Natural Product (NP) Details

General Information of the NP (ID: NP8937)
Name
Pinocembrin
Synonyms
Pinocembrin; 480-39-7; (+)-Pinocembrin; (2S)-pinocembrin; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2S)-; (S)-5,7-dihydroxy-2-phenylchroman-4-one; UNII-8T7C8CH791; (2s)-5,7-dihydroxy-2-phenyl-2,3-dihydro-4h-chromen-4-one; (S)-5,7-dihydroxyflavanone; CHEMBL399910; CHEBI:28157; (S)-2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one; 8T7C8CH791; Pinocembrin (6CI); (2S)-5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one; SMR000232372; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (-)-; NSC 43318; NSC 279005; NSC 661207; NSC43318; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (S)-; NSC-43318; NSC661207; NSC-279005; Spectrum_001879; SpecPlus_000896; Spectrum2_001670; Spectrum3_001635; Spectrum4_001765; Spectrum5_000349; Oprea1_508274; BSPBio_003329; KBioGR_002249; KBioSS_002406; MLS000697595; MLS000728654; DivK1c_006992; SPBio_001859; DTXSID3075412; SCHEMBL10026578; BDBM26667; KBio1_001936; KBio2_002401; KBio2_004969; KBio2_007537; KBio3_002549; ZINC73693; HMS2205J20; HY-N0575; CCG-39668; LMPK12140214; s3941; STL578139; AKOS004111068; SDCCGMLS-0066749.P001; NCGC00178137-01; AS-56293; ST023293; (2S)-5,7-dihydroxy-2-phenylchroman-4-one; CS-0009111; (2S)-5,7-dihydroxy-2-phenyl-chroman-4-one; C09827; SR-01000762561; SR-01000762561-3; BRD-K94689771-001-02-5; Pinocembrin, analytical standard, 95% (TLC), solid; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (S)-(-)-
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Species Origin Eucalyptus ...     Click to Show/Hide
Eucalyptus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Myrtales
Family: Myrtaceae
Genus: Eucalyptus
Disease Ischemic stroke [ICD-11: 8B11] Phase 2 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.966
 
MDCK Permeability
 -4.766
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 0.261
 
PPB
 97.6%
 
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
 6.213
 
T1/2
 1.047
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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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H12O4
PubChem CID
68071
Canonical SMILES
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
InChI
1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m0/s1
InChIKey
URFCJEUYXNAHFI-ZDUSSCGKSA-N
CAS Number
CAS 480-39-7
ChEBI ID
CHEBI:28157
Herb ID
HBIN039998
SymMap ID
SMIT02875
TCMSP ID
MOL000230
TTD Drug ID
D0G5CS
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Simvastatin      Hyper-lipoproteinaemia     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     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 VEGFA  Molecule Info 
Pathway MAP
                    In-vivo Model ApoE / mice (8 weeks old) were fed a high fat diet (21% fat and 0.15% cholesterol).
                    Experimental
                    Result(s)		 The combination of simvastatin and pinocembrin synergistically inhibited atherosclerotic lesion development in ApoE-/- mice with hyperlipidemia, which is partially dependent on the protective of vascular endothelium.
Target and Pathway
Target(s) Cytochrome P450 1B1 (CYP1B1)  Molecule Info  [3]
BioCyc Superpathway of tryptophan utilization Click to Show/Hide
2 Superpathway of melatonin degradation
3 Melatonin degradation I
KEGG Pathway Steroid hormone biosynthesis Click to Show/Hide
2 Tryptophan metabolism
3 Metabolism of xenobiotics by cytochrome P450
4 Ovarian steroidogenesis
5 Chemical carcinogenesis
6 MicroRNAs in cancer
NetPath Pathway TSH Signaling Pathway Click to Show/Hide
2 IL4 Signaling Pathway
3 TGF_beta_Receptor Signaling Pathway
Reactome Endogenous sterols Click to Show/Hide
WikiPathways Metapathway biotransformation Click to Show/Hide
2 Estrogen metabolism
3 Benzo(a)pyrene metabolism
4 Tamoxifen metabolism
5 Tryptophan metabolism
6 Oxidation by Cytochrome P450
7 Nuclear Receptors Meta-Pathway
8 Estrogen Receptor Pathway
9 Sulindac Metabolic Pathway
10 Arylhydrocarbon receptor (AhR) signaling pathway
11 miR-targeted genes in muscle cell - TarBase
12 miR-targeted genes in lymphocytes - TarBase
13 miR-targeted genes in epithelium - TarBase
14 miR-targeted genes in adipocytes - TarBase
15 Phase 1 - Functionalization of compounds
References
Reference 1 ClinicalTrials.gov (NCT02059785) Phase 2 Study of Pinocembrin Injection to Treat Ischemic Stroke
Reference 2 Inhibitory effect of the combination therapy of simvastatin and pinocembrin on atherosclerosis in ApoE-deficient mice. Lipids Health Dis. 2012 Dec 5;11:166.
Reference 3 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
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