Structure Database (LMSD)

Common Name
Hecogenin
Systematic Name
(25R)-12-oxo-spirostan-3β-ol
Synonyms
  • (25R)-3beta-hydroxy-5alpha-spirostan-12-one
LM ID
LMST01080014
Formula
Exact Mass
Calculate m/z
430.30831
Sum Composition
Status
Curated

Classification

Biological Context

Hecogenin is a natural steroid sapogenin with diverse biological activities that was originally isolated from A. sisalana and has been used in the synthesis of steroids.1 It has antioxidant, anti-inflammatory, antiproliferative, and neuroprotective properties.2,3,4,5 Hecogenin (10 μM) decreases superoxide anion formation induced by N-Formyl-Met-Leu-Phe (fMLP) in rat neutrophils by 23.6%.2 It also inhibits myeloperoxidase (MPO) release from human neutrophils activated by phorbol 12-myristate 13-acetate (PMA) when used at a concentration of 1 μg/ml.3 Hecogenin inhibits proliferation of the breast cancer cell lines MDA-MB-231, MDA-MB-468, MCF-10A, MCF-7, T47D, BT474, and SK-BR-3 (IC50s = 28.7-38.2 μM).4 It decreases the number of glutamate-induced TUNEL-positive primary rat spinal motor neurons by 11% when used at a concentration of 1 μM.5 In vivo, hecogenin (15 mg/kg) decreases the mucosal lesion area of ethanol-induced gastric ulceration in mice.3 It also decreases tumor volume in an MDA-MB-231 human breast cancer mouse xenograft model when administered at a dose of 10 mg/kg three times per week.4

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Agave americana (#39510)
Magnoliopsida (#3398)
Steroid saponins,
Phytochemistry, 1982

String Representations

InChiKey (Click to copy)
QOLRLLFJMZLYQJ-LOBDNJQFSA-N
InChi (Click to copy)
InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC(=O)[C@]4(C)[C@H]5[C@@H]([C@]6(O[C@H]5C[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@@H](O)C1)CC[C@@H](C)CO6)C

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 6
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 434.02
Topological Polar Surface Area 59.90
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 6.12
Molar Refractivity 120.14

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Updated at
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