Natural Product (NP) Details

General Information of the NP (ID: NP2010)
Name
Delphinidin
Synonyms
Delphinidin chloride; Delphinidin; 528-53-0; Delphinidine; Delphinidol; Ephdine; Delfinidol chloride; UNII-EM6MD4AEHE; 8012-95-1; 1-Benzopyrylium, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, chloride; EM6MD4AEHE; 2-(3,4,5-trihydroxyphenyl)chromenylium-3,5,7-triol chloride; 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)benzopyrylium chloride; IdB 1056; CHEBI:38701; 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium chloride; MFCD00016663; Paraffin, liquid, pure; 2-(3,4,5-trihydroxyphenyl)chromenylium-3,5,7-triol;chloride; 3,3',4',5,5',7-Hexahydroxyflavylium chloride; Delphinidine; Delphinidol; Ephdine; IdB 1056;Delfinidol chloride; Delphinidin; CHEMBL590878; Delphinidin chloride, analytical standard; 3,3',4',5,5',7-Hexahydroxy-2-phenylbenzopyrylium chloride; CCRIS 2518; EINECS 208-437-0; C15H11O7.Cl; 2-(3,4,5-trihydroxyphenyl)chromenylium-3,5,7-triol; Delphinidinchloride; 2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium-3,5,7-triol; Paraffin, liquid, technical; SCHEMBL22369; IdB-1056; DTXSID701019982; 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromenium chloride; BCP15819; 6267AF; AKOS027326494; FT-0645153; FT-0665679; A11978; Q367258; Flavylium 3,3',4',5,5',7-hexahydroxy-, chloride (8CI); UNII-R911H793SU component FFNDMZIBVDSQFI-UHFFFAOYSA-N; 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium chloride; 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-1lambda-chromen-1-ylium
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Species Origin Aristotelia chilensis ...     Click to Show/Hide
Aristotelia chilensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Oxalidales
Family: Elaeocarpaceae
Genus: Aristotelia
Species: Aristotelia chilensis
Disease Cardiovascular disease [ICD-11: BA00-BE2Z] Phase 2 [1]
Structure
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2D MOL

3D MOL

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Formula
C15H11ClO7
PubChem CID
68245
Canonical SMILES
C1=C(C=C(C(=C1O)O)O)C2=[O+]C3=CC(=CC(=C3C=C2O)O)O.[Cl-]
InChI
1S/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H
InChIKey
FFNDMZIBVDSQFI-UHFFFAOYSA-N
CAS Number
CAS 8012-95-1
ChEBI ID
CHEBI:38701
Herb ID
HBIN023132
SymMap ID
SMIT00215
TCMSP ID
MOL004798
TTD Drug ID
D0ZN1R
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          TNF-related apoptosis inducing ligand      Lung 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		 Up-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
DU145 CVCL_0105 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Delphinidin sensitizes prostate cancer cells to TRAIL-induced apoptosis, by inducing DR5 and causing caspase-mediated HDAC3 cleavage.
          Arsenite      Prostate 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
                    Molecule(s)
                    Regulation		 Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
                    Experimental
                    Result(s)		 Delphinidin-induced sensitization of HL-60 cells to As(III) may lead to dose reduction of As(III) in clinical application, and ultimately contribute to minimizing its side effects.
          3-bromopyruvate      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
                    Biological
                    Regulation		 Up-regulation ROS generation
                    In-vitro Model PEO1 CVCL_2686 BRCA2 syndrome Homo sapiens
SK-OV-3 CVCL_0532 Ovarian serous cystadenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Delphinidin increases the sensitivity of ovarian cancer cell lines to 3-bromopyruvate.
Target and Pathway
Target(s) Vascular endothelial growth factor receptor 2 (KDR)  Molecule Info  [1]
KEGG Pathway Ras signaling pathway Click to Show/Hide
2 Rap1 signaling pathway
3 Cytokine-cytokine receptor interaction
4 Endocytosis
5 PI3K-Akt signaling pathway
6 VEGF signaling pathway
7 Focal adhesion
8 Proteoglycans in cancer
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
Panther Pathway Angiogenesis Click to Show/Hide
2 VEGF signaling pathway
Pathway Interaction Database HIF-2-alpha transcription factor network Click to Show/Hide
2 Beta3 integrin cell surface interactions
3 Signaling events mediated by TCPTP
4 SHP2 signaling
5 S1P1 pathway
6 VEGF and VEGFR signaling network
7 Integrins in angiogenesis
8 Signaling events mediated by VEGFR1 and VEGFR2
9 Notch-mediated HES/HEY network
Reactome Neurophilin interactions with VEGF and VEGFR Click to Show/Hide
2 VEGF binds to VEGFR leading to receptor dimerization
3 Integrin cell surface interactions
4 EPHA-mediated growth cone collapse
5 VEGFA-VEGFR2 Pathway
6 VEGFR2 mediated cell proliferation
WikiPathways Focal Adhesion Click to Show/Hide
2 Nifedipine Activity
3 Cardiac Progenitor Differentiation
4 Signaling by VEGF
5 Angiogenesis
References
Reference 1 Delphinidin, a dietary anthocyanidin, inhibits vascular endothelial growth factor receptor-2 phosphorylation. Carcinogenesis. 2006 May;27(5):989-96.
Reference 2 Delphinidin sensitizes prostate cancer cells to TRAIL-induced apoptosis, by inducing DR5 and causing caspase-mediated HDAC3 cleavage. Oncotarget. 2015 Apr 30;6(12):9970-84.
Reference 3 Enhanced cytotoxic effects of arsenite in combination with anthocyanidin compound, delphinidin, against a human leukemia cell line, HL-60. Chem Biol Interact. 2018 Oct 1;294:9-17.
Reference 4 Delphinidin Increases the Sensitivity of Ovarian Cancer Cell Lines to 3-Bromopyruvate. Int J Mol Sci. 2021 Jan 12;22(2):709.
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