Structure Database (LMSD)

Common Name
Taccalonolide A
Systematic Name
(2R,3R,5S)-2-(1-hydroxy-1-methyl-ethyl)-5-[(3R,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]tetrahydropyran-3-ol
Synonyms
  • AC1L9BGV
  • CHEMBL1821838
LM ID
LMST01160016
Formula
C36H46O14
Exact Mass
Calculate m/z
702.28876
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Withanolides and derivatives [ST0116]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Tacca plantaginea (#44982)
Magnoliopsida (#3398)
Steroidal bitter principles from tacca plantaginea structures of taccalonolide A and B,
Tetrahedron Letts, 1987

String Representations

InChiKey (Click to copy)
PTTJLTMUKRRHAT-VJAKQJMOSA-N
InChi (Click to copy)
InChI=1S/C36H46O14/c1-12-10-19-35(8,36(9,44)32(43)50-19)24-21(12)34(7)22(28(24)45-13(2)37)20-23(29(46-14(3)38)31(34)48-16(5)40)33(6)17(25(41)26(20)42)11-18-27(49-18)30(33)47-15(4)39/h10,12,17-18,20-24,26-31,42,44H,11H2,1-9H3/t12-,17-,18+,20+,21+,22-,23-,24+,26-,27+,28-,29+,30+,31+,33+,34-,35+,36-/m1/s1
SMILES (Click to copy)
O1[C@H]2C[C@]3([H])C([C@@H]([C@]4([H])[C@]([H])([C@@H]([C@@H]([C@@]5([C@@]6([H])[C@H](C)C=C7[C@]([C@]6([H])[C@H](OC(=O)C)[C@]54[H])(C)[C@@](C)(C(=O)O7)O)C)OC(=O)C)OC(C)=O)[C@@]3(C)[C@H]([C@@H]12)OC(C)=O)O)=O

Other Databases

KEGG ID
C08635
CHEBI ID
9388
PubChem CID
441685

Calculated Physicochemical Properties

Heavy Atoms 50
Rings 7
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 649.42
Topological Polar Surface Area 203.63
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 14
logP 3.70
Molar Refractivity 169.83

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Created at
-
Updated at
10th Jul 2021