Natural Product (NP) Details

General Information of the NP (ID: NP1431)
Name
Orientin
Synonyms
Orientin; 28608-75-5; Lutexin; Luteolin-8-glucoside; Luteolin 8-C-glucoside; UNII-IAX93XCW6C; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-; 8-beta-D-glucosylluteolin; IAX93XCW6C; CHEBI:7781; MFCD00017432; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one; Orientin (Flavone); 8-glucosylluteolin; Orientine; Luteolin-8-C-glucoside; Luteolin 8-C-beta-D-glucopyranoside; 2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-chromen-4-one; NSC-133101; 8-beta-D-Glucopyranosyl-3',4',5,7-tetrahydroxyflavone; 2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one; SCHEMBL25942; Orientin, analytical standard; CHEMBL520866; Orientin, >=97% (HPLC); BDBM84982; DTXSID60182790; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-.beta.-D-glucopyranosyl-5,7-dihydroxy-; HMS3886J16; HY-N0405; ZINC4098560; s9099; AKOS015896746; CCG-269214; AS-73888; CS-0008937; Y0149; A12096; C10114; 608O755; A819507; Orientin, primary pharmaceutical reference standard; Q421676; Q-100362; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]-1-benzopyran-4-one; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one; 2-[3,4-bis(oxidanyl)phenyl]-8-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]-5,7-bis(oxidanyl)chromen-4-one
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Species Origin Ranunculaceae ...     Click to Show/Hide
Ranunculaceae
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Ranunculaceae
Disease Colorectal cancer [ICD-11: 2B91] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.208
 
MDCK Permeability
 -5.022
 
PAMPA
 +++
 
HIA
 ++
 
Distribution
VDss
 -0.011
 
PPB
 84.4%
 
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
 3.933
 
T1/2
 4.944
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
C21H20O11
PubChem CID
5281675
Canonical SMILES
C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O)O
InChI
1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
InChIKey
PLAPMLGJVGLZOV-VPRICQMDSA-N
CAS Number
CAS 28608-75-5
ChEBI ID
CHEBI:7781
Herb ID
HBIN038267
SymMap ID
SMIT00199
TCMSP ID
MOL004178
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          BS21      Obesity     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 Phosphorylation ACACA  Molecule Info 
Pathway MAP
Down-regulation Expression CEBPA  Molecule Info 
Pathway MAP
Up-regulation Expression CHPT1  Molecule Info 
Pathway MAP
Down-regulation Expression FABP4  Molecule Info 
Pathway MAP
Down-regulation Expression FAS  Molecule Info 
Pathway MAP
Down-regulation Expression PPAR-gamma  Molecule Info 
Pathway MAP
Up-regulation Expression PPARGC1A  Molecule Info 
Pathway MAP
Up-regulation Expression PRDM16  Molecule Info 
Pathway MAP
Up-regulation Expression PRKAA2  Molecule Info 
Pathway MAP
Down-regulation Expression SREBF1  Molecule Info 
Pathway MAP
Up-regulation Expression UCP1  Molecule Info 
Pathway MAP
Up-regulation Expression UCP2  Molecule Info 
Pathway MAP
                    In-vitro Model 3T3-L1 CVCL_0123 Healthy Mus musculus
                    Experimental
                    Result(s)		 BS21 plays a modulatory role in adipocytes by reducing adipogenesis and lipogenesis, increasing fat oxidation, and inducing browning.
Target and Pathway
Target(s) Extracellular signal-regulated kinase 1 (ERK1)  Molecule Info  [3]
Extracellular signal-regulated kinase 2 (ERK2)  Molecule Info  [3]
Stress-activated protein kinase JNK1 (JNK1)  Molecule Info  [3]
Stress-activated protein kinase JNK2 (JNK2)  Molecule Info  [3]
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 Oocyte meiosis
12 mTOR signaling pathway
13 PI3K-Akt signaling pathway
14 Adrenergic signaling in cardiomyocytes
15 Vascular smooth muscle contraction
16 Dorso-ventral axis formation
17 TGF-beta signaling pathway
18 Axon guidance
19 VEGF signaling pathway
20 Osteoclast differentiation
21 Focal adhesion
22 Adherens junction
23 Gap junction
24 Signaling pathways regulating pluripotency of stem cells
25 Platelet activation
26 Toll-like receptor signaling pathway
27 NOD-like receptor signaling pathway
28 Natural killer cell mediated cytotoxicity
29 T cell receptor signaling pathway
30 B cell receptor signaling pathway
31 Fc epsilon RI signaling pathway
32 Fc gamma R-mediated phagocytosis
33 TNF signaling pathway
34 Circadian entrainment
35 Long-term potentiation
36 Neurotrophin signaling pathway
37 Retrograde endocannabinoid signaling
38 Glutamatergic synapse
39 Cholinergic synapse
40 Serotonergic synapse
41 Long-term depression
42 Regulation of actin cytoskeleton
43 Insulin signaling pathway
44 GnRH signaling pathway
45 Progesterone-mediated oocyte maturation
46 Estrogen signaling pathway
47 Melanogenesis
48 Prolactin signaling pathway
49 Thyroid hormone signaling pathway
50 Oxytocin signaling pathway
51 Type II diabetes mellitus
52 Aldosterone-regulated sodium reabsorption
53 Alzheimer's disease
54 Prion diseases
55 Alcoholism
56 Shigellosis
57 Salmonella infection
58 Pertussis
59 Leishmaniasis
60 Chagas disease (American trypanosomiasis)
61 Toxoplasmosis
62 Tuberculosis
63 Hepatitis C
64 Hepatitis B
65 Influenza A
66 Pathways in cancer
67 Viral carcinogenesis
68 Proteoglycans in cancer
69 Colorectal cancer
70 Renal cell carcinoma
71 Pancreatic cancer
72 Endometrial cancer
73 Glioma
74 Prostate cancer
75 Thyroid cancer
76 Melanoma
77 Bladder cancer
78 Chronic myeloid leukemia
79 Acute myeloid leukemia
80 Non-small cell lung cancer
81 Central carbon metabolism in cancer
82 Choline metabolism in cancer
83 Protein processing in endoplasmic reticulum
84 Wnt signaling pathway
85 RIG-I-like receptor signaling pathway
86 Dopaminergic synapse
87 Inflammatory mediator regulation of TRP channels
88 Adipocytokine signaling pathway
89 Non-alcoholic fatty liver disease (NAFLD)
90 Epithelial cell signaling in Helicobacter pylori infection
91 HTLV-I infection
92 Herpes simplex infection
93 Epstein-Barr virus infection
94 MicroRNAs in cancer
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
2 TCR Signaling Pathway
3 TNFalpha Signaling Pathway
