Structure Database (LMSD)

Common Name
Lepidoxanthin
Systematic Name
(3S,5R,6S,3'R,6'R)-5,6-epoxy-19-(2-decenoyloxy)-19'-acetoxy-4',5'-didehydro-5,6,5',6'-tetrahydro-β,ε-carotene-3,3'-diol
Synonyms
LM ID
LMPR01070945
Formula
C52H74O7
Exact Mass
Calculate m/z
810.543456
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C40 isoprenoids (tetraterpenes) [PR0107]

References

Comments
Imported from http://carotenoiddb.jp/

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Lepidodinium chlorophorum (#107758)
Dinophyceae (#2864)
19,19'-Diacyloxy Signature: An Atypical Level of Structural Evolution in Carotenoid Pigments.,
Org Lett, 2016
Pubmed ID: 27583572

String Representations

InChiKey (Click to copy)
LQEAEODLIWWIFW-QGDBLCQUSA-N
InChi (Click to copy)
InChI=1S/C52H74O7/c1-11-12-13-14-15-16-17-28-48(56)58-38-44(31-32-52-50(8,9)35-46(55)36-51(52,10)59-52)27-21-25-40(3)23-19-18-22-39(2)24-20-26-43(37-57-42(5)53)29-30-47-41(4)33-45(54)34-49(47,6)7/h17-33,45-47,54-55H,11-16,34-38H2,1-10H3/b19-18+,24-20+,25-21+,28-17+,30-29+,32-31+,39-22+,40-23+,43-26-,44-27-/t45-,46-,47-,51+,52-/m0/s1
SMILES (Click to copy)
C1C(C)(C)[C@@]2(O[C@]2(C)C[C@H]1O)/C=C/C(/COC(/C=C/CCCCCCC)=O)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\COC(=O)C)/C=C/[C@H]1C(C)=C[C@H](O)CC1(C)C

Other Databases

PubChem CID
132522595
Carotenoid ID
CA01214

Calculated Physicochemical Properties

Heavy Atoms 59
Rings 3
Aromatic Rings
Rotatable Bonds 23
Van der Waals Molecular Volume 898.29
Topological Polar Surface Area 105.59
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 13.31
Molar Refractivity 245.41

Admin

Created at
17th Nov 2021
Updated at
5th Jan 2022