Structure Database (LMSD)

Common Name
Brainesteroside C
Systematic Name
3-O-(β-D-glucopyranosyl)-2β,3β,6,20,22R-pentahydroxy-cholest-5,8,14-trien-7-one
Synonyms
  • 25-deoxycalonysterone 3-O-beta-D-glucopyranoside
LM ID
LMST01010434
Formula
C33H50O11
Exact Mass
Calculate m/z
622.335315
Sum Composition
ST 27:4;O6;Hex
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cholesterol and derivatives [ST0101]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Brainea insignis (#120713)
Polypodiopsida (#241806)
Phytoecdysteroids from the rhizomes of Brainea insignis.,
Phytochemistry, 2010
Pubmed ID: 20347104

String Representations

InChiKey (Click to copy)
UVTRNQDEASOAEI-CRTQUAMDSA-N
InChi (Click to copy)
InChI=1S/C33H50O11/c1-15(2)6-9-23(36)33(5,42)22-8-7-16-24-17(10-11-31(16,22)3)32(4)13-19(35)20(12-18(32)25(37)27(24)39)43-30-29(41)28(40)26(38)21(14-34)44-30/h7,15,19-23,26,28-30,34-38,40-42H,6,8-14H2,1-5H3/t19-,20+,21+,22-,23+,26+,28-,29+,30+,31-,32+,33+/m0/s1
SMILES (Click to copy)
C1[C@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CC2=C(O)C(=O)C3=C(CC[C@]4(C3=CC[C@]4([H])[C@](O)(C)[C@H](O)CCC(C)C)C)[C@]21C

Other Databases

PubChem CID
101514324

Calculated Physicochemical Properties

Heavy Atoms 44
Rings 5
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 603.79
Topological Polar Surface Area 199.44
Hydrogen Bond Donors 8
Hydrogen Bond Acceptors 11
logP 4.18
Molar Refractivity 163.01

Admin

Created at
30th Nov 2020
Updated at
30th Nov 2020