Paeoniflorin (CED0003695)

Record Information

Version

1.0

Creation Date

2016-05-27 01:38:32 UTC

Update Date

2026-08-22 01:09:13 UTC

Accession Number

CHEM041676

Identification

Common Name

Paeoniflorin

Class

Small Molecule

Description

Paeoniflorin is an organic compound with the formula C23H28O11 and an average molecular weight of 480.46 g/mol. Paeoniflorin belongs to the terpene glycosides, a subclass of prenol lipids within the organic compounds. In industrial applications, it is used as a humectant. The compound is found in or released from 15 recorded sources across several sectors. Within the Electrical & Electronic Equipment sector, it is associated with capacitors, batteries, wires and cables, cell phones, printed circuit boards, and one additional source. It is found in synthetic textiles, carpets and rugs within the textiles, leather & furnishings sector. In the building & construction sector, it is linked to stairs and ramps as well as ladders. Other recorded sources include medical devices in the healthcare, pharmaceuticals & veterinary products sector, lubricants in the energy, oil & gas sector, and food packaging in the food, food processing & cookware sector, along with two more sectors. Exposure to paeoniflorin can occur through oral, inhalation, and touch routes. Regarding its biological activity, there is one recorded protein target for this compound, which acts as a modulator of the Adenosine receptor A1 (ADORA1).

Contaminant Type

PFAS
Phytotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Peoniflorin	MeSH
Peoniflorin sulfonate	MeSH

Chemical Formula

C₂₃H₂₈O₁₁

Average Molecular Mass

480.462 g/mol

Monoisotopic Mass

480.163 g/mol

CAS Registry Number

23180-57-6

IUPAC Name

[(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate

Traditional Name

paeoniflorin

SMILES

[H][C@@]12C[C@@]3(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@]1(COC(=O)C1=CC=CC=C1)[C@@]1([H])O[C@]2(O)C[C@]3(C)O1

InChI Identifier

InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1

InChI Key

YKRGDOXKVOZESV-WRJNSLSBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
Pinane monoterpenoid
Nopinane monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
Furofuran
Oxepane
Meta-dioxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

terpene glycoside (CHEBI:7889 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.32 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-0.39	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.54	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.3 m³·mol⁻¹	ChemAxon
Polarizability	63.3 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-07w9-0409500000-7dd0a95dcaf207ea3b06	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05mk-0907000000-5fcd7c33366a74156839	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052b-2901000000-c84d4aad6ae7cb5be956	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00or-1305900000-625651c159700acc7bec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01di-3917200000-d04b06f7a5cedfb630fd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gka-8927000000-97d89b1eae015c960110	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
3893.0	Log mg/kg	[2200:6900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
7	Pesticides	Agriculture & land management	Not Available
120	Wires and cables	Electrical & Electronic Equipment	Not Available
121	Printed circuit boards	Electrical & Electronic Equipment	Not Available
125	Batteries	Electrical & Electronic Equipment	Not Available
130	Semiconductors	Electrical & Electronic Equipment	Not Available
138	Lubricants	Energy, oil & gas	Not Available
147	Food packaging	Food, food processing & cookware	Not Available
174	Lubricants	Industrial manufacturing & chemical processing	Not Available
234	Medical devices	Healthcare, pharmaceuticals & veterinary products	Not Available
451	Carpets and Rugs	Textiles, leather & furnishings	Not Available
454	Synthetic textiles	Textiles, leather & furnishings	Not Available
490		Personal care & cosmetics	Not Available
492	Cell phones	Electrical & Electronic Equipment	Not Available
493	Capacitors	Electrical & Electronic Equipment	Not Available
498	Ladders	Building & Construction	Not Available
500	Stairs And Ramps	Building & Construction	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Oligo-1,6-glucosidase IMA1	P53051	Saccharomyces cerevisiae S288c	Predicted (SEA)	5.52729
Click to view 3D structure	Type 1 fimbrin D-mannose specific adhesin	P08191	Escherichia coli K-12	Predicted (SEA)	6.92858
Click to view 3D structure	N-acetyllactosaminide alpha-1,3-galactosyltransferase	P50127	Sus scrofa	Predicted (SEA)	4.9045
Click to view 3D structure	Asialoglycoprotein receptor 1	P34927	Mus musculus	Predicted (SEA)	5.0602
Click to view 3D structure	Galectin-3	P17931	Humans	Predicted (SEA)	12.4559
Click to view 3D structure	Lectin	B4EH87	Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))	Predicted (SEA)	8.40772
Click to view 3D structure	Peptidoglycan-N-acetylglucosamine deacetylase	Q8DP63	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Predicted (SEA)	5.0602
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	743.771
Click to view 3D structure	Galectin-9	O00182	Humans	Predicted (SEA)	11.6774
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	P54751	Mus musculus	Predicted (SEA)	4.35956
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	995.847
Click to view 3D structure	Beta-1,4-galactosyltransferase 1	P08037	Bos taurus	Predicted (SEA)	9.03051
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	660.784
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	1084.83
Click to view 3D structure	Sodium/glucose cotransporter 1	P13866	Humans	Predicted (SEA)	18.061
Click to view 3D structure	Adenosine kinase	P55263	Humans	Predicted (SEA)	96.4552
Click to view 3D structure	CD44 antigen	P16070	Humans	Predicted (SEA)	5.3716
Click to view 3D structure	CD44 antigen	P15379	Mus musculus	Predicted (SEA)	5.3716
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	1864.72
Click to view 3D structure	Adenosine kinase	P9WID4	Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)	Predicted (SEA)	34.5651
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	766.348
Click to view 3D structure	Killer cell lectin-like receptor subfamily B member 1A	P27471	Rattus norvegicus	Predicted (SEA)	5.3716
Click to view 3D structure	Solute carrier family 28 member 3	Q9HAS3	Humans	Predicted (SEA)	33.0859
Click to view 3D structure	Solute carrier family 2, facilitated glucose transporter member 1	P11167	Rattus norvegicus	Predicted (SEA)	8.48557
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	826.914