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[5-Hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate

HCID 3512643
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Basic information

CAS
11027-63-7
Standard SMILES
O=C(OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O)C3O)C12)c1ccc(O)cc1
InChIKey
GLACGTLACKLUJX-UHFFFAOYSA-N
Molecular formula
C22H26O11
Average molar mass
466.4 g/mol
Monoisotopic mass
466.14751164

Overview

Agnoside has been reported in Vitex negundo, Vitex lucens, and Vitex agnus-castus with data available.

Names & identifiers

Preferred name
[5-Hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
IUPAC
[5-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
English name
Agnuside
Molecular formula
C22H26O11
Molecular weight
466.44

Names & synonyms

Agnuside [M+H]+[5-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoateVitex OilAgnusidAgnosideAGNUSIDEOyster oilAGNUSIDE(P)Buddlejoside Achasteberry oilAgnuside (25 mg)AGNUSIDE WITH HPLC

Database identifiers

CAS
11027-63-7
PubChem CID
3512643

Properties

Computed structural properties

XLogP
-1.1
Topological polar surface area
175 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
11
Rotatable bonds
7
Heavy atoms
33
Formal charge
0
Complexity
747

Experimental & physicochemical properties

Melting Point146 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
146 ℃ · 146℃
Boiling point
785.5 · 785.5±60.0 °C(Predicted)
Density
1.59 · 1.59±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
DMSO, Methanol
pka
8.14 · 8.14±0.15(Predicted)
form
Solid
color
Yellow
optical activity
-98 · [α]/D -98.0±5°, c = 0.1 in ethanol
BRN
4925795 · 4925795
Major Application
metabolomicsvitamins, nutraceuticals, and natural products
InChIKey
GLACGTLACKLUJX-QNAXTHAFSA-N

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
hs_code
29329990
risk_code
36
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P301+P312+P330

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Applications · 1 item

UsesAgnuside is an known iridoid glycoside found in Vitex herbs or plants. Agnuside have been used in various applications including in the treatment of premenstrual syndrome and regulation of menopause s ymptoms. This is mainly due to the fact that Agnuside exhibits estrogen-like activities as it interacts with estrogen receptors (ER-alpha) and estrogen receptor-regulated pregesterone receptors. Recen t studies have also evaluated Agnuside for the probable mechanism of anti-arthritic activity, which suggested the possible development of Agnuside as a therapeutic agent in the treatment of arthritis by the modulation of the host immune response.

Additional notes · 1 item

DefinitionChEBI: Agnuside is a benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. It has a role as a plant metabolite, an anti-inflammatory agent, a pro-angiogenic agent and a cyclooxygenase 2 inhibitor. It is a terpene glycoside, an iridoid monoterpenoid, a benzoate ester, a member of phenols, a beta-D-glucoside, a cyclopentapyran and a monosaccharide derivative. It is functionally related to an aucubin.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
SMILES
[C@]12([H])C(COC(=O)C3=CC=C(O)C=C3)=C[C@H](O)[C@@]1([H])C=CO[C@@H]2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O |&1:0,15,17,22,24,25,27,28,30,r|
LogP
-1.24 · -1.240 (est)
FDA UNII
24 Q0OT9G · JB24Q0OT9G
UNSPSC Code
85151701 · 85151701
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
301 · P301+P312+P330
Hazard Codes
Xi
Risk Statements
36 · 36
Safety Statements
26 · 26
WGK Germany
3 · 3
HS Code
29329990 · 29329990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral