Paeoniflorin

Details

• Internal ID: 3aee401f-2145-4763-a51c-1ab379555c13
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• 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
• InChI: 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
• Popularity: 952 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₁
• Molecular Weight: 480.50 g/mol
• Exact Mass: 480.16316171 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.36
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 23180-57-6
• Peoniflorin
• 21AIQ4EV64
• DTXSID2042648
• [(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
• NSC-178886
• ((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
• RefChem:45627
• DTXCID401478399
• 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd) pentalen-1a(2H)-yl-beta-D-glucopyranoside
• 245-476-2
• Paeonia moutan
• MFCD00869331
• NSC 178886
• paeoniflorine
• ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methyl benzoate
• b-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl
• Paeoniflorin (>80%)
• C23H28O11
• UNII-21AIQ4EV64
• CCRIS 6494
• NSC178886
• s2410
• YKRGDOXKVOZESV-WRJNSLSBSA-N
• .BETA.-D-GLUCOPYRANOSIDE, (1AR,2S,3AR,5R,5AR,5BS)-5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL
• .beta.-D-Glucopyranoside, (1aR,2S,3aR,5R,5aR,5bS)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl
• EINECS 245-476-2
• Paeoniflorin (Standard)
• PAEONIFLORIN [USP-RS]
• SCHEMBL549033
• AC1L9D12
• CHEBI:7889
• orb1306020
• CHEMBL4303209
• HY-N0293R
• Paeoniflorin, analytical standard
• Paeoniflorin, >=98% (HPLC)
• GLXC-13167
• HMS3884D17
• HY-N0293
• CP0062
• MSK157242
• AKOS025311455
• CCG-269549
• MP08290
• AS-12193
• beta-D-Glucopyranoside, (1aS,2R,3aR,5R,5aR,5bS)-5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl
• NS00027374
• C09959
• AB01566855_01
• 180P576
• Q7124104
• BRD-K83631119-001-02-1
• ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methylbenzoate
• .BETA.-D-GLUCOPYRANOSIDE, 5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL, (1AR-(1A.ALPHA.,2.BETA.,3A.ALPHA.,5.ALPHA.,5A.ALPHA.,5B.ALPHA.))-
• [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
• [hydroxy-methyl-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]methyl benzoate
• 5b-((Benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl-beta-D-glucopyranoside
• 9[(Benzoyioxy)methyl]-1-(?-D-glucopyranosyloxy)-4,8-epoxy-6-methyl-7-oxaticyclo[4,3,0,0]nonane
• beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, (1aR-(1a-alpha,2-beta,3a-alpha,5-alpha,5a-alpha,5b-alpha))-
• beta-d-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6700	67.00%
Caco-2	-	0.8220	82.20%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5798	57.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5449	54.49%
P-glycoprotein inhibitior	-	0.6521	65.21%
P-glycoprotein substrate	-	0.7828	78.28%
CYP3A4 substrate	+	0.6660	66.60%
CYP2C9 substrate	-	0.8039	80.39%
CYP2D6 substrate	-	0.8544	85.44%
CYP3A4 inhibition	-	0.8545	85.45%
CYP2C9 inhibition	-	0.9006	90.06%
CYP2C19 inhibition	-	0.7995	79.95%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.8834	88.34%
CYP2C8 inhibition	+	0.5730	57.30%
CYP inhibitory promiscuity	-	0.9467	94.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5848	58.48%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9506	95.06%
Skin irritation	-	0.7427	74.27%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3963	39.63%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.8111	81.11%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.3551	35.51%
Estrogen receptor binding	+	0.8184	81.84%
Androgen receptor binding	+	0.7230	72.30%
Thyroid receptor binding	+	0.6528	65.28%
Glucocorticoid receptor binding	+	0.5504	55.04%
Aromatase binding	+	0.7941	79.41%
PPAR gamma	+	0.7787	77.87%
Honey bee toxicity	-	0.8146	81.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9390	93.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.89%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.08%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	93.68%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.43%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.03%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.29%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.86%	94.08%
CHEMBL226	P30542	Adenosine A1 receptor	84.69%	95.93%
CHEMBL5028	O14672	ADAM10	84.03%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	83.52%	94.73%
CHEMBL2581	P07339	Cathepsin D	83.26%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.10%	94.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.91%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.03%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.71%	99.23%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Cnidium silaifolium
• Galium aegeum
• Paeonia anomala
• Paeonia clusii
• Paeonia delavayi
• Paeonia emodi
• Paeonia lactiflora
• Paeonia obovata
• Paeonia peregrina
• Paeonia suffruticosa
• Paeonia tenuifolia
• Pavonia alba
• Salvinia molesta

Cross-Links

• PubChem: 442534
• NPASS: NPC56594
• LOTUS: LTS0030790
• wikiData: Q7124104