Structure

Physi-Chem Properties

Molecular Weight:  328.87
Volume:  247.063
LogP:  5.716
LogD:  2.978
LogS:  -6.502
# Rotatable Bonds:  1
TPSA:  25.16
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.738
Synthetic Accessibility Score:  2.948
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.67
MDCK Permeability:  1.1893044757016469e-05
Pgp-inhibitor:  0.018
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.2
Plasma Protein Binding (PPB):  100.61804962158203%
Volume Distribution (VD):  3.872
Pgp-substrate:  1.4804238080978394%

ADMET: Metabolism

CYP1A2-inhibitor:  0.971
CYP1A2-substrate:  0.786
CYP2C19-inhibitor:  0.876
CYP2C19-substrate:  0.209
CYP2C9-inhibitor:  0.926
CYP2C9-substrate:  0.892
CYP2D6-inhibitor:  0.649
CYP2D6-substrate:  0.612
CYP3A4-inhibitor:  0.25
CYP3A4-substrate:  0.86

ADMET: Excretion

Clearance (CL):  6.135
Half-life (T1/2):  0.146

ADMET: Toxicity

hERG Blockers:  0.143
Human Hepatotoxicity (H-HT):  0.069
Drug-inuced Liver Injury (DILI):  0.916
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.332
Maximum Recommended Daily Dose:  0.927
Skin Sensitization:  0.788
Carcinogencity:  0.235
Eye Corrosion:  0.004
Eye Irritation:  0.224
Respiratory Toxicity:  0.347

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC156059

Natural Product ID:  NPC156059
Common Name*:   Neopyrrolomycin D
IUPAC Name:   4,5-dichloro-2-(2,3,4-trichloropyrrol-1-yl)phenol
Synonyms:   Neopyrrolomycin D
Standard InCHIKey:  RGDAAAZWUJXHMU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H4Cl5NO/c11-4-1-7(8(17)2-5(4)12)16-3-6(13)9(14)10(16)15/h1-3,17H
SMILES:  Clc1cc(c(cc1Cl)O)n1cc(c(c1Cl)Cl)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL549677
PubChem CID:   25243605
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002257] Substituted pyrroles
          • [CHEMONTID:0002334] Phenylpyrroles

*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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]

☑ 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
NPT3190 Cell Line NHDF Homo sapiens CC90 = 43.0 ug ml-1 PMID[491853]
NPT19 Organism Escherichia coli Escherichia coli MIC90 = 16.0 ug.mL-1 PMID[491853]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC90 = 16.0 ug.mL-1 PMID[491853]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC90 = 2.0 ug.mL-1 PMID[491853]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 8.0 ug ml-1 PMID[491853]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC90 = 32.0 ug.mL-1 PMID[491853]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC90 = 8.0 ug.mL-1 PMID[491853]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MIC90 = 4.0 ug.mL-1 PMID[491853]

