Natural Product (NP) Details

General Information of the NP (ID: NP8133)
Name
Cucurbitacin I
Synonyms
Cucurbitacin I; 2222-07-3; Elatericin B; Cucurbitacine (I); 1,2-Dehydroelatericin A; UNII-SHQ47990PH; CHEBI:3947; SHQ47990PH; (8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione; JSI-124; NSC521777; NSC 521777; NSC-521777; MLS002702902; 19-nor-9.beta.,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-; JSI 124; 19-Norlanosta-1,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.)- (VA; EINECS 218-736-8; NSC 112167; CUCURBITACCINE (I); CHEMBL387737; SCHEMBL2523066; SCHEMBL15914446; DTXSID501015546; HY-N1405; ZINC4097803; LMST01010110; NSC112167; AKOS024456675; CS-5431; NCGC00388208-02; 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-; 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)-; 2,16alpha,20,25-Tetrahydroxy-9beta-methyl-10alpha-19-norlanosta-1,5,23(E)-triene-3,11,22-trione; A4512; C08800; 222C073; Q27106265; (4R,9beta,16alpha,23E)-2,16,20,25-tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene-1,11,22-trione; (8S,9R,10R,13R,14S,16R,17R)-17-[(E,1R)-1,5-dihydroxy-1,5-dimethyl-2-oxo-hex-3-enyl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione; (9?,10?,16?,23E)-2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione; 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-; 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)- (VAN) (9CI)
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Species Origin Citrullus lanatus ...     Click to Show/Hide
Citrullus lanatus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Cucurbitales
Family: Cucurbitaceae
Genus: Citrullus
Species: Citrullus lanatus
Disease Ovarian cancer [ICD-11: 2C73] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C30H42O7
PubChem CID
5281321
Canonical SMILES
CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2C=C(C1=O)O)C)C)C(C)(C(=O)C=CC(C)(C)O)O)O)C)C
InChI
1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1
InChIKey
NISPVUDLMHQFRQ-MKIKIEMVSA-N
CAS Number
CAS 2222-07-3
ChEBI ID
CHEBI:3947
Herb ID
HBIN021855
SymMap ID
SMIT04988
TCMSP ID
MOL002806
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Ionizing radiation      Renal Insufficiency     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
                    In-vitro Model Cells derived from NSCLC patients Non-small cell lung cancer Homo sapiens
                    Experimental
                    Result(s)		 Targeting STAT3 signaling in CD133-positive NSCLC cells with cucurbitacin I suppressed CSC-like properties and enhanced chemoradiotherapy response.
          5-fluorouracil      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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model COLO 205 CVCL_0218 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Cucurbitacin I inhibits cell migration and invasion and enhances chemosensitivity in colon cancer.
Target and Pathway
Target(s) Apoptosis regulator Bcl-xL (BCL-xL)  Molecule Info  [2]
Bcl2 antagonist of cell death (BAD)  Molecule Info  [2]
Inositol-3-phosphate synthase 1 (SPAG9)  Molecule Info  [4]
Nuclear factor erythroid 2-related factor 2 (Nrf2)  Molecule Info  [4]
STAT factor 3 (STAT3)  Molecule Info  [2]
Stress-activated protein kinase 2a (SAPK2A)  Molecule Info  [4]
KEGG Pathway Ras signaling pathway Click to Show/Hide
2 NF-kappa B signaling pathway
3 PI3K-Akt signaling pathway
4 Apoptosis
5 Jak-STAT signaling pathway
6 Amyotrophic lateral sclerosis (ALS)
7 Toxoplasmosis
8 HTLV-I infection
9 Pathways in cancer
10 Transcriptional misregulation in cancer
11 Pancreatic cancer
12 Chronic myeloid leukemia
13 Small cell lung cancer
14 Chemokine signaling pathway
15 HIF-1 signaling pathway
16 FoxO signaling pathway
17 Signaling pathways regulating pluripotency of stem cells
18 Prolactin signaling pathway
19 Adipocytokine signaling pathway
20 Hepatitis C
21 Hepatitis B
22 Measles
23 Epstein-Barr virus infection
24 Viral carcinogenesis
25 Proteoglycans in cancer
26 MicroRNAs in cancer
27 Acute myeloid leukemia
28 Inflammatory bowel disease (IBD)
29 Protein processing in endoplasmic reticulum
30 MAPK signaling pathway
31 Rap1 signaling pathway
32 Sphingolipid signaling pathway
33 Adrenergic signaling in cardiomyocytes
