Structure

Physi-Chem Properties

Molecular Weight:  129.04
Volume:  118.574
LogP:  -0.692
LogD:  -0.137
LogS:  -0.802
# Rotatable Bonds:  1
TPSA:  76.48
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.393
Synthetic Accessibility Score:  3.726
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.198
MDCK Permeability:  0.0028497816529124975
Pgp-inhibitor:  0.001
Pgp-substrate:  0.022
Human Intestinal Absorption (HIA):  0.029
20% Bioavailability (F20%):  0.868
30% Bioavailability (F30%):  0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.248
Plasma Protein Binding (PPB):  15.069440841674805%
Volume Distribution (VD):  1.642
Pgp-substrate:  76.89891815185547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.1
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.545
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.431
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.041

ADMET: Excretion

Clearance (CL):  3.657
Half-life (T1/2):  0.852

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.152
Drug-inuced Liver Injury (DILI):  0.116
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.019
Maximum Recommended Daily Dose:  0.054
Skin Sensitization:  0.139
Carcinogencity:  0.576
Eye Corrosion:  0.003
Eye Irritation:  0.958
Respiratory Toxicity:  0.765

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC19576

Natural Product ID:  NPC19576
Common Name*:   Pyroglutamic Acid
IUPAC Name:   (2S)-5-oxopyrrolidine-2-carboxylic acid
Synonyms:   Pidolic Acid
Standard InCHIKey:  ODHCTXKNWHHXJC-VKHMYHEASA-N
Standard InCHI:  InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
SMILES:  OC(=O)[C@@H]1CCC(=N1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL397976
PubChem CID:   7405
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota Flowers Tantempango, Hidalgo, Mexico 2019-May DOI[10.1007/s11130-020-00822-2]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. Wrocław, Poland 2004–2005 DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/jf950732o]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10775096]
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]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. bulb n.a. PMID[14994197]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15577255]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[15844951]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. root n.a. PMID[1622242]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. PMID[16297615]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16659156]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16668466]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota tubers n.a. n.a. PMID[16792409]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. whole plant n.a. PMID[18543151]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. PMID[20581114]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[20963508]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[23627123]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. PMID[24358188]
NPO7635 Glycine max Species Fabaceae Eukaryota Seeds Tekirdag, Turkey PMID[24499198]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25053043]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25070365]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. seed n.a. PMID[25369450]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25369450]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. PMID[25515814]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30188125]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO41565 Trichoderma asperellum GDFS1009 + Bacillus amyloliquefaciens 1841(TB2) Strain n.a. n.a. n.a. n.a. n.a. PMID[31665025]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[32004936]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. PMID[8778246]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO7635 Glycine max Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Testa n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Hypocotyl n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. seed n.a. Database[MetaboLights]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO7635 Glycine max Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae 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]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2837 Aloe spicata Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2997 Aloe africana Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2997 Aloe africana Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1756 Cremastra appendiculata Species Orchidaceae 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
NPO7635 NPC19576 Raw Seed 200 100 300 mg/100g Database [DUKE]

☑ 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
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 5.6 nM PMID[479797]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 35481.3 nM PMID[479798]
NPT445 Individual Protein Peripheral myelin protein 22 Rattus norvegicus Potency n.a. 405.3 nM PMID[479797]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16.4 nM PMID[479798]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 5309.1 nM PMID[479799]
NPT2 Others Unspecified Inhibition = 67.0 % PMID[479796]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 0.69 n.a. PMID[479796]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 0.75 n.a. PMID[479796]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13459.1 nM PMID[479797]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 19011.5 nM PMID[479797]
NPT474 Organism Plasmodium berghei Plasmodium berghei Survival = 0.0 % PMID[479800]
NPT2 Others Unspecified Ac50 n.a. 3.981 uM PMID[479801]
NPT2 Others Unspecified Ac50 n.a. 2.239 uM PMID[479801]
NPT2 Others Unspecified AC50 n.a. 3981.1 nM PMID[479801]
NPT2 Others Unspecified AC50 n.a. 2238.7 nM PMID[479801]
NPT825 Organism Phytophthora infestans Phytophthora infestans Inhibition = 98.85 % PMID[479802]
NPT825 Organism Phytophthora infestans Phytophthora infestans EC50 = 7.85 ug.mL-1 PMID[479802]
NPT1261 Organism Bacillus thuringiensis Bacillus thuringiensis IZ = 17.5 mm PMID[479802]
NPT331 Organism Ralstonia solanacearum Ralstonia solanacearum IZ = 7.5 mm PMID[479802]
NPT825 Organism Phytophthora infestans Phytophthora infestans EC50 = 9.48 ug.mL-1 PMID[479802]
NPT5415 Organism Pseudoperonospora cubensis Pseudoperonospora cubensis EC50 = 10.82 ug.mL-1 PMID[479802]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.1555 n.a. PMID[479803]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 18.63 % PMID[479804]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.06 % PMID[479805]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[479806]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[479806]
NPT2 Others Unspecified Potency n.a. 12.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 84.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2391.4 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 NPC19576 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 NPC29950
0.86 High Similarity NPC327239
0.8302 Intermediate Similarity NPC322573
0.8269 Intermediate Similarity NPC189178
0.8269 Intermediate Similarity NPC263065
0.8148 Intermediate Similarity NPC325985
0.8148 Intermediate Similarity NPC38463
0.7925 Intermediate Similarity NPC190184
0.7925 Intermediate Similarity NPC197087
0.7719 Intermediate Similarity NPC321536
0.7586 Intermediate Similarity NPC143722
0.7407 Intermediate Similarity NPC322946
0.7333 Intermediate Similarity NPC327252
0.7213 Intermediate Similarity NPC289691
0.7143 Intermediate Similarity NPC118524
0.7097 Intermediate Similarity NPC325597
0.7097 Intermediate Similarity NPC174304
0.6909 Remote Similarity NPC137958
0.6909 Remote Similarity NPC273330
0.6833 Remote Similarity NPC254541
0.6833 Remote Similarity NPC321468
0.6833 Remote Similarity NPC316826
0.6833 Remote Similarity NPC327748
0.6833 Remote Similarity NPC320598
0.6833 Remote Similarity NPC317143
0.678 Remote Similarity NPC317147
0.678 Remote Similarity NPC318260
0.6769 Remote Similarity NPC319046
0.6721 Remote Similarity NPC327170
0.6721 Remote Similarity NPC329564
0.6667 Remote Similarity NPC189301
0.6667 Remote Similarity NPC126779
0.6667 Remote Similarity NPC176164
0.6604 Remote Similarity NPC327698
0.6604 Remote Similarity NPC118459
0.66 Remote Similarity NPC33721
0.6545 Remote Similarity NPC227850
0.6481 Remote Similarity NPC297220
0.6441 Remote Similarity NPC2801
0.6429 Remote Similarity NPC328378
0.6383 Remote Similarity NPC145895
0.6349 Remote Similarity NPC477644
0.6275 Remote Similarity NPC327250
0.6271 Remote Similarity NPC321118
0.6271 Remote Similarity NPC316889
0.625 Remote Similarity NPC93081
0.625 Remote Similarity NPC153370
0.625 Remote Similarity NPC59867
0.625 Remote Similarity NPC140872
0.6182 Remote Similarity NPC306238
0.6182 Remote Similarity NPC248970
0.6167 Remote Similarity NPC327831
0.6164 Remote Similarity NPC314680
0.6154 Remote Similarity NPC57420
0.6154 Remote Similarity NPC145658
0.614 Remote Similarity NPC84636
0.614 Remote Similarity NPC21142
0.614 Remote Similarity NPC162620
0.614 Remote Similarity NPC112890
0.614 Remote Similarity NPC226027
0.614 Remote Similarity NPC43204
0.614 Remote Similarity NPC316231
0.614 Remote Similarity NPC174246
0.614 Remote Similarity NPC245027
0.614 Remote Similarity NPC324825
0.614 Remote Similarity NPC62045
0.6042 Remote Similarity NPC260324
0.6034 Remote Similarity NPC319110
0.6034 Remote Similarity NPC329181
0.6032 Remote Similarity NPC473599
0.6 Remote Similarity NPC329263
0.597 Remote Similarity NPC325534
0.5938 Remote Similarity NPC68974
0.5921 Remote Similarity NPC475542
0.5873 Remote Similarity NPC245346
0.5873 Remote Similarity NPC11433
0.5873 Remote Similarity NPC302003
0.5857 Remote Similarity NPC477642
0.5849 Remote Similarity NPC168375
0.5849 Remote Similarity NPC121517
0.5849 Remote Similarity NPC326992
0.5833 Remote Similarity NPC329495
0.5806 Remote Similarity NPC313263
0.5775 Remote Similarity NPC328457
0.5763 Remote Similarity NPC319175
0.5738 Remote Similarity NPC183845
0.5738 Remote Similarity NPC279661
0.5735 Remote Similarity NPC470108
0.5732 Remote Similarity NPC193386
0.5714 Remote Similarity NPC278209
0.5694 Remote Similarity NPC315897
0.5694 Remote Similarity NPC320865
0.5694 Remote Similarity NPC477641
0.5694 Remote Similarity NPC477643
0.5692 Remote Similarity NPC321419
0.5672 Remote Similarity NPC88898
0.5672 Remote Similarity NPC106216
0.5667 Remote Similarity NPC200550
0.5667 Remote Similarity NPC155156
0.5652 Remote Similarity NPC470109
0.5636 Remote Similarity NPC291186
0.5636 Remote Similarity NPC167986
0.5636 Remote Similarity NPC276294
0.5634 Remote Similarity NPC478256
0.5606 Remote Similarity NPC118429

  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 NPC19576 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
1.0 High Similarity NPD61 Approved
1.0 High Similarity NPD8846 Approved
1.0 High Similarity NPD8847 Approved
0.8269 Intermediate Similarity NPD9205 Approved
0.8269 Intermediate Similarity NPD9204 Approved
0.7925 Intermediate Similarity NPD8785 Approved
0.7857 Intermediate Similarity NPD9433 Approved
0.7458 Intermediate Similarity NPD574 Approved
0.7407 Intermediate Similarity NPD9441 Phase 2
0.7333 Intermediate Similarity NPD575 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD348 Approved
0.6909 Remote Similarity NPD8872 Phase 3
0.6909 Remote Similarity NPD8871 Approved
0.6875 Remote Similarity NPD886 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1429 Clinical (unspecified phase)
0.6769 Remote Similarity NPD337 Discontinued
0.6769 Remote Similarity NPD4241 Registered
0.6667 Remote Similarity NPD4242 Approved
0.6667 Remote Similarity NPD8851 Phase 1
0.66 Remote Similarity NPD8576 Approved
0.6552 Remote Similarity NPD9419 Clinical (unspecified phase)
0.6471 Remote Similarity NPD2262 Clinical (unspecified phase)
0.6377 Remote Similarity NPD6944 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8842 Clinical (unspecified phase)
0.6296 Remote Similarity NPD9658 Clinical (unspecified phase)
0.6269 Remote Similarity NPD322 Phase 1
0.6267 Remote Similarity NPD1448 Clinical (unspecified phase)
0.625 Remote Similarity NPD8809 Approved
0.625 Remote Similarity NPD8808 Approved
0.625 Remote Similarity NPD8577 Discontinued
0.625 Remote Similarity NPD8614 Approved
0.6182 Remote Similarity NPD8870 Approved
0.6143 Remote Similarity NPD1147 Phase 2
0.614 Remote Similarity NPD9200 Approved
0.614 Remote Similarity NPD9016 Clinical (unspecified phase)
0.614 Remote Similarity NPD9018 Approved
0.614 Remote Similarity NPD9044 Approved
0.614 Remote Similarity NPD9017 Approved
0.597 Remote Similarity NPD8952 Approved
0.5965 Remote Similarity NPD9214 Phase 3
0.5965 Remote Similarity NPD9213 Approved
0.5946 Remote Similarity NPD3160 Suspended
0.5897 Remote Similarity NPD9577 Approved
0.5873 Remote Similarity NPD8865 Approved
0.5818 Remote Similarity NPD8869 Approved
0.5763 Remote Similarity NPD329 Discontinued
0.5694 Remote Similarity NPD1825 Clinical (unspecified phase)
0.5694 Remote Similarity NPD2256 Clinical (unspecified phase)
0.5652 Remote Similarity NPD2263 Discontinued
0.5641 Remote Similarity NPD1125 Discovery
0.5636 Remote Similarity NPD8804 Approved
0.5636 Remote Similarity NPD8805 Approved
0.5616 Remote Similarity NPD9109 Discontinued
0.5616 Remote Similarity NPD366 Approved
0.5606 Remote Similarity NPD9014 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