Structure Database (LMSD)

H OH HO HO O H H O O O O HO
Common Name
Cucurbitacin C3
Systematic Name
24(R)-ethoxy-25-acetyloxy-3β,16α,19,20β-tetrahydroxycucurbit-5-en-11,22-dione
Synonyms
LM ID
LMST01010513
Formula
C34H54O9
Exact Mass
Calculate m/z
606.376785
Sum Composition
ST 34:4;O9
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

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

String Representations

InChiKey (Click to copy)
CZXKYBFPVQUECF-XMMRPQHUSA-N
InChi (Click to copy)
InChI=1S/C34H54O9/c1-10-42-27(30(5,6)43-19(2)36)15-25(39)33(9,41)28-22(37)16-31(7)23-13-11-20-21(12-14-24(38)29(20,3)4)34(23,18-35)26(40)17-32(28,31)8/h11,21-24,27-28,35,37-38,41H,10,12-18H2,1-9H3/t21-,22-,23+,24+,27-,28+,31+,32-,33+,34+/m1/s1
SMILES (Click to copy)
[C@@]12(CO)C(=O)C[C@]3(C)[C@]([H])([C@H](O)C[C@@]3(C)[C@]1([H])CC=C1C(C)(C)[C@H](CC[C@@]21[H])O)[C@](O)(C)C(=O)C[C@@H](OCC)C(OC(C)=O)(C)C

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cucumis sativus (#3659)
Magnoliopsida (#3398)
Identification of seven undescribed cucurbitacins in Cucumis sativus (cucumber) and their cytotoxic activity.,
Phytochemistry, 2022
Pubmed ID: 35182783

Other Databases

PubChem CID
171119974

Calculated Physicochemical Properties

Heavy Atoms 43
Rings 4
Aromatic Rings
Rotatable Bonds 10
Van der Waals Molecular Volume 615.87
Topological Polar Surface Area 150.59
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 5.53
Molar Refractivity 163.22

Admin

Created at
22nd Apr 2022
Updated at
22nd Apr 2022