Structure Database (LMSD)

O OH
Common Name
Eschscholtzxanthone
Systematic Name
(3'S)-3'-Hydroxy-4',5'-didehydro-4,5'-retro-β,β-caroten-3-one
Synonyms
LM ID
LMPR01070044
Formula
C40H52O2
Exact Mass
Calculate m/z
564.39673
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

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

String Representations

InChiKey (Click to copy)
GDALYDGIVMUXTI-AKBIDAKBSA-N
InChi (Click to copy)
InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-26,35,41H,27-28H2,1-10H3/b15-11+,16-12+,19-13+,20-14+,29-17+,30-18+,31-21+,32-22+,37-23+,38-24+/t35-/m1/s1
SMILES (Click to copy)
C1C(C)(C)/C(=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C/C(/C)=C/C=C/C(/C)=C/C=C2\C(C)=C[C@@H](O)CC\2(C)C)/C(C)=CC1=O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Taxus cuspidata (#99806)
Pinopsida (#58019)
Structures and Antioxidative Activity of retro Carotenoids from the Berries of the Japanese Yew, Taxus cuspidata,
J. Jap. Oil Chem. Soc, 1996

Other Databases

LIPIDBANK ID
VCA0042
PubChem CID
16061205

Calculated Physicochemical Properties

Heavy Atoms 42
Rings 2
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 659.10
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 10.82
Molar Refractivity 183.59

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Created at
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Updated at
22nd Mar 2024