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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H52O9
Molecular Weight 616.7833
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIMICIFUGOSIDE H1

SMILES

C[C@]([H])(CC(=O)[C@@]1([H])C(C)(C)O1)[C@@]2([H])C(=O)C[C@@]3(C)C4=CC[C@@]5([H])C(C)(C)[C@]([H])(CC[C@]65C[C@@]46[C@]([H])(C[C@]23C)O)O[C@@]7([H])[C@@]([H])([C@]([H])([C@@]([H])(CO7)O)O)O

InChI

InChIKey=PYBFXJMIKJNNAJ-GLWILYKISA-N
InChI=1S/C35H52O9/c1-17(12-18(36)28-31(4,5)44-28)25-19(37)13-32(6)22-9-8-21-30(2,3)24(43-29-27(41)26(40)20(38)15-42-29)10-11-34(21)16-35(22,34)23(39)14-33(25,32)7/h9,17,20-21,23-29,38-41H,8,10-16H2,1-7H3/t17-,20-,21+,23+,24+,25+,26+,27-,28+,29+,32+,33-,34-,35+/m1/s1

HIDE SMILES / InChI

Molecular Formula C35H52O9
Molecular Weight 616.7833
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 0
Optical Activity UNSPECIFIED

Cimicifugoside H1 is biogenetically key compounds of Cimicifugae Rhizoma. In China, the rhizomes of C. foetida L. are used to treat some symptoms, such as headache, toothache, mouth ulcers, and sore throat. Cimicifugoside H1 is a major constituent of Cimicifuga foetida L. extract with 23-epi-26-deoxyactein, cimigenolxyloside, and 25-O-acetylcimigenoside present at lower levels (the percentage 21.2%, 1.6%, 2.9% and 1.1%) but systemic exposure to 23-epi-26-deoxyactein, cimigenolxyloside, and 25-O-acetylcimigenoside following oral administration of the extract of Cimicifuga foetida L. was significantly greater than to Cimicifugoside H1. The low oral bioavailability of Cimicifugoside H1 is probably the result of its poor membrane permeability leading to poor intestinal absorption.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Chemical constituents of original plants of Cimicifugae rhizoma in Chinese medicine].
1996 Nov
Triterpenoid glycoside from Cimicifuga racemosa.
2005 Oct
[Cycloartane triterpenoid of Cimicifuga foetida].
2009 Aug
Simultaneous determination of cimicifugoside H-2, cimicifugoside H-1, 23-epi-26-deoxyactein, cimigenol xyloside and 25-O-acetylcimigenoside in beagle dog plasma by LC-MS/MS.
2012 Mar 25

Sample Use Guides

Rat: 5mg/kg
Route of Administration: Intravenous
Inhibitory activities of cimicifugoside H-1 against Shigella flexneri, Shigella dysenteriae, Shigella sonnei, Mycobacterium tuberculosis, a-hemolytic Streptococcus and Streptococcus pneumoniae was determined by the paper disk diffusion assay on agar plates. The samples were dissolved in chloroform and applied to a paper disk with a syringe (500 mg each disk), respectively. The disks were dried with flow air and put onto agar media inoculated with the testing organism. Inhibition zones were observed after incubation for 10 h at 428C. Cimicifugoside H-1 hasn’t antibacterial activity in the agar diffusion assay.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:20:45 UTC 2021
Edited
by admin
on Sat Jun 26 05:20:45 UTC 2021
Record UNII
C3LF0ZYD3S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIMICIFUGOSIDE H1
Common Name English
CIMICIFUGOSIDE H1 (CONSTITUENT OF BLACK COHOSH) [DSC]
Common Name English
9,19-CYCLOLANOST-7-ENE-16,23-DIONE, 24,25-EPOXY-11-HYDROXY-3-(.BETA.-D- XYLOPYRANOSYLOXY)-, (3.BETA.,11.BETA.,24R)-
Systematic Name English
CIMIFUGOSIDE H-1
Common Name English
CIMICIFUGOSIDE H-1
Common Name English
Code System Code Type Description
CAS
163046-73-9
Created by admin on Sat Jun 26 05:20:45 UTC 2021 , Edited by admin on Sat Jun 26 05:20:45 UTC 2021
PRIMARY
PUBCHEM
15241163
Created by admin on Sat Jun 26 05:20:45 UTC 2021 , Edited by admin on Sat Jun 26 05:20:45 UTC 2021
PRIMARY
FDA UNII
C3LF0ZYD3S
Created by admin on Sat Jun 26 05:20:45 UTC 2021 , Edited by admin on Sat Jun 26 05:20:45 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT