Natural Product (NP) Details

General Information of the NP (ID: NP6815)
Name
Acacetin
Synonyms
acacetin; 480-44-4; Linarigenin; 5,7-Dihydroxy-4'-methoxyflavone; 4'-Methoxyapigenin; Buddleoflavonol; Acacetine; Linarisenin; 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one; Apigenin 4'-methyl ether; Akatsetin; 5,7-Dioxy-4'-methoxyflavone; Apisenin 4'-methyl ether; Apigenin 4'-dimethyl ether; 5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one; 4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-METHOXYPHENYL)-; UNII-KWI7J0A2CC; NSC 76061; Flavone, 5,7-dihydroxy-4'-methoxy-; ACAETIN; 5,7-Dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone; NSC76061; KWI7J0A2CC; 4'-Methoxy-5,7-dihydroxyflavone; MLS002693970; CHEMBL243664; CHEBI:15335; MFCD00016936; NSC-76061; SMR001233299; SR-01000841189; EINECS 207-552-3; BRN 0277879; Acaceztin; 4-Methylapigenin; 4'-Methylapigenin; Prestwick_49; 4'-O-Methylapigenin; 5,7-Dihydroxy-4; Kinome_3212; Spectrum_000135; Prestwick0_000695; Prestwick1_000695; Prestwick2_000695; Prestwick3_000695; Spectrum5_000930; Acacetin, analytical standard; BSPBio_000849; KBioSS_000595; SPECTRUM200499; 5-18-04-00575 (Beilstein Handbook Reference); MLS002153960; DivK1c_000878; SCHEMBL107712; SPBio_002770; BPBio1_000935; 00017_FLUKA; BCBcMAP01_000082; BDBM23415; HMS502L20; KBio1_000878; KBio2_000595; KBio2_003163; KBio2_005731; DTXSID00197383; Flavone,7-dihydroxy-4'-methoxy-; NINDS_000878; HMS1570K11; HMS1922P12; HMS2097K11; HMS2234J17; HMS3374F03; Acacetin, >=97.0% (HPLC); BCP15815; HY-N0451; ZINC3871358; LMPK12110468; s5318; AKOS015903365; CCG-208517; CS-5336; MCULE-8773156096; IDI1_000878; SMP1_000001; NCGC00016458-01; NCGC00016458-02; NCGC00016458-03; NCGC00016458-04; NCGC00016458-05; NCGC00095213-01; NCGC00095213-02; NCGC00095213-03; NCGC00179402-01; AK114502; AS-70345; CAS-480-44-4; ST066889; WLN: T66 BO EVJ CR DO1& GQ IQ; AB0021899; DB-051509; FT-0645060; N2109; W1621; Flavone, 5,7-dihydroxy-4'-methoxy- (8CI); A14741; C01470; 480A444; Q2822213; SR-01000841189-3; SR-01000841189-4; BRD-K77685744-001-03-6; BRD-K77685744-001-07-7; 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one #; 4H-1-Benzopyran-4-one,7-dihydroxy-2-(4-methoxyphenyl)-; BE7185D3-6331-4E84-8C8E-5D10E505E37A
    Click to Show/Hide
Species Origin Acacia farnesiana ...     Click to Show/Hide
Acacia farnesiana
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Vachellia
Species: Acacia farnesiana
Disease Ischemic heart disease [ICD-11: BA6Z] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.911
 
MDCK Permeability
 -4.798
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 -0.242
 
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
 5.282
 
T1/2
 0.926
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.
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C16H12O5
PubChem CID
5280442
Canonical SMILES
COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
InChI
1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3
InChIKey
DANYIYRPLHHOCZ-UHFFFAOYSA-N
CAS Number
CAS 480-44-4
ChEBI ID
CHEBI:15335
Herb ID
HBIN014294
SymMap ID
SMIT00117
TCMSP ID
MOL001689
TTD Drug ID
D0NS1S
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Doxorubicin      Solid tumour/cancer     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
                    Biological
                    Regulation		 Down-regulation MDR1 transporter
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H1299 CVCL_0060 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Their combination leads to more retention of doxorubicin in the cells by modulating drug trasporter and thus enhances its therapeutic potential.
          Pinostrobin      Parkinson's disease     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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
T-47D CVCL_0553 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Acacetin and Pinostrobin inhibit malignant breast epithelial cell adhesion and focal adhesion formation to attenuate cell migration.
Target and Pathway
Target(s) Arachidonate 5-lipoxygenase (5-LOX)  Molecule Info  [4]
Cytochrome P450 1B1 (CYP1B1)  Molecule Info  [5]
Xanthine dehydrogenase/oxidase (XDH)  Molecule Info  [6]
BioCyc Superpathway of tryptophan utilization Click to Show/Hide
2 Superpathway of melatonin degradation
3 Melatonin degradation I
4 Purine nucleotides degradation
5 Urate biosynthesis/inosine 5'-phosphate degradation
6 Guanosine nucleotides degradation
7 Adenosine nucleotides degradation
8 Retinoate biosynthesis II
9 Aspirin-triggered lipoxin biosynthesis
10 Resolvin D biosynthesis
11 Leukotriene biosynthesis
12 Lipoxin biosynthesis
13 Aspirin triggered resolvin D biosynthesis
14 Aspirin triggered resolvin E biosynthesis
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
7 Purine metabolism
8 Caffeine metabolism
9 Drug metabolism - other enzymes
10 Metabolic pathways
11 Peroxisome
12 Arachidonic acid metabolism
13 Serotonergic synapse
14 Toxoplasmosis
NetPath Pathway TSH Signaling Pathway Click to Show/Hide
2 IL4 Signaling Pathway
3 TGF_beta_Receptor Signaling Pathway
Panther Pathway Adenine and hypoxanthine salvage pathway Click to Show/Hide
2 Purine metabolism
Pathwhiz Pathway Caffeine Metabolism Click to Show/Hide
2 Purine Metabolism
3 Arachidonic Acid Metabolism
Reactome Endogenous sterols Click to Show/Hide
2 Purine catabolism
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
16 Oxidative Stress
17 Effects of Nitric Oxide
18 Metabolism of nucleotides
19 Selenium Micronutrient Network
20 Vitamin D Receptor Pathway
21 Arachidonic acid metabolism
22 Eicosanoid Synthesis
References
Reference 1 Acacetin Protects Myocardial Cells against Hypoxia-Reoxygenation Injury through Activation of Autophagy. J Immunol Res. 2021 Jun 29;2021:9979843.
Reference 2 Acacetin enhances the therapeutic efficacy of doxorubicin in non-small-cell lung carcinoma cells. PLoS One. 2017 Aug 31;12(8):e0182870.
Reference 3 Acacetin and Pinostrobin Inhibit Malignant Breast Epithelial Cell Adhesion and Focal Adhesion Formation to Attenuate Cell Migration. Integr Cancer Ther. Jan-Dec 2020;19:1534735420918945.
Reference 4 Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation. J Nat Prod. 1999 Sep;62(9):1241-5.
Reference 5 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
Reference 6 Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link