Natural Product (NP) Details

General Information of the NP (ID: NP0551)
Name
Oridonin
Synonyms
Oridonin; 28957-04-2; ISODONOL; Oridonine; UNII-0APJ98UCLQ; Rubescensin A; 0APJ98UCLQ; Rubescensin; Oridonin A; Kaur-16-en-15-one, 7,20-epoxy-1,6,7,14-tetrahydroxy-, (1alpha,6beta,7alpha,14R)-; NSC 250682; Curator_000006; CHEMBL1164920; SCHEMBL19217133; CHEBI:138236; HY-N0004; ZINC12661785; (14R)-7-alpha,20-Epoxy-1-alpha,6-beta,7,14-tetrahydroxykaur-16-en-15-one; AKOS025310967; CCG-208386; (1-alpha,6-beta,7-alpha,14R)-7,20-Epoxy-1,6,7,14-tetrahydroxykaur-16-en-15-one; AS-15421; P269; AB0016908; CS-0007086; 957O042; Q27236543; 7?,20-Epoxy-1?,6?,7,14-tetrahydroxykaur-16-en-15-one; (1alpha,6beta,7alpha,14R)-7,20-epoxy-1,6,7,14-tetrahydroxykaur-16-en-15-one; Kaur-16-en-15-one, 7,20-epoxy-1,6,7,14-tetrahydroxy-, (1a,6b,7a,14R)-; KAUR-16-EN-15-ONE, 7-alpha,20-EPOXY-1-alpha,6-beta,7,14-TETRAHYDROXY-, (14R)-; (1alpha,5beta,6beta,7alpha,8alpha,9beta,10alpha,13alpha,14R)-1,6,7,14-tetrahydroxy-7,20-epoxykaur-16-en-15-one; (1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-7-one
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Species Origin Isodon rubescens ...     Click to Show/Hide
Isodon rubescens
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Isodon
Species: Isodon rubescens
Disease Stomach cancer [ICD-11: 2B72] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.59
 
MDCK Permeability
 -4.968
 
PAMPA
 +++
 
HIA
 +++
 
Distribution
VDss
 -0.206
 
PPB
 48.3%
 
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
 4.581
 
T1/2
 2.562
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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Formula
C20H28O6
PubChem CID
5321010
Canonical SMILES
CC1(CCC(C23C1C(C(C45C2CCC(C4O)C(=C)C5=O)(OC3)O)O)O)C
InChI
1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1
InChIKey
SDHTXBWLVGWJFT-XKCURVIJSA-N
CAS Number
CAS 28957-04-2
ChEBI ID
CHEBI:138236
Herb ID
HBIN038254
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cetuximab      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		 Up-regulation Expression BECN1  Molecule Info 
Pathway MAP
Up-regulation Expression MAP1LC3A  Molecule Info 
Pathway MAP
Up-regulation Expression mTOR  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation mTOR  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Up-regulation Expression PRKAA2  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation PRKAA2  Molecule Info 
Pathway MAP
                    In-vitro Model HEp-2 CVCL_1906 Laryngeal carcinoma Homo sapiens
Tu 212 CVCL_4915 Head and neck squamous cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Autophagy might be strongly associated with the antitumor efficacy of ORI/Cet, which may be beneficial to the clinical application of ORI/Cet in LSCC treatment ORI/Cet in LSCC treatment.
          Imatinib      Mantle cell lymphoma     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 AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression c-RAF  Molecule Info 
Pathway MAP
Down-regulation Expression JTK8  Molecule Info 
Pathway MAP
Down-regulation Expression MEK1  Molecule Info 
Pathway MAP
Down-regulation Expression mTOR  Molecule Info 
Pathway MAP
Down-regulation Expression STAT5B  Molecule Info 
Pathway MAP
                    In-vitro Model SUP-B15 CVCL_0103 B acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)		 Oridonin in combination with imatinib exerts synergetic anti-leukemia effect in Ph+ acute lymphoblastic leukemia cells in vitro by inhibiting activation of LYN/mTOR signaling pathway.
Target and Pathway
Target(s) Caterpiller protein 1.1 (NLRP3)  Molecule Info  [4]
CDK-interacting protein 1 (CDKN1A)  Molecule Info  [5]
DNA-binding factor KBF1 (p105)  Molecule Info  [4]
Fatty acid synthase (FASN)  Molecule Info  [6]
Nuclear factor erythroid 2-related factor 2 (Nrf2)  Molecule Info  [4]
PPAR-gamma (PPARG)  Molecule Info  [7]
Protein kinase B alpha (AKT1)  Molecule Info  [5]
Transcription factor MafG (IFRD1)  Molecule Info  [8]
BioCyc Fatty acid biosynthesis initiation Click to Show/Hide
2 Fatty acid elongation -- saturated
3 Palmitate biosynthesis
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 ErbB signaling pathway
3 Ras signaling pathway
4 Rap1 signaling pathway
5 cGMP-PKG signaling pathway
6 cAMP signaling pathway
7 Chemokine signaling pathway
8 HIF-1 signaling pathway
9 FoxO signaling pathway
10 Sphingolipid signaling pathway
11 mTOR signaling pathway
12 PI3K-Akt signaling pathway
13 AMPK signaling pathway
14 Apoptosis
15 Adrenergic signaling in cardiomyocytes
16 VEGF signaling pathway
17 Osteoclast differentiation
18 Focal adhesion
19 Tight junction
20 Signaling pathways regulating pluripotency of stem cells
21 Platelet activation
22 Toll-like receptor signaling pathway
23 Jak-STAT signaling pathway
24 T cell receptor signaling pathway
25 B cell receptor signaling pathway
26 Fc epsilon RI signaling pathway
27 Fc gamma R-mediated phagocytosis
28 TNF signaling pathway
29 Neurotrophin signaling pathway
30 Cholinergic synapse
31 Dopaminergic synapse
32 Insulin signaling pathway
33 Progesterone-mediated oocyte maturation
34 Estrogen signaling pathway
35 Prolactin signaling pathway
36 Thyroid hormone signaling pathway
37 Adipocytokine signaling pathway
38 Glucagon signaling pathway
39 Regulation of lipolysis in adipocytes
40 Non-alcoholic fatty liver disease (NAFLD)
41 Carbohydrate digestion and absorption
42 Chagas disease (American trypanosomiasis)
43 Toxoplasmosis
44 Tuberculosis
45 Hepatitis C
46 Hepatitis B
47 Measles
48 Influenza A
49 HTLV-I infection
50 Epstein-Barr virus infection
51 Pathways in cancer
52 Proteoglycans in cancer
53 Colorectal cancer
54 Renal cell carcinoma
55 Pancreatic cancer
56 Endometrial cancer
57 Glioma
58 Prostate cancer
59 Melanoma
60 Chronic myeloid leukemia
61 Acute myeloid leukemia
62 Small cell lung cancer
63 Non-small cell lung cancer
64 Central carbon metabolism in cancer
65 Choline metabolism in cancer
66 Protein processing in endoplasmic reticulum
67 Fatty acid biosynthesis
68 Metabolic pathways
69 Fatty acid metabolism
70 PPAR signaling pathway
71 Huntington's disease
72 Transcriptional misregulation in cancer
73 Thyroid cancer
74 NF-kappa B signaling pathway
75 NOD-like receptor signaling pathway
76 RIG-I-like receptor signaling pathway
77 Cytosolic DNA-sensing pathway
78 Cocaine addiction
79 Epithelial cell signaling in Helicobacter pylori infection
80 Shigellosis
81 Salmonella infection
82 Pertussis
83 Legionellosis
84 Leishmaniasis
85 Amoebiasis
86 Herpes simplex infection
87 Viral carcinogenesis
88 MicroRNAs in cancer
89 Inflammatory bowel disease (IBD)
NetPath Pathway TSH Signaling Pathway Click to Show/Hide
2 IL5 Signaling Pathway
3 IL1 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 Leptin Signaling Pathway
6 TCR Signaling Pathway
7 IL2 Signaling Pathway
8 TNFalpha Signaling Pathway
Panther Pathway Angiogenesis Click to Show/Hide
2 Apoptosis signaling pathway
3 EGF receptor signaling pathway
4 Endothelin signaling pathway
5 FGF signaling pathway
6 Huntington disease
7 Hypoxia response via HIF activation
8 Inflammation mediated by chemokine and cytokine signaling pathway
9 Insulin/IGF pathway-protein kinase B signaling cascade
10 Interleukin signaling pathway
11 PI3 kinase pathway
12 T cell activation
13 VEGF signaling pathway
14 p53 pathway
15 Ras Pathway
16 p53 pathway by glucose deprivation
17 p53 pathway feedback loops 2
18 CCKR signaling map ST
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
2 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
3 Fc Epsilon Receptor I Signaling in Mast Cells
4 Insulin Signalling
5 Leucine Stimulation on Insulin Signaling
6 Fatty Acid Biosynthesis
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Fc-epsilon receptor I signaling in mast cells
3 Endothelins
4 BCR signaling pathway
5 LPA receptor mediated events
6 Insulin Pathway
7 IL4-mediated signaling events
8 TCR signaling in na&#xef
9
10 Plasma membrane estrogen receptor signaling
11 CD40/CD40L signaling
12 Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met)
13 Signaling events mediated by PTP1B
14 S1P3 pathway
15 Coregulation of Androgen receptor activity
16 Reelin signaling pathway
17 Integrin-linked kinase signaling
18 TCR signaling in na&#xef
19
20 Angiopoietin receptor Tie2-mediated signaling
21 FAS (CD95) signaling pathway
22 Thromboxane A2 receptor signaling
23 Regulation of Telomerase
24 FOXA2 and FOXA3 transcription factor networks
25 Glucocorticoid receptor regulatory network
26 mTOR signaling pathway
27 CXCR4-mediated signaling events
28 IGF1 pathway
29 FoxO family signaling
30 IL2 signaling events mediated by PI3K
31 Ceramide signaling pathway
32 p75(NTR)-mediated signaling
33 E-cadherin signaling in the nascent adherens junction
34 amb2 Integrin signaling
35 Integrins in angiogenesis
36 IFN-gamma pathway
37 ErbB1 downstream signaling
38 ErbB2/ErbB3 signaling events
39 IL6-mediated signaling events
40 E-cadherin signaling in keratinocytes
41 Nephrin/Neph1 signaling in the kidney podocyte
42 Retinoic acid receptors-mediated signaling
43 IL8- and CXCR2-mediated signaling events
44 Signaling events mediated by the Hedgehog family
45 Nongenotropic Androgen signaling
46 Hedgehog signaling events mediated by Gli proteins
47 Caspase Cascade in Apoptosis
48 CXCR3-mediated signaling events
49 VEGFR1 specific signals
50 Signaling events mediated by Stem cell factor receptor (c-Kit)
51 Signaling events mediated by VEGFR1 and VEGFR2
52 a6b1 and a6b4 Integrin signaling
53 Aurora A signaling
54 Insulin-mediated glucose transport
55 Class I PI3K signaling events mediated by Akt
56 IL8- and CXCR1-mediated signaling events
57 HIF-1-alpha transcription factor network
58 p53 pathway
59 Trk receptor signaling mediated by PI3K and PLC-gamma
60 VEGFR3 signaling in lymphatic endothelium
61 FGF signaling pathway
62 p73 transcription factor network
63 Validated transcriptional targets of deltaNp63 isoforms
64 Noncanonical Wnt signaling pathway
65 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
66 Signaling events mediated by HDAC Class I
67 RXR and RAR heterodimerization with other nuclear receptor
68 Regulation of retinoblastoma protein
69 Atypical NF-kappaB pathway
70 Canonical NF-kappaB pathway
71 IL12-mediated signaling events
72 Alternative NF-kappaB pathway
73 Osteopontin-mediated events
74 IL1-mediated signaling events
75 TNF receptor signaling pathway
76 IL23-mediated signaling events
77 HIV-1 Nef: Negative effector of Fas and TNF-alpha
78 EPO signaling pathway
Reactome Activation of BAD and translocation to mitochondria Click to Show/Hide
