Structure Database (LMSD)

OH OH OH O OH HO HO O O O O OH O O
Common Name
DAT(16:0/24:0(2Me[R],3OH[R],4Me[S],6Me[S]))
Systematic Name
2-O-hexadecanoyl-3-O-(2R,4S,6S-trimethyl-3R-hydroxy-tetracosanoyl)-α,α-trehalose
Synonyms
LM ID
LMSL03000003
Formula
C55H104O14
Exact Mass
Calculate m/z
988.74261
Status
Active (generated by computational methods)
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Saccharolipids [SL]
Acyltrehaloses [SL03]

String Representations

InChiKey (Click to copy)
GMJFLIDPDMRXHA-BPCRLUNHSA-N
InChi (Click to copy)
InChI=1S/C55H104O14/c1-6-8-10-12-14-16-18-20-21-22-24-25-27-29-31-33-35-40(3)37-41(4)46(59)42(5)53(64)68-51-48(61)44(39-57)66-55(69-54-50(63)49(62)47(60)43(38-56)65-54)52(51)67-45(58)36-34-32-30-28-26-23-19-17-15-13-11-9-7-2/h40-44,46-52,54-57,59-63H,6-39H2,1-5H3/t40-,41-,42+,43+,44+,46+,47+,48+,49-,50+,51-,52+,54+,55+/m0/s1
SMILES (Click to copy)
CCCCCCCCCCCCCCCCCC[C@H](C)C[C@H](C)[C@H]([C@@H](C)C(=O)O[C@H]1[C@@H]([C@@H](CO)O[C@@H]([C@@H]1OC(=O)CCCCCCCCCCCCCCC)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mycobacterium tuberculosis (#1773)
Actinomycetia (#1760)
Asymmetric Total Synthesis and Structural Revision of DAT2, an Antigenic Glycolipid from Mycobacterium tuberculosis.,
Angew Chem Int Ed Engl, 2024
Pubmed ID: 38456226
Mycobacterium tuberculosis (#1773)
Actinomycetia (#1760)
Lipidomic analyses of Mycobacterium tuberculosis based on accurate mass measurements and the novel "Mtb LipidDB".,
J Lipid Res, 2011
Pubmed ID: 21285232

Other Databases

PubChem CID
52929840

Calculated Physicochemical Properties

Heavy Atoms 69
Rings 2
Aromatic Rings 0
Rotatable Bonds 44
Van der Waals Molecular Volume 1053.12
Topological Polar Surface Area 226.04
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 14
logP 13.22
Molar Refractivity 275.57

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Created at
-
Updated at
2nd May 2024