Structure

Physi-Chem Properties

Molecular Weight:  167.09
Volume:  176.332
LogP:  -0.223
LogD:  0.174
LogS:  -1.928
# Rotatable Bonds:  3
TPSA:  52.49
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.619
Synthetic Accessibility Score:  2.4
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.979
MDCK Permeability:  7.869082764955238e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.698
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.21
Plasma Protein Binding (PPB):  19.40147590637207%
Volume Distribution (VD):  2.411
Pgp-substrate:  82.53878021240234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.219
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.535
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.776
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.728
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.139

ADMET: Excretion

Clearance (CL):  10.427
Half-life (T1/2):  0.756

ADMET: Toxicity

hERG Blockers:  0.075
Human Hepatotoxicity (H-HT):  0.158
Drug-inuced Liver Injury (DILI):  0.015
AMES Toxicity:  0.032
Rat Oral Acute Toxicity:  0.642
Maximum Recommended Daily Dose:  0.892
Skin Sensitization:  0.816
Carcinogencity:  0.038
Eye Corrosion:  0.005
Eye Irritation:  0.039
Respiratory Toxicity:  0.664

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC213

Natural Product ID:  NPC213
Common Name*:   Oxedrine
IUPAC Name:   4-[1-hydroxy-2-(methylamino)ethyl]phenol
Synonyms:   Oxedrine; Synephrine
Standard InCHIKey:  YRCWQPVGYLYSOX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
SMILES:  CNCC(c1ccc(cc1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL33720
PubChem CID:   7172
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. stem n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15577255]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17689080]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[21465337]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[23872723]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30188125]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[32996318]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO4877 Euodia officinalis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16845 Euodia bodinieri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10082 Citrus unshiu Species Rutaceae 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
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 3548.1 nM PMID[515314]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 17782.8 nM PMID[515315]
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 2.8 nM PMID[515313]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 22.4 nM PMID[515313]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 70794.6 nM PMID[515315]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 11220.2 nM PMID[515319]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 3981.1 nM PMID[515319]
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency n.a. 42163.2 nM PMID[515314]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 2660.3 nM PMID[515314]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 1778.3 nM PMID[515319]
NPT104 Individual Protein Cerebroside-sulfatase Homo sapiens Potency n.a. 2685.5 nM PMID[515317]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 100000.0 nM PMID[515315]
NPT107 Individual Protein Neuromedin-U receptor 2 Homo sapiens EC50 = 6600.0 nM PMID[515323]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 1094.7 nM PubChem BioAssay data set
NPT2 Others Unspecified -Log KD = -1.58 n.a. PMID[515310]
NPT92 Individual Protein Serotonin 1a (5-HT1a) receptor Homo sapiens Ki = 63000.0 nM PMID[515311]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 707.9 nM PMID[515313]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 22387.2 nM PMID[515314]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Potency = 1412.5 nM PMID[515314]
NPT96 Individual Protein Thrombopoietin Homo sapiens Potency = 10000.0 nM PMID[515314]
