Natural Product (NP) Details

General Information of the NP (ID: NP3125)
Name
Procyanidin
Synonyms
2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)chroman-3,4,5,7-tetraol; 2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-3,4-dihydrochromene-3,4,5,7-tetrol; 2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl)oxy)-3,4-dihydro-; Procyanidins; 2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl]oxy]-3,4-dihydro-; BRN 1675863; 2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl)oxy)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol; 3,3',4,4',5,7-Flavanhexol, 2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-chromanyl)oxy)-; Procyanidin, Technical grade; SCHEMBL15091123; DTXSID90858698; CHEBI:166895; BCP25503; HY-N0794; C31H28O12; MFCD01662851; s5105; AKOS025402316; AC-8032; CCG-270176; CCG-270178; 2-(3,4-dihydroxyphenyl)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl]oxy-chromane-3,4,5,7-tetrol; AK321485; CS-0009805; FT-0688150; X1211; Y0170; 852P226; 2-(3,4-dihydroxyphenyl)-2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl]oxy}-3,4,5,7-chromanetetrol
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Species Origin Cinnamomum camphora ...     Click to Show/Hide
Cinnamomum camphora
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Laurales
Family: Lauraceae
Genus: Cinnamomum
Species: Cinnamomum camphora
Fagopyrum dibotrys
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Caryophyllales
Family: Polygonaceae
Genus: Fagopyrum
Species: Fagopyrum dibotrys
Flemingia macrophylla
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Flemingia
Species: Flemingia macrophylla
Disease Breast cancer [ICD-11: 2C60] Phase 2 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.559
 