4 IL2 Signaling Pathway
Panther Pathway Alzheimer disease-amyloid secretase pathway Click to Show/Hide
2 Angiogenesis
3 Apoptosis signaling pathway
4 B cell activation
5 EGF receptor signaling pathway
6 Endothelin signaling pathway
7 FGF signaling pathway
8 Inflammation mediated by chemokine and cytokine signaling pathway
9 Insulin/IGF pathway-mitogen activated protein kinase kinase/MAP kinase cascade
10 Integrin signalling pathway
11 Interferon-gamma signaling pathway
12 Interleukin signaling pathway
13 PDGF signaling pathway
14 Parkinson disease
15 TGF-beta signaling pathway
16 T cell activation
17 Toll receptor signaling pathway
18 VEGF signaling pathway
19 Ras Pathway
20 Angiotensin II-stimulated signaling through G proteins and beta-arrestin
21 CCKR signaling map ST
22 FAS signaling pathway
23 Oxidative stress response
24 Huntington disease
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
Pathway Interaction Database Fc-epsilon receptor I signaling in mast cells Click to Show/Hide
2 Endothelins
3 BCR signaling pathway
4 Signaling events mediated by PRL
5 ErbB4 signaling events
6 GMCSF-mediated signaling events
7 Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met)
8 S1P3 pathway
9 EPHB forward signaling
10 Osteopontin-mediated events
11 S1P4 pathway
12 Presenilin action in Notch and Wnt signaling
13 TRAIL signaling pathway
14 CDC42 signaling events
15 Signaling events regulated by Ret tyrosine kinase
16 Angiopoietin receptor Tie2-mediated signaling
17 S1P1 pathway
18 Regulation of Telomerase
19 Netrin-mediated signaling events
20 Role of Calcineurin-dependent NFAT signaling in lymphocytes
21 Glucocorticoid receptor regulatory network
22 Arf6 downstream pathway
23 mTOR signaling pathway
24 IL2-mediated signaling events
25 EGF receptor (ErbB1) signaling pathway
26 Ras signaling in the CD4+ TCR pathway
27 Ceramide signaling pathway
28 Integrins in angiogenesis
29 IFN-gamma pathway
30 ErbB1 downstream signaling
31 ATF-2 transcription factor network
32 ErbB2/ErbB3 signaling events
33 ALK1 signaling events
34 PDGFR-beta signaling pathway
35 Neurotrophic factor-mediated Trk receptor signaling
36 Syndecan-1-mediated signaling events
37 Retinoic acid receptors-mediated signaling
38 Nongenotropic Androgen signaling
39 CXCR3-mediated signaling events
40 VEGFR1 specific signals
41 Regulation of cytoplasmic and nuclear SMAD2/3 signaling
42 Signaling events mediated by Stem cell factor receptor (c-Kit)
43 Signaling events mediated by VEGFR1 and VEGFR2
44 Syndecan-2-mediated signaling events
45 Cellular roles of Anthrax toxin
46 S1P2 pathway
47 Trk receptor signaling mediated by the MAPK pathway
48 Downstream signaling in na&#xef
49
50 VEGFR3 signaling in lymphatic endothelium
51 Alpha-synuclein signaling
52 FGF signaling pathway
53 RhoA signaling pathway
54 Noncanonical Wnt signaling pathway
55 CD40/CD40L signaling
56 Reelin signaling pathway
57 FAS (CD95) signaling pathway
58 IL1-mediated signaling events
59 Rapid glucocorticoid signaling
60 FoxO family signaling
61 Regulation of Androgen receptor activity
62 p75(NTR)-mediated signaling
63 JNK signaling in the CD4+ TCR pathway
64 Nephrin/Neph1 signaling in the kidney podocyte
65 HIV-1 Nef: Negative effector of Fas and TNF-alpha
66 EPO signaling pathway
67 Ephrin B reverse signaling
68 p53 pathway
69 N-cadherin signaling events
70 RAC1 signaling pathway
71 Signaling events mediated by focal adhesion kinase
72 Glypican 3 network
73 IL12 signaling mediated by STAT4
74 Class IB PI3K non-lipid kinase events
75 BMP receptor signaling
76 Regulation of retinoblastoma protein
Reactome MAPK3 (ERK1) activation Click to Show/Hide
2 RAF-independent MAPK1/3 activation
3 ISG15 antiviral mechanism
4 ERK/MAPK targets
5 Regulation of actin dynamics for phagocytic cup formation
6 Oxidative Stress Induced Senescence
7 Senescence-Associated Secretory Phenotype (SASP)
8 Oncogene Induced Senescence
9 FCERI mediated MAPK activation
10 Regulation of HSF1-mediated heat shock response
11 NCAM signaling for neurite out-growth
12 Activation of the AP-1 family of transcription factors
13 Thrombin signalling through proteinase activated receptors (PARs)
14 Negative regulation of FGFR1 signaling
15 Negative regulation of FGFR2 signaling
16 Negative regulation of FGFR3 signaling
17 Negative regulation of FGFR4 signaling
18 RHO GTPases Activate WASPs and WAVEs
19 RAF/MAP kinase cascade
20 MAP2K and MAPK activation
21 Negative feedback regulation of MAPK pathway
22 Negative regulation of MAPK pathway
23 Signal attenuation
24 Advanced glycosylation endproduct receptor signaling
25 Gastrin-CREB signalling pathway via PKC and MAPK
26 Growth hormone receptor signaling
27 NRAGE signals death through JNK
28 NRIF signals cell death from the nucleus
29 DSCAM interactions
30 JNK (c-Jun kinases) phosphorylation and activation mediated by activated human TAK1
31 Recruitment and ATM-mediated phosphorylation of repair and signaling proteins at DNA double strand breaks
32 MAPK1 (ERK2) activation
33 Golgi Cisternae Pericentriolar Stack Reorganization
34 Recycling pathway of L1
35 CREB phosphorylation through the activation of Ras
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 Serotonin Receptor 4/6/7 and NR3C Signaling
3 Serotonin Receptor 2 and ELK-SRF/GATA4 signaling
4 Serotonin HTR1 Group and FOS Pathway
5 TCR Signaling Pathway
6 Hypothetical Network for Drug Addiction
7 EPO Receptor Signaling
8 TGF Beta Signaling Pathway
9 Regulation of Actin Cytoskeleton
10 IL-2 Signaling Pathway
11 Insulin Signaling
12 MAPK Cascade
13 IL-4 Signaling Pathway
14 MAPK Signaling Pathway
15 IL-6 signaling pathway
16 Signaling of Hepatocyte Growth Factor Receptor
17 Kit receptor signaling pathway
18 TCA Cycle Nutrient Utilization and Invasiveness of Ovarian Cancer
19 IL-3 Signaling Pathway
20 Cardiac Hypertrophic Response
21 MAP kinase activation in TLR cascade
22 Fc epsilon receptor (FCERI) signaling
23 RAF/MAP kinase cascade
24 Structural Pathway of Interleukin 1 (IL-1)
25 Genes and (Common) Pathways Underlying Drug Addiction
26 Signal Transduction of S1P Receptor
27 PDGF Pathway
28 Alpha 6 Beta 4 signaling pathway
29 Spinal Cord Injury
30 BDNF signaling pathway
31 Integrated Pancreatic Cancer Pathway
32 Oncostatin M Signaling Pathway
33 Corticotropin-releasing hormone
34 Interleukin-11 Signaling Pathway
35 AGE/RAGE pathway
36 TNF alpha Signaling Pathway
37 Prostate Cancer
38 Signaling Pathways in Glioblastoma
39 TSLP Signaling Pathway
40 IL-9 Signaling Pathway
41 IL17 signaling pathway
42 Alzheimers Disease
43 IL-7 Signaling Pathway
44 TWEAK Signaling Pathway
45 FSH signaling pathway
46 Leptin signaling pathway
47 RANKL/RANK Signaling Pathway
48 IL-1 signaling pathway
49 Thrombin signalling through proteinase activated receptors (PARs)
50 Signaling by Insulin receptor
51 Signaling by FGFR
52 RNA Polymerase I, RNA Polymerase III, and Mitochondrial Transcription
53 L1CAM interactions
54 Advanced glycosylation endproduct receptor signaling
55 Apoptosis Modulation and Signaling
56 MicroRNAs in cardiomyocyte hypertrophy
57 Regulation of toll-like receptor signaling pathway
58 Osteopontin Signaling
59 IL-5 Signaling Pathway
60 DNA Damage Response (only ATM dependent)
61 ErbB Signaling Pathway
62 EGF/EGFR Signaling Pathway
63 TGF beta Signaling Pathway
64 FAS pathway and Stress induction of HSP regulation
65 Transcriptional activation by NRF2
66 NLR Proteins
67 Nanoparticle-mediated activation of receptor signaling
68 EBV LMP1 signaling
69 JAK/STAT
70 Nanoparticle triggered regulated necrosis
71 B Cell Receptor Signaling Pathway
72 Signalling by NGF
73 Intrinsic Pathway for Apoptosis
74 DSCAM interactions
75 Type II diabetes mellitus
76 Physiological and Pathological Hypertrophy of the Heart
77 Osteoclast Signaling
78 Vitamin A and Carotenoid Metabolism
79 Senescence and Autophagy in Cancer
80 Apoptosis-related network due to altered Notch3 in ovarian cancer
81 Bladder Cancer
82 Neurotransmitter Receptor Binding And Downstream Transmission In The Postsynaptic Cell
83 Nifedipine Activity
84 Aryl Hydrocarbon Receptor
85 Endothelin Pathways
86 Integrated Breast Cancer Pathway
87 Opioid Signalling
88 Integrin-mediated Cell Adhesion
89 Heart Development
90 Angiogenesis
91 Wnt Signaling Pathway
92 Wnt Signaling Pathway and Pluripotency
93 ATM Signaling Pathway
References
Reference 1 Orientin, a flavanoid, mitigates 1, 2 dimethylhydrazine-induced colorectal lesions in Wistar rats fed a high-fat diet. Toxicol Rep. 2018 Sep 27;5:977-987.
Reference 2 Herbal Combination of Phyllostachys pubescens and Scutellaria baicalensis Inhibits Adipogenesis and Promotes Browning via AMPK Activation in 3T3-L1 Adipocytes. Plants (Basel). 2020 Oct 23;9(11):1422.
Reference 3 Neuroprotective effects of orientin on oxygen-glucose deprivation/reperfusion-induced cell injury in primary culture of rat cortical neurons. Exp Biol Med (Maywood). 2018 Jan;243(1):78-86.
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