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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H44O5
Molecular Weight 472.6567
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HECOGENIN ACETATE

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@H](CC[C@]5(C)[C@@]4([H])CC(=O)[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2)OC(C)=O

InChI

InChIKey=CVKZWRTYHCDWTE-RSEFXUKDSA-N
InChI=1S/C29H44O5/c1-16-8-11-29(32-15-16)17(2)26-24(34-29)13-23-21-7-6-19-12-20(33-18(3)30)9-10-27(19,4)22(21)14-25(31)28(23,26)5/h16-17,19-24,26H,6-15H2,1-5H3/t16-,17+,19+,20+,21-,22+,23+,24+,26+,27+,28-,29-/m1/s1

HIDE SMILES / InChI
Molecular Formula C29H44O5
Molecular Weight 472.6567
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Hecogenin acetate is the acetylated form of Hecogenin, a naturally occurring sapogenin present in the leaves of plants from the Agave genus. It has been found to have antinociceptive activity in mice and has also been investigated as an anti-cancer agent in vitro. Hecogenin appears to exert its anticancer influence by modulating the ERK1/2 signal cascade and activates opioid receptors to influence nocioception.

CNS Activity

CNS Active
3913
Curator's Comment: referenced study was conducted in mouse

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
2013 Apr 26
Hecogenin acetate inhibits reactive oxygen species production and induces cell cycle arrest and senescence in the A549 human lung cancer cell line.
2014
Evidence for the involvement of spinal cord-inhibitory and cytokines-modulatory mechanisms in the anti-hyperalgesic effect of hecogenin acetate, a steroidal sapogenin-acetylated, in mice.
2014 Jun 19
Natural Products as Chemopreventive Agents by Potential Inhibition of the Kinase Domain in ErbB Receptors.
2017 Feb 17
Patents

Patents

FR2815256A1
1
US20030235599A1
1
US20040197416A1
1
US2774714A
1
US2827456A
1
US3303186A
1
US3935194A
1
US6150336A
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: the referenced study was conducted in mouse
Hecogenin acetate was administered to mice via intraperitoneal injection in doses between 5 - 40 mg/kg. Mouse motor performance was evaluated by using the tail flick rotarod test. Dosing with Hecogenin acetate produced an antinociception effect in a dose-dependent manner. The antinociception was prevented by naloxone a non-specific opioid receptor antagonist as well as several specific receptor antagonists.
Route of Administration: Intraperitoneal
In Vitro Use Guide
A549 non-small lung cancer cells were exposed to different concentrations of hecogenin acetate. Hecogenin acetate significantly inhibited increase in intracellular reactive species production induced by H2O2. Hecogenin acetate blocked ERK1/2 phosphorylation and inhibited the increase in MMP-2. The treatment induced G0/G1 cell cycle arrest at 75 and 100 micro M of hecogenin acetate.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:03:03 GMT 2023
Edited
by admin
on Sat Dec 16 10:03:03 GMT 2023
Record UNII
5K0WKD513R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HECOGENIN ACETATE
Common Name English
SPIROSTAN-12-ONE, 3-(ACETYLOXY)-, (3.BETA.,5.ALPHA.,25R)-
Systematic Name English
(22R,25R)-12-OXO-28-OXA-5.ALPHA.-SPIROSOLANE-3.BETA.-OL ACETATE
Systematic Name English
NSC-15489
Code English
12-OXO-5-.ALPHA.-SPIROSTAN-3-.BETA.-YL ACETATE
Systematic Name English
3.BETA.-ACETOXY-5.ALPHA.-SPIROSTAN-12-ONE
Common Name English
(3.BETA.,5.ALPHA.,25R)-12-OXOSPIROSTAN-3-YL ACETATE
Systematic Name English
J195.206D
Code English
5.ALPHA.,25D-SPIROSTAN-12-ONE, 3.BETA.-HYDROXY-, ACETATE
Systematic Name English
(-)-HECOGENIN ACETATE
Common Name English
(22R,25R)-3.BETA.-ACETOXY-5.ALPHA.-SPIROSTANE-12-ONE
Systematic Name English
5.ALPHA.-SPIROSTAN-12-ONE, 3.BETA.-HYDROXY-, ACETATE, (25R)-
Systematic Name English
Code System Code Type Description
EVMPD
SUB116125
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
SMS_ID
100000142189
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
PUBCHEM
101906
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
FDA UNII
5K0WKD513R
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
CAS
915-35-5
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID90919692
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-021-7
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
NSC
15489
Created by admin on Sat Dec 16 10:03:03 GMT 2023 , Edited by admin on Sat Dec 16 10:03:03 GMT 2023
PRIMARY
NIH
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