Structure Database (LMSD)

Common Name
Squalamine
Systematic Name
3β-N-1-(N-[3-(4-aminobutyl)]- 1,3-diaminopropane)-7α,24R-dihydroxy-5α-cholestane 24-sulfate
Synonyms
LM ID
LMST05050024
Formula
C34H65N3O5S
Exact Mass
Calculate m/z
627.464494
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Other Steroid conjugates [ST0505]
Sulfates [ST0502]
Sterols [ST01]
Cholesterol and derivatives [ST0101]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Squalus acanthias (#7797)
Chondrichthyes (#7777)
Squalamine: an aminosterol antibiotic from the shark,
Proc Natl Acad Sci U S A, 1993
Pubmed ID: 8433993

String Representations

InChiKey (Click to copy)
UIRKNQLZZXALBI-MSVGPLKSSA-N
InChi (Click to copy)
InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-/m1/s1
SMILES (Click to copy)
[C@]12([C@H](O)C[C@@]3([H])C[C@@H](NCCCNCCCCN)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC[C@@H](OS(=O)(=O)O)C(C)C)CC[C@@]21[H])[H]

Other Databases

Wikipedia
Squalamine
KEGG ID
C16841
CHEBI ID
80765
PubChem CID
72495
GuidePharm ID
10861

Calculated Physicochemical Properties

Heavy Atoms 43
Rings 4
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 642.78
Topological Polar Surface Area 133.91
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 8
logP 8.80
Molar Refractivity 177.23

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Created at
-
Updated at
4th Feb 2021