2 GPVI-mediated activation cascade
3 PIP3 activates AKT signaling
4 Translocation of GLUT4 to the plasma membrane
5 Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
6 AKT phosphorylates targets in the cytosol
7 AKT phosphorylates targets in the nucleus
8 Negative regulation of the PI3K/AKT network
9 eNOS activation
10 AKT-mediated inactivation of FOXO1A
11 Integrin alphaIIb beta3 signaling
12 Deactivation of the beta-catenin transactivating complex
13 CD28 dependent PI3K/Akt signaling
14 CTLA4 inhibitory signaling
15 G beta:gamma signalling through PI3Kgamma
16 KSRP (KHSRP) binds and destabilizes mRNA
17 VEGFR2 mediated vascular permeability
18 TP53 Regulates Metabolic Genes
19 Constitutive Signaling by AKT1 E17K in Cancer
20 ChREBP activates metabolic gene expression
21 Activation of gene expression by SREBF (SREBP)
22 Fatty Acyl-CoA Biosynthesis
23 PPARA activates gene expression
24 Transcriptional regulation of white adipocyte differentiation
25 Nuclear Receptor transcription pathway
26 Activation of NF-kappaB in B cells
27 RIP-mediated NFkB activation via ZBP1
28 Regulated proteolysis of p75NTR
29 NF-kB is activated and signals survival
30 Senescence-Associated Secretory Phenotype (SASP)
31 FCERI mediated NF-kB activation
32 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
33 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
34 Interleukin-1 processing
35 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
36 IkBA variant leads to EDA-ID
37 CLEC7A (Dectin-1) signaling
38 CD209 (DC-SIGN) signaling
39 CLEC7A/inflammasome pathway
40 MAP3K8 (TPL2)-dependent MAPK1/3 activation
41 TRAF6 mediated NF-kB activation
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 DNA Damage Response (only ATM dependent)
3 TCR Signaling Pathway
4 Notch Signaling Pathway
5 EPO Receptor Signaling
6 IL-2 Signaling Pathway
7 Insulin Signaling
8 Endochondral Ossification
9 EGF/EGFR Signaling Pathway
10 IL-4 Signaling Pathway
11 TGF beta Signaling Pathway
12 IL-6 signaling pathway
13 Wnt Signaling Pathway Netpath
14 Copper homeostasis
15 Extracellular vesicle-mediated signaling in recipient cells
16 Apoptosis-related network due to altered Notch3 in ovarian cancer
17 IL-3 Signaling Pathway
18 Cardiac Hypertrophic Response
19 Translocation of GLUT4 to the Plasma Membrane
20 Regulation of mRNA Stability by Proteins that Bind AU-rich Elements
21 PIP3 activates AKT signaling
22 Signal Transduction of S1P Receptor
23 T-Cell Receptor and Co-stimulatory Signaling
24 Primary Focal Segmental Glomerulosclerosis FSGS
25 Apoptosis
26 Alpha 6 Beta 4 signaling pathway
27 BDNF signaling pathway
28 Integrated Pancreatic Cancer Pathway
29 Oncostatin M Signaling Pathway
30 Corticotropin-releasing hormone
31 Interleukin-11 Signaling Pathway
32 AGE/RAGE pathway
33 TNF alpha Signaling Pathway
34 B Cell Receptor Signaling Pathway
35 Prostate Cancer
36 Signaling Pathways in Glioblastoma
37 TSLP Signaling Pathway
38 IL17 signaling pathway
39 IL-7 Signaling Pathway
40 Regulation of Microtubule Cytoskeleton
41 TWEAK Signaling Pathway
42 FSH signaling pathway
43 Leptin signaling pathway
44 TSH signaling pathway
45 RANKL/RANK Signaling Pathway
46 Integrated Breast Cancer Pathway
47 SREBP signalling
48 Integrated Cancer pathway
49 IL-1 signaling pathway
50 Metabolism of nitric oxide
51 Integrin-mediated Cell Adhesion
52 TFs Regulate miRNAs related to cardiac hypertrophy
53 MicroRNAs in cardiomyocyte hypertrophy
54 Angiogenesis
55 TOR Signaling
56 Regulation of toll-like receptor signaling pathway
