Natural Product (NP) Details

General Information of the NP (ID: NP0445)
Name
Cardamonin
Synonyms
CARDAMOMIN; Alpinetin chalcone; Dihydroxymethoxychalcone; 18956-16-6; 2',4'-dihydroxy-6'-methoxychalcone; UNII-H8KP1OJ8JX; 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one; 2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenyl-, (2E)-; H8KP1OJ8JX; (E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one; CHEMBL378104; 2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenyl-; (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one; (E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one; (E)-1-(2,4-Dihydroxy-6-methoxy-phenyl)-3-phenyl-propenone; Cardamoni; Cardamonin ,(S); 2'4'-Dihydroxy-6'-methoxy-chalcone; MLS000876992; SCHEMBL449220; MEGxp0_000534; Cardamonin, >=98% (HPLC); ACon1_000221; CHEBI:125601; HMS2271N04; HY-N0279; ZINC4716487; BDBM50185446; LMPK12120245; MFCD00238554; s3867; AKOS015896716; CCG-208127; DB14122; MCULE-6098713539; NCGC00180767-01; DS-15713; SMR000440601; B7085; CS-0008777; W1234; 309C149; A813330; J-012229; Q-100234; Q5038242; BRD-K61559475-001-01-0; 1-(2\\',4\\'-Dihydroxy-6\\'-methoxy-phenyl)-3-phenyl-propenone; (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one; (E)-1-(2,4-dihydroxy-6-methoxy-phenyl)-3-phenyl-prop-2-en-1-one; (E)-1-[2-methoxy-4,6-bis(oxidanyl)phenyl]-3-phenyl-prop-2-en-1-one; NCGC00180767-02!(E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
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Species Origin Alpinia zerumbet ...     Click to Show/Hide
Alpinia zerumbet
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Zingiberales
Family: Zingiberaceae
Genus: Alpinia
Species: Alpinia zerumbet
Disease Breast cancer [ICD-11: 2C60] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.914
 
MDCK Permeability
 -4.82
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 -0.055
 
PPB
 98.4%
 
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
 8.683
 
T1/2
 0.725
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
C16H14O4
PubChem CID
641785
Canonical SMILES
COC1=CC(=CC(=C1C(=O)C=CC2=CC=CC=C2)O)O
InChI
1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+
InChIKey
NYSZJNUIVUBQMM-BQYQJAHWSA-N
CAS Number
CAS 19309-14-9
Herb ID
HBIN019723
ETMC ID
1085
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     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 BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression BIRC5  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation mTOR  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation S6K1  Molecule Info 
Pathway MAP
Down-regulation Expression XIAP  Molecule Info 
Pathway MAP
                    In-vitro Model SK-OV-3 CVCL_0532 Ovarian serous cystadenocarcinoma Homo sapiens
A2780 CVCL_0134 Ovarian endometrioid adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Cardamonin enhances the anti-proliferative effect of cisplatin on ovarian cancer by suppressing the expression of anti-apoptotic proteins and activation of mTOR.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     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
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Down-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
Down-regulation Expression TCF7L2  Molecule Info 
Pathway MAP
                    In-vitro Model BGC-823 CVCL_3360 Gastric cancer Homo sapiens
                    In-vivo Model BGC-823/5-FU cells (5*106) were injected subcutaneously into the left flank of six-week-old BALB/c nude mice.
                    Experimental
                    Result(s)		 Cardamonin reduces 5-fluorouracil resistance of gastric cancer cells through targeting Wnt/beta-catenin signal pathway.
          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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ALDH1A1  Molecule Info 
Pathway MAP
Down-regulation Expression CCL2  Molecule Info 
Pathway MAP
Down-regulation Expression EZH2  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression MYC  Molecule Info 
Pathway MAP
Down-regulation Expression NANOG  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Down-regulation Expression PDK1  Molecule Info 
Pathway MAP
Down-regulation Expression POU5F1  Molecule Info 
Pathway MAP
Down-regulation Expression SETDB1  Molecule Info 
Pathway MAP
Down-regulation Expression SMYD3  Molecule Info 
Pathway MAP
Down-regulation Expression SOX2  Molecule Info 
Pathway MAP
Down-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model SUM190PT CVCL_3423 Breast inflammatory carcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
CAMA-1 CVCL_1115 Breast adenocarcinoma Homo sapiens
                    In-vivo Model To establish breast cancer xenografts in nude mice, SUM190 cells were mixed with Matrigel and injected under aseptic conditions into mammary fat pads of nude mice (n = 4-8 for each group, 2 * 106 cells per fat pad).