NPT2 Others Unspecified Potency = 3162.3 nM PMID[515314]
NPT2 Others Unspecified Potency = 2818.4 nM PMID[515313]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 18887.6 nM PMID[515317]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 18887.6 nM PMID[515318]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 79432.8 nM PMID[515319]
NPT98 Individual Protein HERG Homo sapiens Potency n.a. 22387.2 nM PMID[515313]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 31622.8 nM PMID[515314]
NPT2 Others Unspecified Potency n.a. 316.2 nM PMID[515313]
NPT35 Others n.a. pKa n.a. 9.6 n.a. PMID[515320]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 23694.5 nM PMID[515321]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 1.1 nM PMID[515321]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 5304.5 nM PMID[515321]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 749.3 nM PMID[515321]
NPT2 Others Unspecified Potency n.a. 1589.1 nM PMID[515322]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[515319]
NPT2 Others Unspecified AC50 n.a. 11220.2 nM PMID[515324]
NPT2 Others Unspecified Ac50 n.a. 2.818 uM PMID[515324]
NPT2 Others Unspecified Ac50 n.a. 11.22 uM PMID[515324]
NPT2 Others Unspecified Ac50 n.a. 7.943 uM PMID[515324]
NPT2 Others Unspecified AC50 n.a. 2818.4 nM PMID[515324]
NPT2 Others Unspecified AC50 n.a. 7943.3 nM PMID[515324]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 1000000.0 nM PMID[515325]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = 0.9175 n.a. PMID[515326]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 24.21 % PMID[515327]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.07332 n.a. PMID[515328]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 19.66 % PMID[515329]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.01 % PMID[515330]
NPT20 Organism Candida albicans Candida albicans Inhibition = 5.72 % PMID[515331]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = 1.4 % PMID[515331]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 6.6 % PMID[515331]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = -0.12 % PMID[515331]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 6.75 % PMID[515331]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 11.3 % PMID[515331]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = -16.09 % PMID[515331]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[515332]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[515332]
NPT2 Others Unspecified Potency n.a. 61561.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19467.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68450.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15463.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4522 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set

☑ 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 NPC213 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC10286
0.9439 High Similarity NPC290566
0.9439 High Similarity NPC145638
0.9115 High Similarity NPC137096
0.8992 High Similarity NPC236347
0.8992 High Similarity NPC323775
0.8785 High Similarity NPC327226
0.8624 High Similarity NPC147000
0.8624 High Similarity NPC150254
0.8624 High Similarity NPC226778
0.8624 High Similarity NPC304761
0.8598 High Similarity NPC125732
0.8559 High Similarity NPC115627
0.8559 High Similarity NPC118522
0.8559 High Similarity NPC169207
0.8525 High Similarity NPC322366
0.8519 High Similarity NPC155847
0.8519 High Similarity NPC289381
0.843 Intermediate Similarity NPC307020
0.839 Intermediate Similarity NPC85276
0.8318 Intermediate Similarity NPC313650
0.8224 Intermediate Similarity NPC215351
0.8224 Intermediate Similarity NPC20142
0.8198 Intermediate Similarity NPC178902
0.8198 Intermediate Similarity NPC68055
0.8189 Intermediate Similarity NPC208757
0.8165 Intermediate Similarity NPC303611
0.8165 Intermediate Similarity NPC290515
0.8165 Intermediate Similarity NPC164514
0.8165 Intermediate Similarity NPC108606
0.8165 Intermediate Similarity NPC226096
0.8131 Intermediate Similarity NPC138117
0.8131 Intermediate Similarity NPC325292
0.8034 Intermediate Similarity NPC146422
0.8018 Intermediate Similarity NPC214200
0.8018 Intermediate Similarity NPC29601
0.8018 Intermediate Similarity NPC228400
0.8017 Intermediate Similarity NPC283760
0.7982 Intermediate Similarity NPC231705
0.7969 Intermediate Similarity NPC329595
0.7969 Intermediate Similarity NPC326599
0.7944 Intermediate Similarity NPC300478
0.7944 Intermediate Similarity NPC300017
0.7931 Intermediate Similarity NPC258056
0.7917 Intermediate Similarity NPC188867
0.7917 Intermediate Similarity NPC281686
0.7917 Intermediate Similarity NPC106551
0.7913 Intermediate Similarity NPC142297
0.7863 Intermediate Similarity NPC474149
0.7857 Intermediate Similarity NPC320242
0.7845 Intermediate Similarity NPC153690
0.7838 Intermediate Similarity NPC107619
0.7778 Intermediate Similarity NPC95733
0.7778 Intermediate Similarity NPC62101
0.7761 Intermediate Similarity NPC168861
0.7757 Intermediate Similarity NPC104216
0.775 Intermediate Similarity NPC118202
0.7739 Intermediate Similarity NPC42383
0.7724 Intermediate Similarity NPC239697
0.7717 Intermediate Similarity NPC29477
0.7692 Intermediate Similarity NPC97811
0.7692 Intermediate Similarity NPC96224
0.7692 Intermediate Similarity NPC24101
0.7686 Intermediate Similarity NPC317254
0.768 Intermediate Similarity NPC474862
0.7667 Intermediate Similarity NPC59387
0.7664 Intermediate Similarity NPC23167
0.7634 Intermediate Similarity NPC247018
0.7634 Intermediate Similarity NPC97870
0.7634 Intermediate Similarity NPC307123
0.7612 Intermediate Similarity NPC214988
0.7611 Intermediate Similarity NPC51333
0.7611 Intermediate Similarity NPC132078
0.7611 Intermediate Similarity NPC128723
0.7611 Intermediate Similarity NPC78119
0.7611 Intermediate Similarity NPC216468
0.7603 Intermediate Similarity NPC142599
0.7594 Intermediate Similarity NPC64205
0.7593 Intermediate Similarity NPC113460
0.7593 Intermediate Similarity NPC25493
0.7578 Intermediate Similarity NPC136112
0.7578 Intermediate Similarity NPC318965
0.7578 Intermediate Similarity NPC141739
0.7574 Intermediate Similarity NPC204546
0.757 Intermediate Similarity NPC197783
0.7559 Intermediate Similarity NPC13020
0.7559 Intermediate Similarity NPC140359
0.7559 Intermediate Similarity NPC211218
0.7544 Intermediate Similarity NPC213730
0.754 Intermediate Similarity NPC27581
0.7523 Intermediate Similarity NPC123273
0.7523 Intermediate Similarity NPC258219
0.7523 Intermediate Similarity NPC177420
0.7523 Intermediate Similarity NPC280347
0.7523 Intermediate Similarity NPC318325
0.7523 Intermediate Similarity NPC242240
0.7522 Intermediate Similarity NPC474073
0.7521 Intermediate Similarity NPC26524
0.75 Intermediate Similarity NPC142638
0.75 Intermediate Similarity NPC317784
0.75 Intermediate Similarity NPC12278
0.748 Intermediate Similarity NPC82963
0.748 Intermediate Similarity NPC298486
0.7479 Intermediate Similarity NPC24777
0.7478 Intermediate Similarity NPC7686
0.7478 Intermediate Similarity NPC40258
0.7478 Intermediate Similarity NPC91461
0.7477 Intermediate Similarity NPC175313
0.7477 Intermediate Similarity NPC248817
0.746 Intermediate Similarity NPC56634
0.7458 Intermediate Similarity NPC251306
0.7458 Intermediate Similarity NPC186469
0.7456 Intermediate Similarity NPC80027
0.7455 Intermediate Similarity NPC55561
0.7444 Intermediate Similarity NPC267237
0.744 Intermediate Similarity NPC319950
0.7436 Intermediate Similarity NPC233396
0.7436 Intermediate Similarity NPC154899
0.7436 Intermediate Similarity NPC471350
0.7422 Intermediate Similarity NPC328267
0.7422 Intermediate Similarity NPC318777
0.7419 Intermediate Similarity NPC311737
0.7419 Intermediate Similarity NPC38458
0.7414 Intermediate Similarity NPC305205
0.7391 Intermediate Similarity NPC130103
0.7387 Intermediate Similarity NPC45040
0.7387 Intermediate Similarity NPC304541
0.7383 Intermediate Similarity NPC124436
0.7383 Intermediate Similarity NPC265146
0.7381 Intermediate Similarity NPC321133
0.7373 Intermediate Similarity NPC135464
0.7373 Intermediate Similarity NPC92623
0.7372 Intermediate Similarity NPC469360
0.7368 Intermediate Similarity NPC33338
0.7368 Intermediate Similarity NPC302171
0.7368 Intermediate Similarity NPC300020
0.7364 Intermediate Similarity NPC171372
0.7348 Intermediate Similarity NPC474087
0.7345 Intermediate Similarity NPC26244
0.7339 Intermediate Similarity NPC407
0.7339 Intermediate Similarity NPC184169
0.7339 Intermediate Similarity NPC307235
0.7329 Intermediate Similarity NPC37205
0.7329 Intermediate Similarity NPC160931
0.7328 Intermediate Similarity NPC471578
0.7328 Intermediate Similarity NPC110764
0.7328 Intermediate Similarity NPC101025
0.7323 Intermediate Similarity NPC318357
0.7323 Intermediate Similarity NPC284078
0.7323 Intermediate Similarity NPC326079
0.7317 Intermediate Similarity NPC115803
0.7311 Intermediate Similarity NPC61033
0.7311 Intermediate Similarity NPC305603
0.7304 Intermediate Similarity NPC100870
0.7302 Intermediate Similarity NPC43275
0.7299 Intermediate Similarity NPC197921
0.7297 Intermediate Similarity NPC47950
0.7297 Intermediate Similarity NPC312304
0.7293 Intermediate Similarity NPC326966
0.7281 Intermediate Similarity NPC473388
0.728 Intermediate Similarity NPC120075
0.7279 Intermediate Similarity NPC473055
0.7279 Intermediate Similarity NPC473052
0.7273 Intermediate Similarity NPC475018
0.7273 Intermediate Similarity NPC27974
0.7273 Intermediate Similarity NPC271808
0.7273 Intermediate Similarity NPC325651
0.7266 Intermediate Similarity NPC142577
0.7259 Intermediate Similarity NPC470441
0.7257 Intermediate Similarity NPC151715
0.7257 Intermediate Similarity NPC27323
0.7257 Intermediate Similarity NPC316301
0.7257 Intermediate Similarity NPC128062
0.725 Intermediate Similarity NPC317305
0.7248 Intermediate Similarity NPC155393
0.7246 Intermediate Similarity NPC91953
0.7246 Intermediate Similarity NPC251439
0.7241 Intermediate Similarity NPC294741
0.7241 Intermediate Similarity NPC174911
0.7239 Intermediate Similarity NPC88667
0.7239 Intermediate Similarity NPC149379
0.7232 Intermediate Similarity NPC155908
0.7232 Intermediate Similarity NPC270547
0.7232 Intermediate Similarity NPC204210
0.7226 Intermediate Similarity NPC41473
0.7226 Intermediate Similarity NPC48202
0.7226 Intermediate Similarity NPC204848
0.7226 Intermediate Similarity NPC322526
0.7226 Intermediate Similarity NPC312770
0.7226 Intermediate Similarity NPC14600
0.7226 Intermediate Similarity NPC160607
0.7218 Intermediate Similarity NPC262641
0.7217 Intermediate Similarity NPC260000
0.7213 Intermediate Similarity NPC21890
0.7207 Intermediate Similarity NPC98772
0.7197 Intermediate Similarity NPC145888
0.7197 Intermediate Similarity NPC16031
0.7197 Intermediate Similarity NPC161593
0.7194 Intermediate Similarity NPC326241
0.7193 Intermediate Similarity NPC8392

  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 NPC213 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9817 High Similarity NPD318 Approved
0.9817 High Similarity NPD856 Approved
0.9817 High Similarity NPD317 Approved
0.9817 High Similarity NPD16 Approved
0.9439 High Similarity NPD9380 Clinical (unspecified phase)
0.9304 High Similarity NPD2561 Approved
0.9304 High Similarity NPD2562 Approved
0.9115 High Similarity NPD9615 Approved
0.9115 High Similarity NPD9613 Approved
0.9115 High Similarity NPD9616 Approved
0.9068 High Similarity NPD1133 Approved
0.9068 High Similarity NPD1135 Approved
0.9068 High Similarity NPD1131 Approved
0.9068 High Similarity NPD1129 Approved
0.9068 High Similarity NPD1134 Approved
0.9035 High Similarity NPD316 Approved
0.8992 High Similarity NPD9620 Approved
0.8992 High Similarity NPD9619 Approved
0.8992 High Similarity NPD9621 Approved
0.8699 High Similarity NPD601 Approved
0.8699 High Similarity NPD598 Approved
0.8699 High Similarity NPD597 Approved
0.8629 High Similarity NPD1132 Approved
0.8629 High Similarity NPD1136 Approved
0.8629 High Similarity NPD829 Discontinued
0.8629 High Similarity NPD1130 Approved
0.8624 High Similarity NPD9610 Approved
0.8624 High Similarity NPD309 Approved
0.8624 High Similarity NPD314 Approved
0.8624 High Similarity NPD315 Approved
0.8624 High Similarity NPD311 Approved
0.8624 High Similarity NPD10 Approved
0.8624 High Similarity NPD310 Approved
0.8624 High Similarity NPD9608 Approved
0.8559 High Similarity NPD9384 Approved
0.8559 High Similarity NPD9381 Approved
0.8525 High Similarity NPD602 Approved
0.8525 High Similarity NPD599 Approved
0.8525 High Similarity NPD859 Approved
0.8525 High Similarity NPD858 Approved
0.8522 High Similarity NPD9618 Approved
0.8522 High Similarity NPD9614 Approved
0.848 Intermediate Similarity NPD6405 Approved
0.848 Intermediate Similarity NPD6407 Approved
0.843 Intermediate Similarity NPD4659 Approved
0.843 Intermediate Similarity NPD9622 Approved
0.8425 Intermediate Similarity NPD2568 Approved
0.8425 Intermediate Similarity NPD3054 Approved
0.8425 Intermediate Similarity NPD3052 Approved
0.8413 Intermediate Similarity NPD3062 Approved
0.8413 Intermediate Similarity NPD3059 Approved
0.8413 Intermediate Similarity NPD3061 Approved
0.8359 Intermediate Similarity NPD3554 Approved
0.8359 Intermediate Similarity NPD3552 Approved
0.8359 Intermediate Similarity NPD3553 Approved
0.8359 Intermediate Similarity NPD3555 Approved
0.8293 Intermediate Similarity NPD4103 Phase 2
0.8293 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.8281 Intermediate Similarity NPD817 Approved
0.8281 Intermediate Similarity NPD823 Approved
0.8281 Intermediate Similarity NPD5314 Approved
0.825 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.8165 Intermediate Similarity NPD9611 Approved
0.8165 Intermediate Similarity NPD9612 Approved
0.8165 Intermediate Similarity NPD9609 Approved
0.8045 Intermediate Similarity NPD3060 Approved
0.8034 Intermediate Similarity NPD9377 Approved
0.8034 Intermediate Similarity NPD9379 Approved
0.7969 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD2229 Approved
0.7966 Intermediate Similarity NPD2228 Approved
0.7966 Intermediate Similarity NPD2234 Approved
0.7946 Intermediate Similarity NPD854 Approved
0.7946 Intermediate Similarity NPD855 Approved
0.792 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD9568 Approved
0.7857 Intermediate Similarity NPD3053 Approved
0.7857 Intermediate Similarity NPD1819 Approved
0.7857 Intermediate Similarity NPD1818 Approved
0.7857 Intermediate Similarity NPD3055 Approved
0.7857 Intermediate Similarity NPD1820 Approved
0.7857 Intermediate Similarity NPD1817 Approved
0.7826 Intermediate Similarity NPD1444 Approved
0.7826 Intermediate Similarity NPD1445 Approved
0.7778 Intermediate Similarity NPD5311 Approved
0.7778 Intermediate Similarity NPD5310 Approved
0.7754 Intermediate Similarity NPD3536 Discontinued
0.7752 Intermediate Similarity NPD3136 Phase 2
0.7752 Intermediate Similarity NPD3180 Approved
0.7752 Intermediate Similarity NPD3179 Approved
0.7742 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD828 Approved
0.7686 Intermediate Similarity NPD255 Approved
0.7686 Intermediate Similarity NPD256 Approved
0.7647 Intermediate Similarity NPD3638 Discontinued
0.7642 Intermediate Similarity NPD2227 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD1423 Approved
0.7627 Intermediate Similarity NPD1792 Phase 2
0.7615 Intermediate Similarity NPD3164 Approved
0.7615 Intermediate Similarity NPD3167 Approved
0.7615 Intermediate Similarity NPD3165 Approved
0.7615 Intermediate Similarity NPD3166 Approved
0.7603 Intermediate Similarity NPD593 Approved
0.7603 Intermediate Similarity NPD595 Approved
0.7581 Intermediate Similarity NPD1710 Approved
0.7578 Intermediate Similarity NPD1794 Approved
0.754 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD7451 Discontinued
0.7518 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD551 Approved
0.7479 Intermediate Similarity NPD550 Approved
0.7465 Intermediate Similarity NPD3687 Approved
0.7465 Intermediate Similarity NPD3686 Approved
0.7459 Intermediate Similarity NPD1793 Approved
0.7459 Intermediate Similarity NPD1791 Approved
0.744 Intermediate Similarity NPD4093 Discontinued
0.7426 Intermediate Similarity NPD9570 Approved
0.7426 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD2428 Approved
0.7422 Intermediate Similarity NPD2429 Approved
0.7413 Intermediate Similarity NPD6056 Approved
0.7413 Intermediate Similarity NPD6057 Approved
0.7411 Intermediate Similarity NPD2933 Approved
0.7411 Intermediate Similarity NPD2934 Approved
0.7405 Intermediate Similarity NPD600 Approved
0.7405 Intermediate Similarity NPD596 Approved
0.7391 Intermediate Similarity NPD4162 Approved
0.7383 Intermediate Similarity NPD111 Approved
0.7381 Intermediate Similarity NPD2668 Approved
0.7381 Intermediate Similarity NPD2556 Approved
0.7381 Intermediate Similarity NPD2554 Approved
0.7381 Intermediate Similarity NPD2667 Approved
0.7372 Intermediate Similarity NPD7978 Discontinued
0.736 Intermediate Similarity NPD5303 Approved
0.736 Intermediate Similarity NPD5304 Approved
0.7345 Intermediate Similarity NPD2859 Approved
0.7345 Intermediate Similarity NPD2860 Approved
0.7344 Intermediate Similarity NPD2231 Phase 2
0.7344 Intermediate Similarity NPD4273 Approved
0.7344 Intermediate Similarity NPD2235 Phase 2
0.7329 Intermediate Similarity NPD2977 Approved
0.7329 Intermediate Similarity NPD2978 Approved
0.7328 Intermediate Similarity NPD940 Approved
0.7328 Intermediate Similarity NPD846 Approved
0.7323 Intermediate Similarity NPD3421 Phase 3
0.7302 Intermediate Similarity NPD770 Discontinued
0.7287 Intermediate Similarity NPD6583 Phase 3
0.7287 Intermediate Similarity NPD6582 Phase 2
0.7286 Intermediate Similarity NPD8131 Suspended
0.7279 Intermediate Similarity NPD3558 Approved
0.7279 Intermediate Similarity NPD3556 Approved
0.7279 Intermediate Similarity NPD3560 Approved
0.7279 Intermediate Similarity NPD3559 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD3557 Approved
0.7259 Intermediate Similarity NPD555 Phase 2
0.7257 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD3158 Phase 1
0.7254 Intermediate Similarity NPD3645 Discontinued
0.7254 Intermediate Similarity NPD3157 Approved
0.7252 Intermediate Similarity NPD558 Phase 2
0.7246 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD1751 Approved
0.7239 Intermediate Similarity NPD3163 Approved
0.7239 Intermediate Similarity NPD839 Approved
0.7239 Intermediate Similarity NPD3162 Approved
0.7239 Intermediate Similarity NPD840 Approved
0.7239 Intermediate Similarity NPD259 Phase 1
0.7231 Intermediate Similarity NPD196 Phase 1
0.7226 Intermediate Similarity NPD1753 Discontinued
0.7222 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD5163 Phase 2
0.7218 Intermediate Similarity NPD6179 Discontinued
0.7211 Intermediate Similarity NPD6283 Phase 2
0.7197 Intermediate Similarity NPD9569 Approved
0.7185 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD2238 Phase 2
0.7174 Intermediate Similarity NPD2240 Approved
0.7174 Intermediate Similarity NPD2239 Approved
0.7167 Intermediate Similarity NPD4095 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD3049 Approved
0.7163 Intermediate Similarity NPD2677 Approved
0.7155 Intermediate Similarity NPD3020 Approved
0.7143 Intermediate Similarity NPD2459 Approved
0.7143 Intermediate Similarity NPD2458 Approved
0.7143 Intermediate Similarity NPD2460 Phase 3
0.7133 Intermediate Similarity NPD5709 Phase 3
0.7122 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD6584 Phase 3
0.7121 Intermediate Similarity NPD2194 Approved
0.7121 Intermediate Similarity NPD2195 Approved
0.7113 Intermediate Similarity NPD3122 Phase 3
0.7111 Intermediate Similarity NPD3532 Approved
0.7111 Intermediate Similarity NPD3530 Approved
0.7111 Intermediate Similarity NPD3531 Approved
0.7092 Intermediate Similarity NPD7066 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4666 Phase 3
0.7083 Intermediate Similarity NPD2559 Approved
0.7083 Intermediate Similarity NPD2551 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data