MDCK Permeability
 -5.003
 
PAMPA
 +
 
HIA
 - - -
 
Distribution
VDss
 -0.023
 
PPB
 89.5%
 
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
 9.671
 
T1/2
 2.929
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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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C30H26O13
PubChem CID
107876
Canonical SMILES
C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC4(C(C(C5=C(C=C(C=C5O4)O)O)O)O)C6=CC(=C(C=C6)O)O
InChI
1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2
InChIKey
HGVVOUNEGQIPMS-UHFFFAOYSA-N
CAS Number
CAS 20347-71-1
Herb ID
HBIN040755
SymMap ID
SMIT02315
TCMSP ID
MOL003352
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     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 Caco-2 CVCL_0025 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Procyanidin enhances the impact of 5-Fluorouracil chemotherapy on Caco-2 human colon cancer cells.
Target and Pathway
Target(s) Caspase-3 (CASP3)  Molecule Info  [3]
Cellular tumor antigen p53 (TP53)  Molecule Info  [3]
DNA-binding factor KBF1 (p105)  Molecule Info  [4]
Protein kinase B alpha (AKT1)  Molecule Info  [5]
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 Cell cycle
67 p53 signaling pathway
68 Wnt signaling pathway
69 Amyotrophic lateral sclerosis (ALS)
70 Huntington's disease
71 Herpes simplex infection
72 Transcriptional misregulation in cancer
73 Viral carcinogenesis
74 MicroRNAs in cancer
75 Thyroid cancer
76 Basal cell carcinoma
77 Bladder cancer
78 Natural killer cell mediated cytotoxicity
79 Serotonergic synapse
80 Alzheimer's disease
81 Parkinson's disease
82 Epithelial cell signaling in Helicobacter pylori infection
83 Pertussis
84 Legionellosis
85 Amoebiasis
86 Viral myocarditis
87 NF-kappa B signaling pathway
88 NOD-like receptor signaling pathway
89 RIG-I-like receptor signaling pathway
90 Cytosolic DNA-sensing pathway
91 Cocaine addiction
92 Shigellosis
93 Salmonella infection
94 Leishmaniasis
95 Inflammatory bowel disease (IBD)
NetPath Pathway TSH Signaling Pathway Click to Show/Hide
2 FSH Signaling Pathway
3 TCR Signaling Pathway
4 IL2 Signaling Pathway
5 IL4 Signaling Pathway
6 IL5 Signaling Pathway
7 IL1 Signaling Pathway
8 TNFalpha Signaling Pathway
9 Leptin 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
19 Wnt signaling pathway
20 P53 pathway feedback loops 1
21 FAS signaling pathway
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
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 Signaling events mediated by HDAC Class III
63 Validated targets of C-MYC transcriptional activation
64 LKB1 signaling events
65 Direct p53 effectors
66 AP-1 transcription factor network
67 Hypoxic and oxygen homeostasis regulation of HIF-1-alpha
68 Signaling mediated by p38-alpha and p38-beta
69 BARD1 signaling events
70 PLK3 signaling events
71 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
72 Role of Calcineurin-dependent NFAT signaling in lymphocytes
73 Posttranslational regulation of adherens junction stability and dissassembly
74 HIV-1 Nef: Negative effector of Fas and TNF-alpha
75 Syndecan-2-mediated signaling events
76 Atypical NF-kappaB pathway
77 Canonical NF-kappaB pathway
78 IL12-mediated signaling events
79 Alternative NF-kappaB pathway
80 Osteopontin-mediated events
81 Signaling events mediated by HDAC Class I
82 IL1-mediated signaling events
83 TNF receptor signaling pathway
84 IL23-mediated signaling events
85 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 Activation of NOXA and translocation to mitochondria
21 Activation of PUMA and translocation to mitochondria
22 Pre-NOTCH Transcription and Translation
23 Oxidative Stress Induced Senescence
24 Formation of Senescence-Associated Heterochromatin Foci (SAHF)
25 Oncogene Induced Senescence
26 DNA Damage/Telomere Stress Induced Senescence
27 Autodegradation of the E3 ubiquitin ligase COP1
28 Recruitment and ATM-mediated phosphorylation of repair and signaling proteins at DNA double strand breaks
29 Stabilization of p53
30 Factors involved in megakaryocyte development and platelet production
31 SMAC binds to IAPs
32 SMAC-mediated dissociation of IAP:caspase complexes
33 Apoptotic cleavage of cellular proteins
34 Degradation of the extracellular matrix
35 NADE modulates death signalling
36 Activation of DNA fragmentation factor
37 Caspase-mediated cleavage of cytoskeletal proteins
38 Activation of NF-kappaB in B cells
39 RIP-mediated NFkB activation via ZBP1
40 Regulated proteolysis of p75NTR
41 NF-kB is activated and signals survival
42 Senescence-Associated Secretory Phenotype (SASP)
43 FCERI mediated NF-kB activation
44 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
45 Transcriptional regulation of white adipocyte differentiation
46 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
47 Interleukin-1 processing
48 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
49 IkBA variant leads to EDA-ID
50 CLEC7A (Dectin-1) signaling
51 CD209 (DC-SIGN) signaling
52 CLEC7A/inflammasome pathway
53 MAP3K8 (TPL2)-dependent MAPK1/3 activation
54 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 DNA Damage Response
61 ErbB Signaling Pathway
62 Senescence and Autophagy in Cancer
63 G1 to S cell cycle control
64 Sandbox Pathway
65 Wnt Signaling Pathway and Pluripotency
66 MAPK Signaling Pathway
67 Bladder Cancer
68 Mammary gland development pathway - Involution (Stage 4 of 4)
69 Pre-NOTCH Expression and Processing
70 ATM Signaling Pathway
71 Amyotrophic lateral sclerosis (ALS)
72 Retinoblastoma (RB) in Cancer
73 Spinal Cord Injury
74 Gastric cancer network 2
75 Metastatic brain tumor
76 Alzheimers Disease
77 Intrinsic Pathway for Apoptosis
78 Factors involved in megakaryocyte development and platelet production
79 Cell Cycle
80 Cell Cycle Checkpoints
81 Apoptosis Modulation and Signaling
82 Folate Metabolism
83 TP53 Network
84 Fluoropyrimidine Activity
85 miRNAs involved in DNA damage response
86 miRNA Regulation of DNA Damage Response
87 SIDS Susceptibility Pathways
88 Apoptosis Modulation by HSP70
89 FAS pathway and Stress induction of HSP regulation
90 Signaling by Hippo
91 Parkinsons Disease Pathway
92 Allograft Rejection
93 Signalling by NGF
94 Regulation of Apoptosis
95 Apoptotic execution phase
96 TGF Beta Signaling Pathway
97 Oxidative Stress
98 Myometrial Relaxation and Contraction Pathways
99 IL1 and megakaryotyces in obesity
100 Hair Follicle Development: Cytodifferentiation (Part 3 of 3)
101 Hair Follicle Development: Organogenesis (Part 2 of 3)
102 Hair Follicle Development: Induction (Part 1 of 3)
103 Selenium Metabolism and Selenoproteins
104 Cytosolic sensors of pathogen-associated DNA
105 Fc epsilon receptor (FCERI) signaling
106 Transcriptional Regulation of White Adipocyte Differentiation
107 Signaling by the B Cell Receptor (BCR)
108 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
109 Structural Pathway of Interleukin 1 (IL-1)
110 EBV LMP1 signaling
111 Aryl Hydrocarbon Receptor
112 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
113 Neural Crest Differentiation
114 TCR signaling
115 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
116 Interleukin-1 signaling
117 Interleukin-1 processing
118 Vitamin B12 Metabolism
119 Selenium Micronutrient Network
120 Osteopontin Signaling
References
Reference 1 ClinicalTrials.gov (NCT00041223) IH636 Grape Seed Extract in Treating Hardening of Breast Tissue in Women Who Have Undergone Radiation Therapy for Early Breast Cancer
Reference 2 Low molecular weight procyanidins from grape seeds enhance the impact of 5-Fluorouracil chemotherapy on Caco-2 human colon cancer cells. PLoS One. 2014 Jun 6;9(6):e98921.
Reference 3 Procyanidin from peanut skin induces antiproliferative effect in human prostate carcinoma cells DU145. Chem Biol Interact. 2018 May 25;288:12-23.
Reference 4 Proanthocyanidin alleviates doxorubicin-induced cardiac injury by inhibiting NF-kB pathway and modulating oxidative stress, cell cycle, and fibrogenesis. J Biochem Mol Toxicol. 2021 Apr;35(4):e22716.
Reference 5 Protective Effect of Proanthocyanidins in Cadmium Induced Neurotoxicity in Mice. Drug Res (Stuttg). 2015 Oct;65(10):555-60.
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