by admin
on Fri Dec 15 19:44:05 GMT 2023
Record UNII
4GUY9L896T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HELENALIN
HSDB   MI  
Common Name English
6.ALPHA.,8.BETA.-DIHYDROXY-4-OXOAMBROSA-2,11(13)-DIEN-12-OIC ACID 12,8-LACTONE
Common Name English
(-)-HELENALIN
Common Name English
HELENALIN [MI]
Common Name English
HELENALIN [HSDB]
Common Name English
(3AS-(3A.ALPHA.,4.ALPHA.,4A.BETA.,7A.ALPHA.,8.ALPHA.,9A.ALPHA.))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE
Common Name English
NSC-85236
Code English
Code System Code Type Description
HSDB
3490
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
PUBCHEM
23205
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
WIKIPEDIA
HELENALIN
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
MESH
C001329
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
NSC
85236
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID50217868
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
FDA UNII
4GUY9L896T
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
CAS
6754-13-8
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY
MERCK INDEX
m5931
Created by admin on Fri Dec 15 19:44:05 GMT 2023 , Edited by admin on Fri Dec 15 19:44:05 GMT 2023
PRIMARY Merck Index
Related Record Type Details
TARGET -> INHIBITOR
Helenalin selectively alkylates p65 subunit at Cys38 [27, 63]. Formation of this covalent bond sterically prevents the p50/p65 heterodimer from binding to DNA and therefore inhibits its transcriptional activation.
TARGET -> INHIBITOR
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
TARGET -> INHIBITOR
Helenalin binds to Cys445 of telomerase in the Michael-type addition reaction, disturbing recognition of the telomere DNA at the telomerase active site and causing suppression of the enzyme activity.
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT