Structure Database (LMSD)

Common Name
Meliasanine B
Systematic Name
(3R,5R,9R,10R,13S,14S,16S,17S,20S) methyl 6-oxo-3,16-dihydroxy-tirucalla-7,24-dien-20-oate
Synonyms
LM ID
LMPR0106090004
Formula
C31H48O5
Exact Mass
Calculate m/z
500.350175
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C30 isoprenoids (triterpenes) [PR0106]
Tirucallane/euphane triterpenoids [PR010609]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Melia azedarach var. toosendan (#71608)
Magnoliopsida (#3398)
Meliasanines A-L, tirucallane-type triterpenoids from Melia toosendan with anti-inflammatory properties via NF-κB signaling pathway.,
Phytochemistry, 2024
Pubmed ID: 38901624

String Representations

InChiKey (Click to copy)
NDLJKDOVALQCTN-DLTDCGHESA-N
InChi (Click to copy)
InChI=1S/C31H48O5/c1-18(2)10-9-11-19(27(35)36-8)25-23(33)17-31(7)21-16-22(32)26-28(3,4)24(34)13-14-29(26,5)20(21)12-15-30(25,31)6/h10,16,19-20,23-26,33-34H,9,11-15,17H2,1-8H3/t19-,20-,23-,24+,25+,26-,29+,30-,31+/m0/s1
SMILES (Click to copy)
C1C[C@]2(C)[C@@]3([H])CC[C@@]4(C)[C@]([H])([C@@H](C(OC)=O)CC/C=C(\C)/C)[C@@H](O)C[C@]4(C)C3=CC(=O)[C@@]2([H])C(C)(C)[C@@H]1O

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 4
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 528.81
Topological Polar Surface Area 83.83
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 6.21
Molar Refractivity 141.96

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Created at
26th Jun 2024
Updated at
26th Jun 2024