Structure Database (LMSD)

Common Name
Cucurbitacin C6
Systematic Name
25-acetyloxy-3β,16α,20β-trihydroxy-5β,19β-epoxy-cucurbit-6-en-11,22-dione
Synonyms
LM ID
LMST01010516
Formula
C32H48O8
Exact Mass
Calculate m/z
560.33492
Sum Composition
ST 32:5;O8
Status
Active
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
Cucumis sativus (#3659)
Magnoliopsida (#3398)
Identification of seven undescribed cucurbitacins in Cucumis sativus (cucumber) and their cytotoxic activity.,
Phytochemistry, 2022
Pubmed ID: 35182783

String Representations

InChiKey (Click to copy)
MFMXRVNIDXBHHV-DSZIFTQBSA-N
InChi (Click to copy)
InChI=1S/C32H48O8/c1-18(33)40-26(2,3)13-12-23(36)30(8,38)25-19(34)15-28(6)20-11-14-32-21(9-10-22(35)27(32,4)5)31(20,17-39-32)24(37)16-29(25,28)7/h11,14,19-22,25,34-35,38H,9-10,12-13,15-17H2,1-8H3/t19-,20+,21+,22+,25+,28+,29-,30+,31-,32-/m1/s1
SMILES (Click to copy)
[C@@]123CO[C@@]4(C=C[C@@]1([H])[C@]1(C)C[C@H]([C@]([H])([C@](O)(C)C(=O)CCC(OC(=O)C)(C)C)[C@]1(CC2=O)C)O)C(C)(C)[C@H](CC[C@@]34[H])O

Other Databases

PubChem CID
171119977

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 5
Aromatic Rings
Rotatable Bonds 7
Van der Waals Molecular Volume 560.12
Topological Polar Surface Area 132.43
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 5.25
Molar Refractivity 149.97

Admin

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