Structure Database (LMSD)

Common Name
Pinnasterol
Systematic Name
2β,3α,20R,22S-tetrahydroxy-cholesta-4,7-dien-6-one
Synonyms
LM ID
LMST01010283
Formula
C27H42O5
Exact Mass
Calculate m/z
446.303225
Sum Composition
ST 27:3;O5
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cholesterol and derivatives [ST0101]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Laurencia (#99900)
Florideophyceae (#2806)
Acetylpinnasterol and pinnasterol, ecdysone-like metabolites, from the marine red alga Laurencia pinnata yamada,
Tetrahedron Letts, 1981

String Representations

InChiKey (Click to copy)
NBEQHHTVOOYUFN-KQLITFJUSA-N
InChi (Click to copy)
InChI=1S/C27H42O5/c1-15(2)6-9-24(31)27(5,32)23-8-7-17-16-12-20(28)19-13-21(29)22(30)14-26(19,4)18(16)10-11-25(17,23)3/h12-13,15,17-18,21-24,29-32H,6-11,14H2,1-5H3/t17-,18-,21-,22-,23-,24-,25-,26+,27+/m0/s1
SMILES (Click to copy)
C12=CC(C3=C[C@H](O)[C@@H](O)C[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@@]1([C@](O)(C)[C@@H](O)CCC(C)C)[H])=O

Other Databases

PubChem CID
52931315

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 462.25
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 4.69
Molar Refractivity 125.71

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Created at
-
Updated at
8th Feb 2021