☑ 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 NPC156059 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
0.9521 High Similarity NPC55038
0.9167 High Similarity NPC149402
0.7268 Intermediate Similarity NPC314940
0.7268 Intermediate Similarity NPC473764
0.7241 Intermediate Similarity NPC220523
0.7083 Intermediate Similarity NPC174421
0.6952 Remote Similarity NPC252590
0.6857 Remote Similarity NPC318935
0.6733 Remote Similarity NPC192315
0.67 Remote Similarity NPC476167
0.6684 Remote Similarity NPC42979
0.6667 Remote Similarity NPC224764
0.6667 Remote Similarity NPC25899
0.6632 Remote Similarity NPC184964
0.6632 Remote Similarity NPC96890
0.6631 Remote Similarity NPC48192
0.6627 Remote Similarity NPC151489
0.6597 Remote Similarity NPC253810
0.6578 Remote Similarity NPC120798
0.6567 Remote Similarity NPC469961
0.6558 Remote Similarity NPC197141
0.6543 Remote Similarity NPC79911
0.6541 Remote Similarity NPC63562
0.6534 Remote Similarity NPC328029
0.65 Remote Similarity NPC470404
0.65 Remote Similarity NPC470403
0.65 Remote Similarity NPC470394
0.6497 Remote Similarity NPC220765
0.649 Remote Similarity NPC475774
0.6482 Remote Similarity NPC171171
0.6471 Remote Similarity NPC132680
0.6471 Remote Similarity NPC269919
0.6465 Remote Similarity NPC204717
0.6457 Remote Similarity NPC300114
0.6442 Remote Similarity NPC470678
0.6432 Remote Similarity NPC295158
0.6432 Remote Similarity NPC314002
0.6429 Remote Similarity NPC470395
0.6402 Remote Similarity NPC322976
0.6402 Remote Similarity NPC63338
0.6402 Remote Similarity NPC324203
0.6381 Remote Similarity NPC472259
0.6368 Remote Similarity NPC59779
0.6368 Remote Similarity NPC471177
0.6368 Remote Similarity NPC46580
0.6368 Remote Similarity NPC124542
0.6364 Remote Similarity NPC219963
0.6364 Remote Similarity NPC266551
0.6364 Remote Similarity NPC161887
0.6359 Remote Similarity NPC257142
0.6335 Remote Similarity NPC263439
0.6335 Remote Similarity NPC211187
0.6302 Remote Similarity NPC471178
0.6276 Remote Similarity NPC95898
0.6274 Remote Similarity NPC477113
0.6257 Remote Similarity NPC284348
0.6245 Remote Similarity NPC177056
0.6244 Remote Similarity NPC99666
0.6244 Remote Similarity NPC324149
0.6239 Remote Similarity NPC142901
0.623 Remote Similarity NPC131718
0.6225 Remote Similarity NPC3715
0.6215 Remote Similarity NPC477111
0.6214 Remote Similarity NPC226202
0.6205 Remote Similarity NPC103687
0.6205 Remote Similarity NPC256828
0.6205 Remote Similarity NPC132631
0.6188 Remote Similarity NPC241025
0.6188 Remote Similarity NPC20249
0.6184 Remote Similarity NPC326634
0.6176 Remote Similarity NPC472289
0.6175 Remote Similarity NPC60553
0.6166 Remote Similarity NPC102423
0.6154 Remote Similarity NPC44161
0.6154 Remote Similarity NPC222018
0.6154 Remote Similarity NPC242209
0.615 Remote Similarity NPC478032
0.615 Remote Similarity NPC470500
0.6132 Remote Similarity NPC211813
0.6129 Remote Similarity NPC302159
0.6126 Remote Similarity NPC116573
0.6124 Remote Similarity NPC267928
0.6124 Remote Similarity NPC77555
0.6124 Remote Similarity NPC156704
0.6114 Remote Similarity NPC315491
0.6114 Remote Similarity NPC45459
0.6103 Remote Similarity NPC200836
0.6103 Remote Similarity NPC53144
0.6103 Remote Similarity NPC476138
0.6103 Remote Similarity NPC245816
0.6093 Remote Similarity NPC316403
0.6091 Remote Similarity NPC8022
0.6091 Remote Similarity NPC14651
0.6091 Remote Similarity NPC470799
0.6091 Remote Similarity NPC121658
0.6082 Remote Similarity NPC473057
0.607 Remote Similarity NPC478023
0.6058 Remote Similarity NPC84853
