Structure Database (LMSD)

HO OH HO
Common Name
5-Hydroxyeschscholtzxanthin
Systematic Name
(3S,5R,3'S)-4',5'-Didehydro-5,6-dihydro-6,5'-retro-β,β-carotene-3,5,3'-triol
Synonyms
LM ID
LMPR01070657
Formula
C40H56O3
Exact Mass
Calculate m/z
584.422945
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)
GVOORTVDJMSUHI-AWOSIHMVSA-N
InChi (Click to copy)
InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37-39(8,9)27-35(42)28-40(37,10)43/h11-25,34-35,41-43H,26-28H2,1-10H3/b15-11+,16-12+,19-13+,20-14+,29-17+,30-18+,31-21+,32-22+,36-23-,37-24+/t34-,35-,40+/m1/s1
SMILES (Click to copy)
C1[C@](C)(O)/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[C@H](O)C=C\2C)/C(C)(C)C[C@H]1O

References

Comments
Imported from http://carotenoiddb.jp/

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Eschscholzia californica (#3467)
Magnoliopsida (#3398)
A new retro-carotenoid from the petals of the Californian yellow poppy Eschscholtzia californica.,
J Nat Prod, 2000
Pubmed ID: 11000040

Other Databases

PubChem CID
162995775
Carotenoid ID
CA00342

Calculated Physicochemical Properties

Heavy Atoms 43
Rings 2
Aromatic Rings
Rotatable Bonds 9
Van der Waals Molecular Volume 673.17
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 10.38
Molar Refractivity 187.10

Admin

Created at
17th Nov 2021
Updated at
2nd Dec 2021