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Natural Product (NP) Details

General Information of the NP (ID: NP9550)
Name
Garcinol
Synonyms
Camboginol; 78824-30-3; AC1Q1NUM; GTPL7001; QDKLRKZQSOQWJQ-SMDXAGPFSA-N; ZINC4098424; AKOS025142024; (1S,5R,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-1-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-5,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione; (1R,5R,7R)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-Bicyclo[3.3.1]non-3-ene-2,9-dione
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Species Origin Cicer arietinum ...     Click to Show/Hide
Cicer arietinum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Cicer
Species: Cicer arietinum
Garcinia dulcis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malpighiales
Family: Clusiaceae
Genus: Garcinia
Species: Garcinia dulcis
Garcinia indica
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malpighiales
Family: Clusiaceae
Genus: Garcinia
Species: Garcinia indica
Disease Stomach cancer [ICD-11: 2B72] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C38H50O6
PubChem CID
5281560
Canonical SMILES
CC(=CCC1CC2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC(CC=C(C)C)C(=C)C)C
InChI
1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-41H,7,13,15,18,20-21H2,1-6,8-10H3/b32-31-/t27-,28+,37+,38-/m0/s1
InChIKey
DTTONLKLWRTCAB-BZSUNBQASA-N
CAS Number
CAS 78824-30-3
Herb ID
HBIN027349
TTD Drug ID
D03JNC
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
                 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 Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation PIK3CB  Molecule Info 
Pathway MAP
                    In-vitro Model OVCAR-3 CVCL_0465 Ovarian serous adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)
Garcinol in combination with DDP promoted cell apoptosis in human ovarian cancer cells.
Target and Pathway
Target(s) Histone acetyltransferase KAT2B (KAT2B)  Molecule Info  [3]
Histone acetyltransferase KAT6B (KAT6B)  Molecule Info  [3]
KEGG Pathway cAMP signaling pathway Click to Show/Hide
2 HIF-1 signaling pathway
3 FoxO signaling pathway
4 Cell cycle
5 Wnt signaling pathway
6 Notch signaling pathway
7 TGF-beta signaling pathway
8 Adherens junction
9 Jak-STAT signaling pathway
10 Long-term potentiation
11 Melanogenesis
12 Thyroid hormone signaling pathway
13 Glucagon signaling pathway
14 Huntington's disease
15 Tuberculosis
16 Hepatitis B
17 Influenza A
18 HTLV-I infection
19 Herpes simplex infection
20 Epstein-Barr virus infection
21 Pathways in cancer
22 Viral carcinogenesis
23 MicroRNAs in cancer
24 Renal cell carcinoma
25 Prostate cancer
Panther Pathway p53 pathway Click to Show/Hide
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Signaling events mediated by HDAC Class III
3 E2F transcription factor network
4 Signaling events mediated by HDAC Class I
5 FoxO family signaling
6 Regulation of Androgen receptor activity
7 Retinoic acid receptors-mediated signaling
8 p53 pathway
Reactome Pre-NOTCH Transcription and Translation Click to Show/Hide
2 YAP1- and WWTR1 (TAZ)-stimulated gene expression
3 NOTCH1 Intracellular Domain Regulates Transcription
4 Constitutive Signaling by NOTCH1 PEST Domain Mutants
5 Constitutive Signaling by NOTCH1 HD+PEST Domain Mutants
6 HATs acetylate histones
7 Notch-HLH transcription pathway
8 RNA Polymerase I Transcription Initiation
9 Regulation of gene expression by Hypoxia-inducible Factor
10 RORA activates gene expression
11 BMAL1:CLOCK,NPAS2 activates circadian gene expression
12 Polo-like kinase mediated events
13 PPARA activates gene expression
14 Formation of the beta-catenin:TCF transactivating complex
15 NOTCH2 intracellular domain regulates transcription
16 DNA Damage/Telomere Stress Induced Senescence
17 LRR FLII-interacting protein 1 (LRRFIP1) activates type I IFN production
18 Attenuation phase
19 Transcriptional regulation of white adipocyte differentiation
20 Circadian Clock
21 HDR through Single Strand Annealing (SSA)
22 HDR through Homologous Recombination (HRR)
23 Recruitment and ATM-mediated phosphorylation of repair and signaling proteins at DNA double strand breaks
24 Nonhomologous End-Joining (NHEJ)
25 Processing of DNA double-strand break ends
26 Presynaptic phase of homologous DNA pairing and strand exchange
27 Formation of TC-NER Pre-Incision Complex
28 Dual incision in TC-NER
29 Gap-filling DNA repair synthesis and ligation in TC-NER
30 G2/M DNA damage checkpoint
31 TRAF3-dependent IRF activation pathway
32 TRAF6 mediated IRF7 activation
33 Factors involved in megakaryocyte development and platelet production
WikiPathways Nuclear Receptors Meta-Pathway Click to Show/Hide
2 YAP1- and WWTR1 (TAZ)-stimulated gene expression
3 Notch Signaling Pathway
4 RNA Polymerase I, RNA Polymerase III, and Mitochondrial Transcription
5 Androgen receptor signaling pathway
6 SIDS Susceptibility Pathways
7 Notch Signaling Pathway
8 TGF Beta Signaling Pathway
9 Wnt Signaling Pathway and Pluripotency
10 IL-4 Signaling Pathway
11 TGF beta Signaling Pathway
12 Kit receptor signaling pathway
13 Aryl Hydrocarbon Receptor Pathway
14 Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
15 Cytosolic sensors of pathogen-associated DNA
16 Pre-NOTCH Expression and Processing
17 Transcriptional Regulation of White Adipocyte Differentiation
18 Regulation of Hypoxia-inducible Factor (HIF) by Oxygen
19 Signaling by NOTCH1
20 Signaling by NOTCH2
21 Aryl Hydrocarbon Receptor
22 Integrated Pancreatic Cancer Pathway
23 Signaling Pathways in Glioblastoma
24 Integrated Breast Cancer Pathway
25 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
26 Factors involved in megakaryocyte development and platelet production
27 Circadian Clock
28 Cell Cycle
References
Reference 1 Garcinol acts as an antineoplastic agent in human gastric cancer by inhibiting the PI3K/AKT signaling pathway. Oncol Lett. 2020 Jul;20(1):667-676.
Reference 2 Garcinol Alone and in Combination With Cisplatin Affect Cellular Behavior and PI3K/AKT Protein Phosphorylation in Human Ovarian Cancer Cells. Dose Response. 2020 May 19;18(2):1559325820926732.
Reference 3 Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene e... J Biol Chem. 2004 Aug 6;279(32):33716-26.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China