34 VEGF signaling pathway
35 Osteoclast differentiation
36 Platelet activation
37 Toll-like receptor signaling pathway
38 NOD-like receptor signaling pathway
39 RIG-I-like receptor signaling pathway
40 T cell receptor signaling pathway
41 Fc epsilon RI signaling pathway
42 TNF signaling pathway
43 Leukocyte transendothelial migration
44 Neurotrophin signaling pathway
45 Retrograde endocannabinoid signaling
46 Dopaminergic synapse
47 Inflammatory mediator regulation of TRP channels
48 GnRH signaling pathway
49 Progesterone-mediated oocyte maturation
50 Epithelial cell signaling in Helicobacter pylori infection
51 Shigellosis
52 Salmonella infection
53 Pertussis
54 Leishmaniasis
55 Chagas disease (American trypanosomiasis)
56 Tuberculosis
57 Influenza A
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
2 TGF_beta_Receptor Signaling Pathway
3 Notch Signaling Pathway
4 IL5 Signaling Pathway
5 FSH Signaling Pathway
6 TCR Signaling Pathway
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 CCKR signaling map ST
3 Angiogenesis
4 EGF receptor signaling pathway
5 Inflammation mediated by chemokine and cytokine signaling pathway
6 Interleukin signaling pathway
7 JAK/STAT signaling pathway
8 PDGF signaling pathway
9 Ras Pathway
10 Alzheimer disease-amyloid secretase pathway
11 B cell activation
12 FGF signaling pathway
13 Interferon-gamma signaling pathway
14 Oxidative stress response
15 Parkinson disease
16 TGF-beta signaling pathway
17 Toll receptor signaling pathway
18 VEGF signaling pathway
19 p53 pathway feedback loops 2
20 p38 MAPK pathway
Pathwhiz Pathway Fc Epsilon Receptor I Signaling in Mast Cells Click to Show/Hide
Pathway Interaction Database IL2 signaling events mediated by PI3K Click to Show/Hide
2 IL3-mediated signaling events
3 Caspase Cascade in Apoptosis
4 EPO signaling pathway
5 IL2 signaling events mediated by STAT5
6 GMCSF-mediated signaling events
7 IL27-mediated signaling events
8 Signaling events mediated by PTP1B
9 IL12-mediated signaling events
10 Signaling events mediated by TCPTP
11 Signaling events mediated by HDAC Class I
12 IL2-mediated signaling events
13 CXCR4-mediated signaling events
14 EGF receptor (ErbB1) signaling pathway
15 IFN-gamma pathway
16 ErbB1 downstream signaling
17 ErbB2/ErbB3 signaling events
18 IL6-mediated signaling events
19 PDGFR-beta signaling pathway
20 Neurotrophic factor-mediated Trk receptor signaling
21 IL23-mediated signaling events
22 Signaling events mediated by Stem cell factor receptor (c-Kit)
23 FGF signaling pathway
24 RAC1 signaling pathway
25 Notch-mediated HES/HEY network
26 IL12 signaling mediated by STAT4
27 Endothelins
28 BCR signaling pathway
29 p73 transcription factor network
30 p38 MAPK signaling pathway
31 Atypical NF-kappaB pathway
32 IL4-mediated signaling events
33 CD40/CD40L signaling
34 Regulation of p38-alpha and p38-beta
35 CDC42 signaling events
36 Angiopoietin receptor Tie2-mediated signaling
37 FAS (CD95) signaling pathway
38 Thromboxane A2 receptor signaling
39 Role of Calcineurin-dependent NFAT signaling in lymphocytes
40 Glucocorticoid receptor regulatory network
41 Rapid glucocorticoid signaling
42 Regulation of Androgen receptor activity
43 ATF-2 transcription factor network
44 p38 signaling mediated by MAPKAP kinases
45 Retinoic acid receptors-mediated signaling
46 CXCR3-mediated signaling events
47 Signaling mediated by p38-alpha and p38-beta
48 Signaling events mediated by VEGFR1 and VEGFR2
49 p53 pathway
50 S1P2 pathway
51 Trk receptor signaling mediated by the MAPK pathway
52 VEGFR3 signaling in lymphatic endothelium
53 Regulation of retinoblastoma protein
Reactome BH3-only proteins associate with and inactivate anti-apoptotic BCL-2 members Click to Show/Hide
2 The NLRP1 inflammasome
3 Interleukin-6 signaling
4 Senescence-Associated Secretory Phenotype (SASP)
5 POU5F1 (OCT4), SOX2, NANOG activate genes related to proliferation
6 Transcriptional regulation of pluripotent stem cells
7 Growth hormone receptor signaling
8 NOD1/2 Signaling Pathway
9 p38MAPK events
10 ERK/MAPK targets
11 Activation of PPARGC1A (PGC-1alpha) by phosphorylation
12 Oxidative Stress Induced Senescence
13 CDO in myogenesis
14 DSCAM interactions
15 ADP signalling through P2Y purinoceptor 1
16 Platelet sensitization by LDL
17 VEGFA-VEGFR2 Pathway
18 activated TAK1 mediates p38 MAPK activation
19 Activation of the AP-1 family of transcription factors
20 KSRP (KHSRP) binds and destabilizes mRNA
WikiPathways IL-6 signaling pathway Click to Show/Hide
2 IL-3 Signaling Pathway
3 Nucleotide-binding domain, leucine rich repeat containing receptor (NLR) signaling pathways
4 Apoptosis
5 Amyotrophic lateral sclerosis (ALS)
6 TNF alpha Signaling Pathway
7 IL-7 Signaling Pathway
8 Leptin signaling pathway
9 Intrinsic Pathway for Apoptosis
10 Apoptosis Modulation and Signaling
11 Serotonin Receptor 2 and STAT3 Signaling
12 Notch Signaling Pathway
13 Interferon type I signaling pathways
14 EPO Receptor Signaling
15 TGF Beta Signaling Pathway
16 IL-2 Signaling Pathway
17 EGF/EGFR Signaling Pathway
18 IL-4 Signaling Pathway
19 Signaling of Hepatocyte Growth Factor Receptor
20 Kit receptor signaling pathway
21 Nuclear Receptors Meta-Pathway
22 Estrogen Receptor Pathway
23 TCA Cycle Nutrient Utilization and Invasiveness of Ovarian Cancer
24 Dopaminergic Neurogenesis
25 Transcriptional regulation of pluripotent stem cells
26 Mammary gland development pathway - Involution (Stage 4 of 4)
27 Signaling by SCF-KIT
28 Interleukin-6 signaling
29 Growth hormone receptor signaling
30 JAK/STAT
31 PDGF Pathway
32 BDNF signaling pathway
33 Oncostatin M Signaling Pathway
34 Adipogenesis
35 Interleukin-11 Signaling Pathway
36 AGE/RAGE pathway
37 Prostate Cancer
38 TSLP Signaling Pathway
39 IL-9 Signaling Pathway
40 IL17 signaling pathway
41 Regulation of Microtubule Cytoskeleton
42 TSH signaling pathway
43 Cell Differentiation - Index
44 Cell Differentiation - meta
45 Signaling by PDGF
46 NGF signalling via TRKA from the plasma membrane
47 TFs Regulate miRNAs related to cardiac hypertrophy
48 MicroRNAs in cardiomyocyte hypertrophy
49 Physiological and Pathological Hypertrophy of the Heart
50 Androgen receptor signaling pathway
51 IL-5 Signaling Pathway
52 Oxidative Stress
53 Transcriptional activation by NRF2
54 NRF2 pathway
55 Aryl Hydrocarbon Receptor Pathway
56 Mesodermal Commitment Pathway
57 Aryl Hydrocarbon Receptor
58 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
59 Arylhydrocarbon receptor (AhR) signaling pathway
60 Toll-like receptor signaling pathway
61 Monoamine Transport
62 Serotonin HTR1 Group and FOS Pathway
63 TCR Signaling Pathway
64 Senescence and Autophagy in Cancer
65 Insulin Signaling
66 MAPK Cascade
67 p38 MAPK Signaling Pathway
68 MAPK Signaling Pathway
69 TGF beta Signaling Pathway
70 Cardiac Hypertrophic Response
71 MAP kinase activation in TLR cascade
72 Regulation of mRNA Stability by Proteins that Bind AU-rich Elements
73 Nanoparticle-mediated activation of receptor signaling
74 Structural Pathway of Interleukin 1 (IL-1)
75 Alpha 6 Beta 4 signaling pathway
76 Cardiac Progenitor Differentiation
77 Integrated Pancreatic Cancer Pathway
78 Parkinsons Disease Pathway
79 Corticotropin-releasing hormone
80 B Cell Receptor Signaling Pathway
81 TWEAK Signaling Pathway
82 FSH signaling pathway
83 RANKL/RANK Signaling Pathway
84 miR-targeted genes in muscle cell - TarBase
85 miR-targeted genes in lymphocytes - TarBase
86 miR-targeted genes in leukocytes - TarBase
87 miR-targeted genes in epithelium - TarBase
88 IL-1 signaling pathway
89 Signal amplification
90 Platelet homeostasis
91 Myogenesis
92 DSCAM interactions
93 Angiogenesis
94 Regulation of toll-like receptor signaling pathway
References
Reference 1 Cucurbitacin I induces apoptosis in ovarian cancer cells through oxidative stress and the p190B?Rac1 signaling axis. Mol Med Rep. 2020 Sep;22(3):2545-2550.
Reference 2 Cucurbitacin I inhibits tumorigenic ability and enhances radiochemosensitivity in nonsmall cell lung cancer-derived CD133-positive cells. Cancer. 2011 Jul 1;117(13):2970-85.
Reference 3 Cucurbitacin I inhibits cell migration and invasion and enhances chemosensitivity in colon cancer. Oncol Rep. 2015 Apr;33(4):1867-71.
Reference 4 Low nanomolar concentrations of Cucurbitacin-I induces G2/M phase arrest and apoptosis by perturbing redox homeostasis in gastric cancer cells in vitro and in vivo. Cell Death Dis. 2016 Feb 18;7(2):e2106.
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