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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H56O10
Molecular Weight 660.836
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 23-EPI-26-DEOXYACTEIN

SMILES

C[C@]1([H])C[C@]2([C@@]3([H])[C@@](C)(CO2)O3)O[C@@]4([H])C[C@@]5(C)[C@]6([H])CC[C@@]7([H])C(C)(C)[C@]([H])(CC[C@]87C[C@@]68C[C@]([H])([C@]5(C)[C@@]14[H])OC(=O)C)O[C@@]9([H])[C@@]([H])([C@]([H])([C@@]([H])(CO9)O)O)O

InChI

InChIKey=GCMGJWLOGKSUGX-WUHYQCRDSA-N
InChI=1S/C37H56O10/c1-18-12-37(30-33(6,47-30)17-43-37)46-21-13-32(5)23-9-8-22-31(3,4)24(45-29-28(41)27(40)20(39)15-42-29)10-11-35(22)16-36(23,35)14-25(44-19(2)38)34(32,7)26(18)21/h18,20-30,39-41H,8-17H2,1-7H3/t18-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30-,32+,33-,34-,35-,36+,37-/m1/s1

HIDE SMILES / InChI

Molecular Formula C37H56O10
Molecular Weight 660.836
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 17 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14758092

23-epi-26-deoxyactein (formerly 27-deoxyactein), is the most abundant triterpene glycosides of black cohosh, inhibits growth of the MCF7 human breast cancer cells and induces cell cycle arrest at G1 and might eventually be useful in the prevention or treatment of breast cancer. Also was investigated the mechanism of action of 23-epi-26-deoxyactein, and was shown that 23-epi-26-deoxyactein decreased IFNγ-induced iNOS mRNA and NO production in brain microglial cells.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: nitric oxide production
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of 23-epi-26-deoxyactein in women after oral administration of a standardized extract of black cohosh.
2010 Feb
Patents

Patents

Sample Use Guides

Single doses of black cohosh extract containing 1.4, 2.8, or 5.6 mg of 23-epi-26-deoxyactein were administered to 15 healthy, menopausal women
Route of Administration: Oral
BV-2 murine microglia cells stimulated for 18 hours with LPS produced 29 ± 6 μM NO. 30 μg/ml 23-epi-26-deoxyactein had no effect on NO production, but inhibited IFNγ-induced NO production in a dose dependent fashion up to 14%, with a slight increase observed at the lower doses (0.3 μg/ml) of 23-epi-26 deoxyactein. 30 μg/ml 23-epi-26-deoxyactein slightly stimulated LPS-induced NO.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:56:27 UTC 2021
Edited
by admin
on Sat Jun 26 12:56:27 UTC 2021
Record UNII
2A97XP2V7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
23-EPI-26-DEOXYACTEIN
Common Name English
23-EPI-26-DEOXYACTEIN (CONSTITUENT OF BLACK COHOSH) [DSC]
Common Name English
23-EPI-26-DEOXYACTEIN [USP-RS]
Common Name English
.BETA.-D-XYLOPYRANOSIDE, (3.BETA.,12.BETA.,16.BETA.,23S,24R,25R)-12-(ACETYLOXY)-16,23:23,26: 24,25-TRIEPOXY-9,19-CYCLOLANOSTAN-3-YL
Systematic Name English
Code System Code Type Description
EPA CompTox
501938-01-8
Created by admin on Sat Jun 26 12:56:27 UTC 2021 , Edited by admin on Sat Jun 26 12:56:27 UTC 2021
PRIMARY
CAS
501938-01-8
Created by admin on Sat Jun 26 12:56:27 UTC 2021 , Edited by admin on Sat Jun 26 12:56:27 UTC 2021
PRIMARY
PUBCHEM
21668683
Created by admin on Sat Jun 26 12:56:27 UTC 2021 , Edited by admin on Sat Jun 26 12:56:27 UTC 2021
PRIMARY
FDA UNII
2A97XP2V7I
Created by admin on Sat Jun 26 12:56:27 UTC 2021 , Edited by admin on Sat Jun 26 12:56:27 UTC 2021
PRIMARY
USP_CATALOG
1171207
Created by admin on Sat Jun 26 12:56:27 UTC 2021 , Edited by admin on Sat Jun 26 12:56:27 UTC 2021
PRIMARY USP-RS
Related Record Type Details
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