Natural Product: NPC53558
Natural Product ID:   | NPC53558 |
Common Name*:   | ODBRNZZJSYPIDI-VJXVFPJBSA-M |
IUPAC Name:   | n.a. |
Synonyms:   | |
Standard InCHIKey:   | ODBRNZZJSYPIDI-VJXVFPJBSA-M |
Standard InCHI:   | InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/p-1/t14-,17-,19+,20-,21+/m1/s1 |
SMILES:   | c1cc(c(cc1c1cc(=O)c2c(cc(c(c2O)[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)o1)O)[O-]
|
Synthetic Gene Cluster:   |
n.a. |
ChEMBL Identifier:   |
n.a. |
PubChem CID:   |
49852298 |
Chemical Classification**:   |
-
CHEMONTID:0000000 [Organic compounds]
-
[CHEMONTID:0000261] Phenylpropanoids and polyketides
-
[CHEMONTID:0000334] Flavonoids
[CHEMONTID:0001111] Flavonoid glycosides[CHEMONTID:0001737] Flavonoid C-glycosides
|
*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.
  Species Source
Organism ID |
Organism Name |
Taxonomy Level |
Family |
SuperKingdom |
Isolation Part |
Collection Location |
Collection Time |
Reference |
NPO27288 |
Citrus maxima |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
DOI[10.1016/S0031-9422(99)00119-3] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[11599360] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
fruit |
n.a. |
PMID[15577254] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[15621610] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
fruit |
n.a. |
PMID[15739361] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
root |
n.a. |
PMID[16335823] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
root |
n.a. |
PMID[16441081] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[16675659] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
seed |
n.a. |
PMID[21381697] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[22074222] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
root |
n.a. |
PMID[22074222] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
fruits |
n.a. |
n.a. |
PMID[23327905] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
seed |
n.a. |
PMID[23845552] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
rhizome |
n.a. |
PMID[23867078] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
root |
n.a. |
PMID[23867078] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
seeds |
n.a. |
n.a. |
PMID[23999046] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[24479468] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
roots |
n.a. |
n.a. |
PMID[24957203] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[25445757] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[25744461] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[26841168] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
Leaves |
n.a. |
n.a. |
PMID[28453270] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[32196343] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
root |
n.a. |
PMID[9397205] |
NPO17171 |
Tripterospermum taiwanense |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[Article] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
Flower |
n.a. |
n.a. |
Database[FooDB] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
Fruit |
n.a. |
n.a. |
Database[FooDB] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
Leaf |
n.a. |
n.a. |
Database[FooDB] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
Leaf |
n.a. |
n.a. |
Database[FooDB] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
Plant |
n.a. |
n.a. |
Database[FooDB] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
Plant |
n.a. |
n.a. |
Database[FooDB] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
Root |
n.a. |
n.a. |
Database[FooDB] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
Seed |
n.a. |
n.a. |
Database[FooDB] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
Stem |
n.a. |
n.a. |
Database[FooDB] |
NPO27288 |
Citrus maxima |
Species |
Rutaceae |
Eukaryota |
|
n.a. |
n.a. |
Database[FooDB] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
|
n.a. |
n.a. |
Database[FooDB] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
|
n.a. |
n.a. |
Database[FooDB] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
|
Database[FooDB] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO17171 |
Tripterospermum taiwanense |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO27288 |
Citrus maxima |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
|
Database[Phenol-Explorer] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
n.a. |
n.a. |
|
Database[Phenol-Explorer] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
|
Database[Phenol-Explorer] |
NPO27288 |
Citrus maxima |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO17171 |
Tripterospermum taiwanense |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO23984 |
Metagentiana rhodantha |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO27288 |
Citrus maxima |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO23984 |
Metagentiana rhodantha |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO27288 |
Citrus maxima |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO21373 |
Vitex trifolia |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO17171 |
Tripterospermum taiwanense |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO8210 |
Trigonella foenum-graecum |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO22686 |
Gentiana macrophylla |
Species |
Gentianaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO7154 |
Glycyrrhiza uralensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO12011 |
Crataegus pinnatifida |
Species |
Rosaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO2838 |
Verbena officinalis |
Species |
Verbenaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].
  NP Quantity Composition/Concentration
Organism ID |
NP ID |
Organism Material Preparation |
Organism Part |
NP Quantity (Standard) |
NP Quantity (Minimum) |
NP Quantity (Maximum) |
Quantity Unit |
Reference |
☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].
  Biological Activity
Target ID |
Target Type |
Target Name |
Target Organism |
Activity Type |
Activity Relation |
Value |
Unit |
Reference |
☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.
  Chemically structural similarity: I. Similar Active Natural Products in NPASS
Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)
Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
●  The left chart: Distribution of similarity level between NPC53558 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).
range |
Tanimoto Coefficient |
0-0.1 | 463 |
0.1-0.2 | 1771 |
0.2-0.3 | 4048 |
0.3-0.4 | 9995 |
0.4-0.5 | 8229 |
0.5-0.6 | 3820 |
0.6-0.7 | 4990 |
0.7-0.8 | 4870 |
0.8-0.85 | 2295 |
0.85-0.9 | 1745 |
0.9-0.95 | 453 |
0.95-1 | 18 |
Similarity Score |
Similarity Level |
Natural Product ID |
  Chemically structural similarity: II. Similar Clinical/Approved Drugs
Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.
●  The left chart: Distribution of similarity level between NPC53558 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).
range |
Tanimoto Coefficient |
0-0.1 | 419 |
0.1-0.2 | 908 |
0.2-0.3 | 1824 |
0.3-0.4 | 2652 |
0.4-0.5 | 1837 |
0.5-0.6 | 960 |
0.6-0.7 | 369 |
0.7-0.8 | 126 |
0.8-0.85 | 23 |
0.85-0.9 | 24 |
0.9-0.95 | 8 |
0.95-1 | 0 |
Similarity Score |
Similarity Level |
Drug ID |
Developmental Stage |