Natural Product (NP) Details

General Information of the NP (ID: NP3185)
Name
Paeoniflorin
Synonyms
Paeoniflorin; Peoniflorin; 23180-57-6; Paeonia moutan; Paeony root; NSC 178886; UNII-21AIQ4EV64; 21AIQ4EV64; C23H28O11; ((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; paeoniflorine; paeoniflorin;; Peoniflorin;; CCRIS 6494; MFCD00869331; NSC178886; EINECS 245-476-2; SCHEMBL549033; CHEBI:7889; CHEMBL4303209; Paeoniflorin, analytical standard; Paeoniflorin, >=98% (HPLC); HMS3884D17; EBD18862; HY-N0293; ZINC8234328; CP0062; s2410; 3-HYDROXY-3-METHYLHEXANOICACID; AKOS025311455; CCG-269549; 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; AB0011492; C09959; AB01566855_01; 180P576; Q-100296; Q7124104; .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; [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; 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))-
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Species Origin Paeonia lactiflora ...     Click to Show/Hide
Paeonia lactiflora
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Saxifragales
Family: Paeoniaceae
Genus: Paeonia
Species: Paeonia lactiflora
Disease Parkinson's disease [ICD-11: 8A00] Investigative [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.291
 
MDCK Permeability
 -5.363
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.649
 
PPB
 54.9%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 3.119
 
T1/2
 2.749
Toxicity
DILI
 +
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 ++
 
Respiratory
 - - -
 
Human Hepatotoxicity
 - - -
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 - - -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 ++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C23H28O11
PubChem CID
442534
Canonical SMILES
CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)CO)O)O)O)O
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
InChIKey
YKRGDOXKVOZESV-WRJNSLSBSA-N
CAS Number
CAS 23180-57-6
ChEBI ID
CHEBI:7889
Herb ID
HBIN038606
SymMap ID
SMIT00129
TCMSP ID
MOL001924
TTD Drug ID
D0PD0F
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          X-ray irradiation      Scaphoid Fracture     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression CASP3  Molecule Info 
Pathway MAP
                    In-vitro Model Human skin fibroblasts Healthy Homo sapiens
                    Experimental
                    Result(s)		 Acteoside could protect the cells from X ray induced damage through enhancing the scavenging activity of ROS, decreasing the Bax/Bcl 2 ratio and downregulating the activity of procaspase 3, as well as modulating the mitogen activated protein kinase signaling pathways.
          Albiflorin      Chronic obstructive pulmonary disease     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Mice were exposed to X-ray radiation (400 Roentgen), and both mice and rabbits were intraperitoneally injected with cyclophosphamide (100.0 mg/kg) and cytarabine chloride (92.7 mg/kg), respectively, for 3 days to induce myelosuppression.
                    Experimental
                    Result(s)		 These results substantiate the marked therapeutic effects of CPA to ameliorate myelosuppression induced by radio and chemotherapy.
Target and Pathway
Target(s) .  Molecule Info 
Adenosine A1 receptor (ADORA1)  Molecule Info  [1]
Mothers against decapentaplegic 2 (SMAD2)  Molecule Info 
Mothers against decapentaplegic 7 (SMAD7)  Molecule Info 
KEGG Pathway cGMP-PKG signaling pathway Click to Show/Hide
2 cAMP signaling pathway
3 Sphingolipid signaling pathway
4 Neuroactive ligand-receptor interaction
5 Morphine addiction
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
2 RANKL Signaling Pathway
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
Reactome Adenosine P1 receptors Click to Show/Hide
2 G alpha (i) signalling events
WikiPathways Nucleotide GPCRs Click to Show/Hide
2 GPCRs, Class A Rhodopsin-like
3 GPCR ligand binding
4 GPCR downstream signaling
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 18).
Reference 2 Protective effects of acteoside against X?ray?induced damage in human skin fibroblasts. Mol Med Rep. 2015 Aug;12(2):2301-6.
Reference 3 Therapeutic effects of combination of paeoniflorin and albiflorin from Paeonia radix on radiation and chemotherapy-induced myelosuppression in mice and rabbits. Asian Pac J Cancer Prev. 2011;12(8):2031-7.
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