Structure Database (LMSD)

Common Name
Cycloartenyl ferulate
Systematic Name
9β,19-cyclolanost-24-en-3β-yl ferulate
Synonyms
  • gamma-Oryzanol
  • 3-O-Ferulylcycloartenol
LM ID
LMST05050066
Formula
C40H58O4
Exact Mass
Calculate m/z
602.43351
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Other Steroid conjugates [ST0505]
Sterols [ST01]
Cycloartanols and derivatives [ST0110]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Oryza sativa (#4530)
Magnoliopsida (#3398)
Purification and identification of components of gamma-oryzanol in rice bran Oil.,
J Agric Food Chem, 1999
Pubmed ID: 10552553

String Representations

InChiKey (Click to copy)
FODTZLFLDFKIQH-FSVGXZBPSA-N
InChi (Click to copy)
InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+/t27-,29-,32+,33+,34+,37-,38+,39-,40+/m1/s1
SMILES (Click to copy)
C1=C(OC)C(O)=CC=C1/C=C/C(O[C@@H]1C(C)(C)[C@@]2([H])[C@]3(C[C@@]43CC[C@]3(C)[C@]([C@H](C)CC/C=C(\C)/C)([H])CC[C@@]3(C)[C@]4([H])CC2)CC1)=O

Other Databases

KEGG ID
D01221
CHEBI ID
32345
PubChem CID
5282164

Calculated Physicochemical Properties

Heavy Atoms 44
Rings 6
Aromatic Rings 1
Rotatable Bonds 9
Van der Waals Molecular Volume 634.82
Topological Polar Surface Area 55.76
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 10.43
Molar Refractivity 178.80

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Created at
15th Mar 2022
Updated at
15th Mar 2022