Structure Database (LMSD)

OH HO HO O H H H OH O HO O
Common Name
Cucurbitacin C4
Systematic Name
24(R)-methoxy-3β,16α,19,20β,25-pentahydroxycucurbit-5-en-11,22-dione
Synonyms
LM ID
LMST01010514
Formula
C31H50O8
Exact Mass
Calculate m/z
550.35057
Sum Composition
ST 31:3;O8
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)
IKLHOAOHGAPKGH-GTPFPPHWSA-N
InChi (Click to copy)
InChI=1S/C31H50O8/c1-26(2)17-9-11-20-28(5)14-19(33)25(30(7,38)22(35)13-24(39-8)27(3,4)37)29(28,6)15-23(36)31(20,16-32)18(17)10-12-21(26)34/h9,18-21,24-25,32-34,37-38H,10-16H2,1-8H3/t18-,19-,20+,21+,24-,25+,28+,29-,30+,31+/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](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
171119975

Calculated Physicochemical Properties

Heavy Atoms 39
Rings 4
Aromatic Rings
Rotatable Bonds 7
Van der Waals Molecular Volume 557.82
Topological Polar Surface Area 144.52
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 8
logP 4.29
Molar Refractivity 148.56

Admin

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