0.6058 Remote Similarity NPC329541
0.6053 Remote Similarity NPC36168
0.6047 Remote Similarity NPC476121
0.6047 Remote Similarity NPC476124
0.6044 Remote Similarity NPC471312
0.6042 Remote Similarity NPC212742
0.6041 Remote Similarity NPC476518
0.6038 Remote Similarity NPC213308
0.6038 Remote Similarity NPC19872
0.6029 Remote Similarity NPC93390
0.6018 Remote Similarity NPC477110
0.601 Remote Similarity NPC477591
0.601 Remote Similarity NPC48938
0.601 Remote Similarity NPC83381
0.6009 Remote Similarity NPC5145
0.6 Remote Similarity NPC140888
0.6 Remote Similarity NPC203754
0.6 Remote Similarity NPC150048
0.6 Remote Similarity NPC118511
0.6 Remote Similarity NPC475070
0.6 Remote Similarity NPC314573
0.6 Remote Similarity NPC251090
0.5991 Remote Similarity NPC18348
0.5991 Remote Similarity NPC287208
0.599 Remote Similarity NPC52831
0.599 Remote Similarity NPC325705
0.5981 Remote Similarity NPC106937
0.5981 Remote Similarity NPC307963
0.598 Remote Similarity NPC111624
0.598 Remote Similarity NPC313791
0.5972 Remote Similarity NPC473814
0.5972 Remote Similarity NPC78767
0.5962 Remote Similarity NPC92111
0.5957 Remote Similarity NPC476451
0.5951 Remote Similarity NPC42591
0.5943 Remote Similarity NPC212213
0.5942 Remote Similarity NPC110741
0.5942 Remote Similarity NPC32771
0.5942 Remote Similarity NPC296527
0.5941 Remote Similarity NPC72980
0.5939 Remote Similarity NPC108469
0.5938 Remote Similarity NPC313804
0.5938 Remote Similarity NPC315804
0.5936 Remote Similarity NPC85273
0.592 Remote Similarity NPC286195
0.5918 Remote Similarity NPC162268
0.5918 Remote Similarity NPC97367
0.5916 Remote Similarity NPC153769
0.5915 Remote Similarity NPC187558
0.5913 Remote Similarity NPC144381
0.5913 Remote Similarity NPC76748
0.5911 Remote Similarity NPC271792
0.5909 Remote Similarity NPC1527
0.5907 Remote Similarity NPC141353
0.5905 Remote Similarity NPC473821
0.5904 Remote Similarity NPC159856
0.59 Remote Similarity NPC474409
0.5899 Remote Similarity NPC306397
0.5899 Remote Similarity NPC212125
0.5899 Remote Similarity NPC165370
0.5896 Remote Similarity NPC90229
0.5874 Remote Similarity NPC288349
0.5872 Remote Similarity NPC88008
0.5872 Remote Similarity NPC183777
0.5869 Remote Similarity NPC472284
0.5867 Remote Similarity NPC177404
0.5856 Remote Similarity NPC256893
0.5856 Remote Similarity NPC476287
0.5855 Remote Similarity NPC33229
0.5855 Remote Similarity NPC35042
0.5853 Remote Similarity NPC165349
0.5853 Remote Similarity NPC47059
0.5853 Remote Similarity NPC118832
0.5853 Remote Similarity NPC329708
0.5853 Remote Similarity NPC274291
0.5853 Remote Similarity NPC264166
0.585 Remote Similarity NPC158129
0.5846 Remote Similarity NPC230869
0.5845 Remote Similarity NPC171787
0.5837 Remote Similarity NPC134079
0.5837 Remote Similarity NPC471593
0.5833 Remote Similarity NPC167908
0.5833 Remote Similarity NPC249662
0.5829 Remote Similarity NPC230403
0.5826 Remote Similarity NPC186351
0.5822 Remote Similarity NPC173080
0.5822 Remote Similarity NPC74153
0.5821 Remote Similarity NPC471294
0.5819 Remote Similarity NPC119006
0.5818 Remote Similarity NPC185782
0.5817 Remote Similarity NPC36498
0.5815 Remote Similarity NPC29702
0.5806 Remote Similarity NPC32002
0.5806 Remote Similarity NPC315348
0.5803 Remote Similarity NPC469763
0.5803 Remote Similarity NPC73952
0.5803 Remote Similarity NPC469760
0.5803 Remote Similarity NPC469765
0.5803 Remote Similarity NPC259644
0.5803 Remote Similarity NPC469786
0.5803 Remote Similarity NPC25008
0.58 Remote Similarity NPC164664