                    Experimental
                    Result(s)		 Cardamonin reduces chemotherapy-enriched breast cancer stem-like cells in vitro and in vivo.
Target and Pathway
Target(s) Beta-catenin (CTNNB1)  Molecule Info  [5]
Caterpiller protein 1.1 (NLRP3)  Molecule Info  [6]
DNA-binding factor KBF1 (p105)  Molecule Info  [5]
Hypoxia-inducible factor 1 alpha (HIF-1A)  Molecule Info  [1]
Interleukin-1 beta (IL1B)  Molecule Info  [6]
Toll-like receptor 3 (TLR3)  Molecule Info  [5]
KEGG Pathway HIF-1 signaling pathway Click to Show/Hide
2 mTOR signaling pathway
3 Thyroid hormone signaling pathway
4 Pathways in cancer
5 Proteoglycans in cancer
6 Renal cell carcinoma
7 Central carbon metabolism in cancer
8 Choline metabolism in cancer
9 Toll-like receptor signaling pathway
10 Hepatitis C
11 Hepatitis B
12 Influenza A
13 Herpes simplex infection
14 MAPK signaling pathway
15 Cytokine-cytokine receptor interaction
16 NF-kappa B signaling pathway
17 Apoptosis
18 Osteoclast differentiation
19 NOD-like receptor signaling pathway
20 Cytosolic DNA-sensing pathway
21 Hematopoietic cell lineage
22 TNF signaling pathway
23 Inflammatory mediator regulation of TRP channels
24 Non-alcoholic fatty liver disease (NAFLD)
25 Type I diabetes mellitus
26 Alzheimer's disease
27 Prion diseases
28 Salmonella infection
29 Pertussis
30 Legionellosis
31 Leishmaniasis
32 Chagas disease (American trypanosomiasis)
33 African trypanosomiasis
34 Malaria
35 Amoebiasis
36 Tuberculosis
37 Measles
38 Inflammatory bowel disease (IBD)
39 Rheumatoid arthritis
40 Graft-versus-host disease
41 Rap1 signaling pathway
42 Wnt signaling pathway
43 Hippo signaling pathway
44 Focal adhesion
45 Adherens junction
46 Tight junction
47 Signaling pathways regulating pluripotency of stem cells
48 Leukocyte transendothelial migration
49 Melanogenesis
50 Bacterial invasion of epithelial cells
51 Pathogenic Escherichia coli infection
52 HTLV-I infection
53 Colorectal cancer
54 Endometrial cancer
55 Prostate cancer
56 Thyroid cancer
57 Basal cell carcinoma
58 Arrhythmogenic right ventricular cardiomyopathy (ARVC)
59 Ras signaling pathway
60 cAMP signaling pathway
61 Chemokine signaling pathway
62 Sphingolipid signaling pathway
63 PI3K-Akt signaling pathway
64 RIG-I-like receptor signaling pathway
65 T cell receptor signaling pathway
66 B cell receptor signaling pathway
67 Neurotrophin signaling pathway
68 Prolactin signaling pathway
69 Adipocytokine signaling pathway
70 Cocaine addiction
71 Epithelial cell signaling in Helicobacter pylori infection
72 Shigellosis
73 Toxoplasmosis
74 Epstein-Barr virus infection
75 Transcriptional misregulation in cancer
76 Viral carcinogenesis
77 MicroRNAs in cancer
78 Pancreatic cancer
79 Chronic myeloid leukemia
80 Acute myeloid leukemia
81 Small cell lung cancer
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
2 Notch Signaling Pathway
3 TCR Signaling Pathway
4 Leptin Signaling Pathway
5 IL1 Signaling Pathway
6 IL2 Signaling Pathway
7 IL3 Signaling Pathway
8 TGF_beta_Receptor Signaling Pathway
9 Wnt Signaling Pathway
10 TNFalpha Signaling Pathway
Panther Pathway Angiogenesis Click to Show/Hide
2 Hypoxia response via HIF activation
3 VEGF signaling pathway
4 Toll receptor signaling pathway
5 Alzheimer disease-presenilin pathway
6 Cadherin signaling pathway
7 Wnt signaling pathway
8 p53 pathway feedback loops 2
9 CCKR signaling map ST
10 Apoptosis signaling pathway
11 T cell activation
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
2 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
Pathway Interaction Database AP-1 transcription factor network Click to Show/Hide
2 Hypoxic and oxygen homeostasis regulation of HIF-1-alpha
3 VEGFR1 specific signals
4 HIF-1-alpha transcription factor network
5 Notch-mediated HES/HEY network
6 Endogenous TLR signaling
7 IL27-mediated signaling events
8 IL12-mediated signaling events
9 IL1-mediated signaling events
10 IFN-gamma pathway
11 IL23-mediated signaling events
12 Cellular roles of Anthrax toxin
13 Degradation of beta catenin
14 Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met)
15 Coregulation of Androgen receptor activity
16 Arf6 trafficking events
17 Presenilin action in Notch and Wnt signaling
18 Integrin-linked kinase signaling
19 Nectin adhesion pathway
20 CDC42 signaling events
21 Canonical Wnt signaling pathway
22 FoxO family signaling
23 E-cadherin signaling events
24 Posttranslational regulation of adherens junction stability and dissassembly
25 E-cadherin signaling in the nascent adherens junction
26 E-cadherin signaling in keratinocytes
27 Regulation of nuclear beta catenin signaling and target gene transcription
28 Stabilization and expansion of the E-cadherin adherens junction
29 Signaling events mediated by VEGFR1 and VEGFR2
30 N-cadherin signaling events
31 RAC1 signaling pathway
32 TGF-beta receptor signaling
33 Fc-epsilon receptor I signaling in mast cells
34 BCR signaling pathway
35 LPA receptor mediated events
36 Atypical NF-kappaB pathway
37 Canonical NF-kappaB pathway
38 CD40/CD40L signaling
39 Alternative NF-kappaB pathway
40 Osteopontin-mediated events
41 Angiopoietin receptor Tie2-mediated signaling
42 Signaling events mediated by HDAC Class I
43 Regulation of Telomerase
44 Glucocorticoid receptor regulatory network
45 TNF receptor signaling pathway
46 IL2 signaling events mediated by PI3K
47 Ceramide signaling pathway
48 amb2 Integrin signaling
49 HIV-1 Nef: Negative effector of Fas and TNF-alpha
50 EPO signaling pathway
Reactome Regulation of gene expression by Hypoxia-inducible Factor Click to Show/Hide
2 Oxygen-dependent proline hydroxylation of Hypoxia-inducible Factor Alpha
3 BMAL1:CLOCK,NPAS2 activates circadian gene expression
4 NOTCH1 Intracellular Domain Regulates Transcription
5 Circadian Clock
6 Ligand-dependent caspase activation
7 MyD88-independent TLR3/TLR4 cascade
8 Trafficking and processing of endosomal TLR
9 RIP-mediated NFkB activation via ZBP1
10 TRIF-mediated programmed cell death
11 Activation of IRF3/IRF7 mediated by TBK1/IKK epsilon
12 IKK complex recruitment mediated by RIP1
13 TRAF6 mediated induction of TAK1 complex
14 Interleukin-1 signaling
15 Interleukin-1 processing
16 CLEC7A/inflammasome pathway
17 TCF dependent signaling in response to WNT
18 Formation of the beta-catenin:TCF transactivating complex
19 LRR FLII-interacting protein 1 (LRRFIP1) activates type I IFN production
20 CDO in myogenesis
21 Deactivation of the beta-catenin transactivating complex
22 Ca2+ pathway
23 Binding of TCF/LEF:CTNNB1 to target gene promoters
24 Disassembly of the destruction complex and recruitment of AXIN to the membrane
25 S33 mutants of beta-catenin aren't phosphorylated
26 S37 mutants of beta-catenin aren't phosphorylated
27 S45 mutants of beta-catenin aren't phosphorylated
28 T41 mutants of beta-catenin aren't phosphorylated
29 RHO GTPases activate IQGAPs
30 Activation of NF-kappaB in B cells
31 Regulated proteolysis of p75NTR
32 NF-kB is activated and signals survival
33 Senescence-Associated Secretory Phenotype (SASP)
34 FCERI mediated NF-kB activation
35 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
36 Transcriptional regulation of white adipocyte differentiation
37 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
38 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
39 IkBA variant leads to EDA-ID
40 CLEC7A (Dectin-1) signaling
41 CD209 (DC-SIGN) signaling
42 MAP3K8 (TPL2)-dependent MAPK1/3 activation
43 TRAF6 mediated NF-kB activation
WikiPathways SIDS Susceptibility Pathways Click to Show/Hide
2 Notch Signaling Pathway
3 Regulation of Hypoxia-inducible Factor (HIF) by Oxygen
4 Signaling by NOTCH1
5 Oncostatin M Signaling Pathway
6 Adipogenesis
7 AGE/RAGE pathway
8 Circadian Clock
9 Angiogenesis
10 Toll-like receptor signaling pathway
11 Cytosolic sensors of pathogen-associated DNA
12 Toll-Like Receptors Cascades
13 MyD88-independent cascade
14 Trafficking and processing of endosomal TLR
15 Regulation of toll-like receptor signaling pathway
16 Monoamine Transport
17 TCR Signaling Pathway
18 Type II interferon signaling (IFNG)
19 Senescence and Autophagy in Cancer
20 Cytokines and Inflammatory Response
21 MAPK Signaling Pathway
22 Myometrial Relaxation and Contraction Pathways
23 Aryl Hydrocarbon Receptor Pathway
24 IL1 and megakaryotyces in obesity
25 Hematopoietic Stem Cell Differentiation
26 Spinal Cord Injury
27 Allograft Rejection
28 Alzheimers Disease
29 Leptin signaling pathway
30 IL-1 signaling pathway
31 Interleukin-1 signaling
32 Folate Metabolism
33 Vitamin B12 Metabolism
34 Selenium Micronutrient Network
35 Serotonin Transporter Activity
36 NOD pathway
37 DNA Damage Response (only ATM dependent)
38 TGF Beta Signaling Pathway
39 Wnt Signaling Pathway
40 Wnt Signaling Pathway and Pluripotency
41 Wnt Signaling Pathway Netpath
42 Focal Adhesion
43 Extracellular vesicle-mediated signaling in recipient cells
44 Ectoderm Differentiation
45 Endoderm Differentiation
46 Hair Follicle Development: Cytodifferentiation (Part 3 of 3)
47 Hair Follicle Development: Organogenesis (Part 2 of 3)
48 Hair Follicle Development: Induction (Part 1 of 3)
49 Primary Focal Segmental Glomerulosclerosis FSGS
50 BDNF signaling pathway
51 Integrated Pancreatic Cancer Pathway
52 Gastric cancer network 2
53 Corticotropin-releasing hormone
54 Pathogenic Escherichia coli infection
55 Arrhythmogenic Right Ventricular Cardiomyopathy
56 Neural Crest Differentiation
57 TWEAK Signaling Pathway
58 miR-targeted genes in muscle cell - TarBase
59 miR-targeted genes in lymphocytes - TarBase
60 miR-targeted genes in leukocytes - TarBase
61 Integrated Breast Cancer Pathway
62 Myogenesis
63 Heart Development
64 MicroRNAs in cardiomyocyte hypertrophy
65 Androgen receptor signaling pathway
66 Oxidative Stress
67 IL-4 Signaling Pathway
68 Apoptosis Modulation by HSP70
69 Apoptosis-related network due to altered Notch3 in ovarian cancer
70 Selenium Metabolism and Selenoproteins
71 Cardiac Hypertrophic Response
72 Fc epsilon receptor (FCERI) signaling
73 Transcriptional Regulation of White Adipocyte Differentiation
74 Signaling by the B Cell Receptor (BCR)
75 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
76 Structural Pathway of Interleukin 1 (IL-1)
77 EBV LMP1 signaling
78 Aryl Hydrocarbon Receptor
79 T-Cell Receptor and Co-stimulatory Signaling
80 Apoptosis
81 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
82 TNF alpha Signaling Pathway
83 B Cell Receptor Signaling Pathway
84 TSLP Signaling Pathway
85 IL17 signaling pathway
86 RANKL/RANK Signaling Pathway
87 Signalling by NGF
88 TCR signaling
89 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
90 Interleukin-1 processing
91 Apoptosis Modulation and Signaling
92 TFs Regulate miRNAs related to cardiac hypertrophy
93 Osteopontin Signaling
References
Reference 1 Cardamonin inhibits breast cancer growth by repressing HIF-1Alpha-dependent metabolic reprogramming. J Exp Clin Cancer Res. 2019 Aug 27;38(1):377.
Reference 2 Cardamonin enhances the anti-proliferative effect of cisplatin on ovarian cancer. Oncol Lett. 2018 Mar;15(3):3991-3997.
Reference 3 Cardamonin, a natural chalcone, reduces 5-fluorouracil resistance of gastric cancer cells through targeting Wnt/beta-catenin signal pathway. Invest New Drugs. 2020 Apr;38(2):329-339.
Reference 4 Cardamonin reduces chemotherapy-enriched breast cancer stem-like cells in vitro and in vivo. Oncotarget. 2016 Jan 5;7(1):771-85.
Reference 5 Beta-Catenin and NF-KappaB co-activation triggered by TLR3 stimulation facilitates stem cell-like phenotypes in breast cancer. Cell Death Differ. 2015 Feb;22(2):298-310.
Reference 6 Cardamonin from a medicinal herb protects against LPS-induced septic shock by suppressing NLRP3 inflammasome. Acta Pharm Sin B. 2019 Jul;9(4):734-744.
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