Natural Product (NP) Details

General Information of the NP (ID: NP1047)
Name
Zerumbone
Synonyms
Zerumbone; 471-05-6; (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one; (E,E,E)-2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-one; CHEMBL245412; 2E,6E,9E-humulatrien-8-one; CHEBI:63892; C15H22O; Zerumbone (6CI,7CI); 2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one; SCHEMBL12831266; Zerumbone, >=98% (HPLC); HY-N7015; BDBM50241296; MFCD03700769; NSC698299; s5928; ZINC28878195; CCG-208558; NSC-698299; CS-0003365; C20262; Q27132897
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Species Origin Zingiber zerumbet ...     Click to Show/Hide
Zingiber zerumbet
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Zingiberales
Family: Zingiberaceae
Genus: Zingiber
Species: Zingiber zerumbet
Disease Breast cancer [ICD-11: 2C60] Investigative [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.643
 
MDCK Permeability
 -4.661
 
PAMPA
 - - -
 
HIA
 - -
 
Distribution
VDss
 0.182
 
PPB
 67.5%
 
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
 9.316
 
T1/2
 0.527
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
C15H22O
PubChem CID
5470187
Canonical SMILES
CC1=CCC(C=CC(=O)C(=CCC1)C)(C)C
InChI
1S/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8+,13-7+
InChIKey
GIHNTRQPEMKFKO-SKTNYSRSSA-N
CAS Number
CAS 471-05-6
ChEBI ID
CHEBI:63892
Herb ID
HBIN048883
SymMap ID
SMIT06255
TCMSP ID
MOL004314
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Nimesulide      Colorectal 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
                    Molecule(s)
                    Regulation		 Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
                    In-vivo Model Colitis was induced in female ICR mice at 7 weeks of age.
                    Experimental
                    Result(s)		 ZER is a novel food factor for mitigating experimental UC and that use of a combination of agents, with different modes of actions, may be an effective anti-inflammatory strategy.
          Cisplatin      Bladder 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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model HeLa CVCL_0030 Endocervical adenocarcinoma Homo sapiens
                    In-vivo Model Inbred BALB/c mice with CIN were injected peritoneally with isotonic sodium chloride solution (positive control), CIS, ZER, and a combination of both compounds.
                    Experimental
                    Result(s)		 The combination of ZER and CIS has modulated the serum level of interleukin 6 when compared with that in mice treated with isotonic sodium chloride solution.
Target and Pathway
Target(s) Baculoviral IAP repeat-containing 1 (AKT1S1)  Molecule Info  [4]
Caspase-3 (CASP3)  Molecule Info  [4]
Forkhead box protein O1A (FOXO1)  Molecule Info  [4]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 p53 signaling pathway
3 Apoptosis
4 Natural killer cell mediated cytotoxicity
5 TNF signaling pathway
6 Serotonergic synapse
7 Non-alcoholic fatty liver disease (NAFLD)
8 Alzheimer's disease
9 Parkinson's disease
10 Amyotrophic lateral sclerosis (ALS)
11 Huntington's disease
12 Epithelial cell signaling in Helicobacter pylori infection
13 Pertussis
14 Legionellosis
15 Toxoplasmosis
16 Amoebiasis
17 Tuberculosis
18 Hepatitis B
19 Herpes simplex infection
20 Pathways in cancer
21 Viral carcinogenesis
22 Proteoglycans in cancer
23 MicroRNAs in cancer
24 Colorectal cancer
25 Viral myocarditis
26 FoxO signaling pathway
27 AMPK signaling pathway
28 Insulin signaling pathway
29 Thyroid hormone signaling pathway
30 Glucagon signaling pathway
31 Transcriptional misregulation in cancer
32 Prostate cancer
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
2 IL2 Signaling Pathway
3 IL4 Signaling Pathway
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 FAS signaling pathway
3 Huntington disease
4 CCKR signaling map ST
5 Insulin/IGF pathway-protein kinase B signaling cascade
6 PI3 kinase pathway
Pathway Interaction Database LPA receptor mediated events Click to Show/Hide
2 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
3 FAS (CD95) signaling pathway
4 Role of Calcineurin-dependent NFAT signaling in lymphocytes
5 Posttranslational regulation of adherens junction stability and dissassembly
6 p75(NTR)-mediated signaling
7 HIV-1 Nef: Negative effector of Fas and TNF-alpha
8 Caspase Cascade in Apoptosis
9 Syndecan-2-mediated signaling events
10 Regulation of nuclear SMAD2/3 signaling
11 Signaling events mediated by HDAC Class III
12 Angiopoietin receptor Tie2-mediated signaling
13 CXCR4-mediated signaling events
14 FoxO family signaling
15 Regulation of Androgen receptor activity
16 IL6-mediated signaling events
17 Class I PI3K signaling events mediated by Akt
Reactome SMAC binds to IAPs Click to Show/Hide
2 SMAC-mediated dissociation of IAP:caspase complexes
3 Apoptotic cleavage of cellular proteins
4 Degradation of the extracellular matrix
5 NADE modulates death signalling
6 Activation of DNA fragmentation factor
7 Caspase-mediated cleavage of cytoskeletal proteins
8 AKT phosphorylates targets in the nucleus
9 Regulation of gene expression in beta cells
10 AKT-mediated inactivation of FOXO1A
11 Constitutive Signaling by AKT1 E17K in Cancer
12 MAPK6/MAPK4 signaling
WikiPathways DNA Damage Response Click to Show/Hide
2 SIDS Susceptibility Pathways
3 Apoptosis Modulation by HSP70
4 MAPK Signaling Pathway
5 Copper homeostasis
6 FAS pathway and Stress induction of HSP regulation
7 Signaling by Hippo
8 Apoptosis
9 Amyotrophic lateral sclerosis (ALS)
10 Spinal Cord Injury
11 BDNF signaling pathway
12 Integrated Pancreatic Cancer Pathway
13 Oncostatin M Signaling Pathway
14 Parkinsons Disease Pathway
15 Corticotropin-releasing hormone
16 Allograft Rejection
17 AGE/RAGE pathway
18 TNF alpha Signaling Pathway
19 Prostate Cancer
20 Alzheimers Disease
21 TWEAK Signaling Pathway
22 Integrated Breast Cancer Pathway
23 Signalling by NGF
24 Integrated Cancer pathway
25 Regulation of Apoptosis
26 Intrinsic Pathway for Apoptosis
27 Apoptotic execution phase
28 Apoptosis Modulation and Signaling
29 miRNA Regulation of DNA Damage Response
30 ErbB Signaling Pathway
31 Insulin Signaling
32 EGF/EGFR Signaling Pathway
33 Pregnane X Receptor pathway
34 Endoderm Differentiation
35 Adipogenesis
36 B Cell Receptor Signaling Pathway
37 Signaling Pathways in Glioblastoma
38 FSH signaling pathway
39 Leptin signaling pathway
40 Regulation of beta-cell development
41 Androgen receptor signaling pathway
References
Reference 1 Zerumbone modulates CD1d expression and lipid antigen presentation pathway in breast cancer cells. Toxicol In Vitro. 2017 Oct;44:74-84.
Reference 2 Suppression of dextran sodium sulfate-induced colitis in mice by zerumbone, a subtropical ginger sesquiterpene, and nimesulide: separately and in combination. Biochem Pharmacol. 2003 Oct 1;66(7):1253-61.
Reference 3 Combination of zerumbone and cisplatin to treat cervical intraepithelial neoplasia in female BALB/c mice. Int J Gynecol Cancer. 2009 Aug;19(6):1004-10.
Reference 4 Zerumbone suppresses IKKAlpha, Akt, and FOXO1 activation, resulting in apoptosis of GBM 8401 cells. J Biomed Sci. 2012 Oct 5;19(1):86.
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