Structure Database (LMSD)

Common Name
Stigmasterol
Systematic Name
stigmasta-5,22E-dien-3β-ol
Synonyms
LM ID
LMST01040123
Formula
C29H48O
Exact Mass
Calculate m/z
412.370515
Sum Composition
ST 29:2;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Stigmasterols and C24-ethyl derivatives [ST0104]

Biological Context

Stigmasterol is a natural plant sterol that can be isolated from certain seed oils and herbs, including those used for therapeutic purposes.1,2 Dietary consumption of phytosterols, including stigmasterol, may have beneficial health effects in adults, particularly against cancer and ulceration.3,4,5 Alternatively, phytosterols may contribute to inflammation and intestinal failure-associated liver disease in young individuals.6

This information has been provided by Cayman Chemical

References

1. Ali, H., Dixit, S., Ali, D., et al. Isolation and evaluation of anticancer efficacy of stigmasterol in a mouse model of DMBA-induced skin carcinoma. Drug. Des. Devel. Ther. 9, 2793-2800 (2015).
2. Awad, A.B., and Fink, C.S. Phytosterols as anticancer dietary components: Evidence and mechanism of action. J. Nutr. 130, 2127-2130 (2000).
3. Ganie, S.A., and Yadav, S.S. Holoptelea integrifolia (Roxb.) Planch: A review of its ethnobotany, pharmacology, and phytochemistry. Biomed. Res. Int. 2014(401213), 1-12 (2014).
4. Mo, S., Dong, L., Hurst, J., et al. Quantitative analysis of phytosterols in edible oils using APCI liquid chromatography-tandem mass spectrometry. Lipids 48(9), 949-956 (2013).
5. Mutanen, A., Nissinen, M.J., Lohi, J., et al. Serum plant sterols, cholestanol, and cholesterol precursors associate with histological liver injury in pediatric onset intestinal failure. Am. J. Clin. Nutr. 100(4), 1085-1094 (2014).
6. Tovey, F.I. Role of dietary phospholipids and phytosterols in protection against peptic ulceration as shown by experiments on rats. World J. Gastroenterol. 21(5), 1377-1384 (2015).

String Representations

InChiKey (Click to copy)
HCXVJBMSMIARIN-PHZDYDNGSA-N
InChi (Click to copy)
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@@H](CC)C(C)C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

Wikipedia
Stigmasterol
KEGG ID
C05442
HMDB ID
HMDB0000937
CHEBI ID
28824
LIPIDBANK ID
SST9068
PubChem CID
5280794
Cayman ID
18079

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 464.33
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 8.09
Molar Refractivity 128.63

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Updated at
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