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Details

Stereochemistry RACEMIC
Molecular Formula C16H25NO
Molecular Weight 247.3758
Optical Activity ( + / - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYCOPODINE, (±)-

SMILES

[H][C@@]12CCCN3CCC[C@]4([H])C(=O)C[C@@H]1C[C@@H](C)C[C@]234

InChI

InChIKey=BCZFSDNVXODRAJ-JTTNIQEDSA-N
InChI=1S/C16H25NO/c1-11-8-12-9-15(18)14-5-3-7-17-6-2-4-13(12)16(14,17)10-11/h11-14H,2-10H2,1H3/t11-,12+,13-,14-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H25NO
Molecular Weight 247.3758
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Miyoshianines A and B, two new lycopodium alkaloids from Huperzia miyoshiana.
2003 Jun
Ten new Lycopodium alkaloids having the lycopodane skeleton isolated from Lycopodium serratum Thunb.
2003 Oct
The Lycopodium alkaloids.
2004 Dec
Anticholinesterase activity in an alkaloid extract of Huperzia saururus.
2004 Sep
[Development of new synthetic method using organometallic complexes and an application toward natural product synthesis].
2005 Jan
Appraisal of anti-inflammatory potential of the clubmoss, Lycopodium clavatum L.
2007 Jan 3
Enantioselective total synthesis of lycopodine.
2008 Jul 23
In vitro biological activity screening of Lycopodium complanatum L. ssp. chamaecyparissus (A. Br.) Doll.
2009
Detection by UPLC/ESI-TOF-MS of alkaloids in three Lycopodiaceae species from French Polynesia and their anticholinesterase activity.
2009 Oct
Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.
2010 Aug 6
Lycopodine from Lycopodium clavatum extract inhibits proliferation of HeLa cells through induction of apoptosis via caspase-3 activation.
2010 Jan 25
Comparison of 454-ESTs from Huperzia serrata and Phlegmariurus carinatus reveals putative genes involved in lycopodium alkaloid biosynthesis and developmental regulation.
2010 Sep 21
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:18:12 GMT 2023
Edited
by admin
on Sat Dec 16 08:18:12 GMT 2023
Record UNII
NTV9A2GW9H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LYCOPODINE, (±)-
Common Name English
LYCOPODAN-5-ONE, 15-METHYL-, (15R)-(±)-
Common Name English
1,9-ETHANOBENZO(I)QUINOLIZIN-14-ONE, DODECAHYDRO-11-METHYL-, (1R,8AS,9R,11S,12AS)-REL-
Systematic Name English
DL-LYCOPODINE
Common Name English
(15R)-15-METHYLLYCOPODAN-5-ONE, (±)-
Common Name English
(±)-LYCOPODINE
Common Name English
Code System Code Type Description
CAS
18688-24-9
Created by admin on Sat Dec 16 08:18:12 GMT 2023 , Edited by admin on Sat Dec 16 08:18:12 GMT 2023
PRIMARY
PUBCHEM
5462445
Created by admin on Sat Dec 16 08:18:12 GMT 2023 , Edited by admin on Sat Dec 16 08:18:12 GMT 2023
PRIMARY
FDA UNII
NTV9A2GW9H
Created by admin on Sat Dec 16 08:18:12 GMT 2023 , Edited by admin on Sat Dec 16 08:18:12 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE