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Paeoniflorin
- Family: Plantae - Lactobacillaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@]23C[C@@H]4[C@@]3(COC(=O)c3ccccc3)[C@@H]3O[C@@]2(C)C[C@]4(O3)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| 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 |
| InChIKey | YKRGDOXKVOZESV-WRJNSLSBSA-N |
| Formula | C23H28O11 |
| HBA | 11 |
| HBD | 5 |
| MW | 480.47 |
| Rotatable Bonds | 6 |
| TPSA | 164.37 |
| LogP | -1.36 |
| Number Rings | 8 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 480.16 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Lactobacillus brevis | Lactobacillaceae | Plantae | 1580 |
Showing of synonyms
Paeoniflorin
Peoniflorin
Paeonia moutan
NSC 178886
UNII-21AIQ4EV64
21AIQ4EV64
CCRIS 6494
EINECS 245-476-2
PAEONIFLORIN (USP-RS)
PAEONIFLORIN [USP-RS]
NSC-178886
245-476-2
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
23180-57-6
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%)
[(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
MFCD00869331
((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
NSC178886
.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
Paeoniflorin (Standard)
SCHEMBL549033
CHEBI:7889
CHEMBL4303209
DTXSID2042648
HY-N0293R
Paeoniflorin, analytical standard
Paeoniflorin, >=98% (HPLC)
YKRGDOXKVOZESV-WRJNSLSBSA-N
GLXC-13167
HMS3884D17
HY-N0293
MSK157242
S2410
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
1ST157242
NS00027374
C09959
AB01566855_01
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.))-
[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))-
Pubchem:
442534
Cas:
23180-57-6
Gnps:
CCMSLIB00005749140
Zinc:
ZINC000008234328
Kegg Ligand:
C09959
Chebi:
7889
Nmrshiftdb2:
60026388
Chembl:
CHEMBL4303209
Drugbank:
DB16288
Selleck:
paeoniflorin
CPRiL:
55113
SMILES: c1ccccc1C(=O)OCC23C4(C5CC(C2C4)OC3O5)OC6CCCCO6
Level: 2
Mol. Weight: 480.47 g/mol
SMILES: c1ccccc1C(=O)OCC23C4C5CC(C2C4)OC3O5
Level: 1
Mol. Weight: 480.47 g/mol
SMILES: O1CCCCC1OC23C4C(C2)C5CC3OC4O5
Level: 1
Mol. Weight: 480.47 g/mol
SMILES: C12C3C4CC(C1C3)OC2O4
Level: 0
Mol. Weight: 480.47 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 480.47 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 480.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.06
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.640
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.69
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.700
- Plasma Protein Binding
- 79.64
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 0.320
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.310
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.050
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.520
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -263.160
- Rat (Acute)
- 3.570
- Rat (Chronic Oral)
- 3.630
- Fathead Minnow
- 3.920
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 484.670
- Hydration Free Energy
- -3.320
- Log(D) at pH=7.4
- 0.930
- Log(P)
- -0.4
- Log S
- -2.47
- Log(Vapor Pressure)
- -12.89
- Melting Point
- 151.09
- pKa Acid
- 4.96
- pKa Basic
- 3.02
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8677 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8594 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7876 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7634 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7387 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7260 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7212 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7180 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7083 |
| Carbonic anhydrase | Q39588 | Q39588_CHLRE | Chlamydomonas reinhardtii | 2 | 0.7019 |