Structure Database (LMSD)

Common Name
Toporoside C
Systematic Name
N-((28-O-β-D-glucuronopyranosyl)-11,16-dioxo-2S-methoxy-5Z,19Z-octacosadienoyl)-dopamine
Synonyms
LM ID
LMFA08020392
Formula
C43H67NO13
Exact Mass
Calculate m/z
805.461244
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl amines [FA0802]
Fatty Acids and Conjugates [FA01]
Oxo fatty acids [FA0106]
Methoxy fatty acids [FA0108]
Unsaturated fatty acids [FA0103]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Myxillidae (#118318)
Demospongiae (#6042)
Toporosides A and B, Cyclopentenyl-Containing ω-Glycosylated Fatty Acid Amides, and Toporosides C and D from the Northwestern Pacific Marine Sponge Stelodoryx toporoki.,
J Nat Prod, 2022
Pubmed ID: 35377646

String Representations

InChiKey (Click to copy)
XSFUIKFWSIGOPC-XVRDXBJXSA-N
InChi (Click to copy)
InChI=1S/C43H67NO13/c1-55-36(41(52)44-28-27-31-25-26-34(47)35(48)30-31)24-16-12-8-7-11-15-21-33(46)23-18-17-22-32(45)20-14-10-6-4-2-3-5-9-13-19-29-56-43-39(51)37(49)38(50)40(57-43)42(53)54/h6,8,10,12,25-26,30,36-40,43,47-51H,2-5,7,9,11,13-24,27-29H2,1H3,(H,44,52)(H,53,54)/b10-6-,12-8-/t36-,37-,38-,39+,40-,43+/m0/s1
SMILES (Click to copy)
C([C@@H](OC)CC/C=C\CCCCC(=O)CCCCC(=O)CC/C=C\CCCCCCCCO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(=O)O)O1)(=O)NCCC1=CC(O)=C(O)C=C1

Other Databases

PubChem CID
168280045

Calculated Physicochemical Properties

Heavy Atoms 57
Rings 2
Aromatic Rings 1
Rotatable Bonds 32
Van der Waals Molecular Volume 818.35
Topological Polar Surface Area 231.45
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 14
logP 7.63
Molar Refractivity 217.62

Admin

Created at
20th Apr 2022
Updated at
20th Apr 2022