Structure Database (LMSD)

Common Name
Dolicholide
Systematic Name
2α,3α,22R,23R-tetrahydroxy-6,7-seco-ergost-24(28)-en-6,7-lactone
Synonyms
  • 2alpha,3alpha,22R,23R-tetrahydroxy-homo-7-oxa-5alpha-ergost-24(28)-en-6-one
LM ID
LMST01140004
Formula
C28H46O6
Exact Mass
Calculate m/z
478.32944
Sum Composition
ST 28:2;O6
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Brassinolides and derivatives [ST0114]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Lablab purpureus (#35936)
Magnoliopsida (#3398)
A new steroidal lactone with plant growth-regulatory activity from Dolichos lablab seed,
Tetrahedron Letts, 1982

String Representations

InChiKey (Click to copy)
PPFRJNLKWADOTL-WOGJWQOOSA-N
InChi (Click to copy)
InChI=1S/C28H46O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14,16-25,29-32H,3,7-13H2,1-2,4-6H3/t16-,17-,18+,19-,20-,21+,22-,23+,24+,25+,27+,28+/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)[C@@H](O)[C@H](O)C(=C)C(C)C)CC[C@@]4([H])[C@]3([H])COC(=O)[C@@]2([H])C[C@H](O)[C@@H]1O

Other Databases

CHEBI ID
166786
PubChem CID
11038144

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 4
Aromatic Rings
Rotatable Bonds 5
Van der Waals Molecular Volume 490.98
Topological Polar Surface Area 109.29
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 4.74
Molar Refractivity 132.03

Admin

Created at
20th Dec 2022
Updated at
20th Dec 2022