Structure Database (LMSD)

Common Name
calicoferol A
Systematic Name
(22E)-(8S)-3-hydroxy-9,10-seco-1,3,5(10),22-cholestatetraen-9-one
Synonyms
LM ID
LMST03020605
Formula
C27H40O2
Exact Mass
Calculate m/z
396.30283
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Calicogorgia (#58797)
Anthozoa (#6101)
Calicoferols A and B, Two Novel Secosterols Possessing Brine-Shrimp Lethality from the Gorgonian Calicogorgia sp.,
Chem Letts, 1991

String Representations

InChiKey (Click to copy)
MDPPOIXSNMVHOD-FBPKMIEBSA-N
InChi (Click to copy)
InChI=1S/C27H40O2/c1-18(2)7-6-8-20(4)24-13-14-25-23(26(29)15-16-27(24,25)5)12-10-21-17-22(28)11-9-19(21)3/h6,8-9,11,17-18,20,23-25,28H,7,10,12-16H2,1-5H3/b8-6+/t20-,23+,24-,25+,27-/m1/s1
SMILES (Click to copy)
C1C(C)=C(CC[C@H]2[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC2=O)[C@]([H])(C)/C=C/CC(C)C)C=C(O)C=1

Other Databases

CHEBI ID
187216
LIPIDBANK ID
VVD0114
PubChem CID
9547698

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 1
Rotatable Bonds 7
Van der Waals Molecular Volume 432.06
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.88
Molar Refractivity 120.98

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Created at
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Updated at
18th Jun 2021