57 AMPK Signaling
58 Androgen receptor signaling pathway
59 IL-5 Signaling Pathway
60 Oxidative Stress
61 Transcriptional activation by NRF2
62 NRF2 pathway
63 Nuclear Receptors Meta-Pathway
64 Aryl Hydrocarbon Receptor Pathway
65 Mesodermal Commitment Pathway
66 Aryl Hydrocarbon Receptor
67 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
68 Arylhydrocarbon receptor (AhR) signaling pathway
69 Fatty Acid Biosynthesis
70 Liver X Receptor Pathway
71 Activation of Gene Expression by SREBP (SREBF)
72 SREBF and miR33 in cholesterol and lipid homeostasis
73 Metabolism of water-soluble vitamins and cofactors
74 Integration of energy metabolism
75 Fatty acid, triacylglycerol, and ketone body metabolism
76 Nuclear Receptors in Lipid Metabolism and Toxicity
77 Differentiation of white and brown adipocyte
78 Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
79 Transcriptional Regulation of White Adipocyte Differentiation
80 Adipogenesis
81 Nuclear Receptors
82 SIDS Susceptibility Pathways
83 TGF Beta Signaling Pathway
84 Apoptosis Modulation by HSP70
85 MAPK Signaling Pathway
86 Myometrial Relaxation and Contraction Pathways
87 IL1 and megakaryotyces in obesity
88 Hair Follicle Development: Cytodifferentiation (Part 3 of 3)
89 Hair Follicle Development: Organogenesis (Part 2 of 3)
90 Hair Follicle Development: Induction (Part 1 of 3)
91 Selenium Metabolism and Selenoproteins
92 Cytosolic sensors of pathogen-associated DNA
93 Fc epsilon receptor (FCERI) signaling
94 Signaling by the B Cell Receptor (BCR)
95 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
96 Structural Pathway of Interleukin 1 (IL-1)
97 EBV LMP1 signaling
98 Neural Crest Differentiation
99 Signalling by NGF
100 TCR signaling
101 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
102 Interleukin-1 signaling
103 Interleukin-1 processing
104 Apoptosis Modulation and Signaling
105 Folate Metabolism
106 Vitamin B12 Metabolism
107 Selenium Micronutrient Network
108 Osteopontin Signaling
References
Reference 1 [Inhibitory effect of Oridonin injection on heterotransplanted gastric adenocarcinoma in nude mice and its mechanism]. Zhonghua Zhong Liu Za Zhi. 2008 Feb;30(2):89-92.
Reference 2 Molecular mechanisms of apoptosis and autophagy elicited by combined treatment with oridonin and cetuximab in laryngeal squamous cell carcinoma. Apoptosis. 2019 Feb;24(1-2):33-45.
Reference 3 Oridonin in combination with imatinib exerts synergetic anti-leukemia effect in Ph+ acute lymphoblastic leukemia cells in vitro by inhibiting activation of LYN/mTOR signaling pathway. Cancer Biol Ther. 2012 Nov;13(13):1244-54.
Reference 4 Oridonin protects LPS-induced acute lung injury by modulating Nrf2-mediated oxidative stress and Nrf2-independent NLRP3 and NF-KappaB pathways. Cell Commun Signal. 2019 Jun 11;17(1):62.
Reference 5 Oridonin protects against cardiac hypertrophy by promoting P21-related autophagy. Cell Death Dis. 2019 May 24;10(6):403.
Reference 6 The anticancer effect of oridonin is mediated by fatty acid synthase suppression in human colorectal cancer cells. J Gastroenterol. 2013 Feb;48(2):182-92.
Reference 7 Oridonin exerts anticancer effect on osteosarcoma by activating PPAR-Gamma and inhibiting Nrf2 pathway. Cell Death Dis. 2018 Jan 11;9(1):15.
Reference 8 A Novel Diterpenoid Suppresses Osteoclastogenesis and Promotes Osteogenesis by Inhibiting Ifrd1-Mediated and IKappaBAlpha-Mediated p65 Nuclear Translocation. J Bone Miner Res. 2018 Apr;33(4):667-678.
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