  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 NPC156059 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
0.7713 Intermediate Similarity NPD9689 Approved
0.7565 Intermediate Similarity NPD9687 Approved
0.7565 Intermediate Similarity NPD9688 Approved
0.7087 Intermediate Similarity NPD2615 Phase 3
0.7087 Intermediate Similarity NPD2616 Phase 3
0.7071 Intermediate Similarity NPD712 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD9690 Approved
0.7029 Intermediate Similarity NPD8823 Approved
0.701 Intermediate Similarity NPD408 Approved
0.6978 Remote Similarity NPD604 Clinical (unspecified phase)
0.694 Remote Similarity NPD9705 Discontinued
0.694 Remote Similarity NPD112 Approved
0.6888 Remote Similarity NPD1213 Phase 3
0.6827 Remote Similarity NPD1468 Clinical (unspecified phase)
0.6777 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6766 Remote Similarity NPD1229 Phase 2
0.6703 Remote Similarity NPD9706 Clinical (unspecified phase)
0.6683 Remote Similarity NPD3931 Approved
0.6683 Remote Similarity NPD3928 Approved
0.6617 Remote Similarity NPD9695 Approved
0.6588 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6587 Remote Similarity NPD3932 Clinical (unspecified phase)
0.6567 Remote Similarity NPD9243 Approved
0.6528 Remote Similarity NPD158 Discontinued
0.6514 Remote Similarity NPD1856 Discontinued
0.6476 Remote Similarity NPD3930 Clinical (unspecified phase)
0.6471 Remote Similarity NPD9382 Approved
0.6471 Remote Similarity NPD9383 Approved
0.6449 Remote Similarity NPD2772 Clinical (unspecified phase)
0.6449 Remote Similarity NPD2314 Clinical (unspecified phase)
0.6425 Remote Similarity NPD9548 Phase 2
0.6402 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6392 Remote Similarity NPD2077 Approved
0.6392 Remote Similarity NPD2076 Approved
0.6373 Remote Similarity NPD565 Phase 2
0.6369 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6345 Remote Similarity NPD1503 Clinical (unspecified phase)
0.6296 Remote Similarity NPD1322 Clinical (unspecified phase)
0.6293 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6275 Remote Similarity NPD4699 Discontinued
0.6269 Remote Similarity NPD424 Approved
0.6269 Remote Similarity NPD425 Approved
0.6263 Remote Similarity NPD5255 Approved
0.625 Remote Similarity NPD863 Approved
0.625 Remote Similarity NPD861 Approved
0.625 Remote Similarity NPD862 Approved
0.6202 Remote Similarity NPD7948 Phase 1
0.6173 Remote Similarity NPD2123 Phase 3
0.617 Remote Similarity NPD9596 Approved
0.617 Remote Similarity NPD9595 Approved
0.6165 Remote Similarity NPD4909 Approved
0.6135 Remote Similarity NPD4529 Approved
0.6135 Remote Similarity NPD4528 Approved
0.6135 Remote Similarity NPD4526 Approved
0.6134 Remote Similarity NPD926 Approved
0.6134 Remote Similarity NPD925 Approved
0.6132 Remote Similarity NPD6975 Discontinued
0.6131 Remote Similarity NPD6159 Phase 2
0.6127 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6127 Remote Similarity NPD1034 Phase 3
0.6114 Remote Similarity NPD1838 Clinical (unspecified phase)
0.6114 Remote Similarity NPD484 Approved
0.6108 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6095 Remote Similarity NPD3231 Approved
0.6094 Remote Similarity NPD1554 Clinical (unspecified phase)
0.6073 Remote Similarity NPD473 Clinical (unspecified phase)
0.6071 Remote Similarity NPD2781 Approved
0.6065 Remote Similarity NPD2739 Clinical (unspecified phase)
0.6064 Remote Similarity NPD1159 Approved
0.6062 Remote Similarity NPD7603 Discontinued
0.6061 Remote Similarity NPD4454 Phase 2
0.6051 Remote Similarity NPD2782 Approved
0.6051 Remote Similarity NPD2780 Approved
0.6048 Remote Similarity NPD691 Discontinued
0.603 Remote Similarity NPD5065 Approved
0.601 Remote Similarity NPD3116 Approved
0.601 Remote Similarity NPD3117 Approved
0.6008 Remote Similarity NPD1936 Clinical (unspecified phase)
0.6 Remote Similarity NPD3478 Clinical (unspecified phase)
0.6 Remote Similarity NPD3477 Phase 2
0.5991 Remote Similarity NPD4548 Discontinued
0.599 Remote Similarity NPD9510 Approved
0.599 Remote Similarity NPD6872 Clinical (unspecified phase)
0.5981 Remote Similarity NPD1038 Approved
0.5981 Remote Similarity NPD802 Phase 2
0.5975 Remote Similarity NPD7405 Clinical (unspecified phase)
0.5974 Remote Similarity NPD4296 Phase 2
0.5971 Remote Similarity NPD6393 Clinical (unspecified phase)
0.5971 Remote Similarity NPD2383 Phase 1
0.5962 Remote Similarity NPD938 Approved
0.596 Remote Similarity NPD5319 Approved
0.596 Remote Similarity NPD5320 Approved
0.5959 Remote Similarity NPD2582 Approved
0.5959 Remote Similarity NPD9574 Clinical (unspecified phase)
0.5959 Remote Similarity NPD2581 Approved
0.5946 Remote Similarity NPD165 Phase 2
0.5943 Remote Similarity NPD2727 Phase 2
0.5941 Remote Similarity NPD937 Clinical (unspecified phase)
0.5938 Remote Similarity NPD3514 Clinical (unspecified phase)
0.5934 Remote Similarity NPD7659 Discontinued
0.5933 Remote Similarity NPD6569 Phase 2
0.5931 Remote Similarity NPD7705 Clinical (unspecified phase)
0.5928 Remote Similarity NPD704 Clinical (unspecified phase)
0.5924 Remote Similarity NPD1704 Clinical (unspecified phase)
0.5923 Remote Similarity NPD3338 Clinical (unspecified phase)
0.5917 Remote Similarity NPD4303 Clinical (unspecified phase)
0.5915 Remote Similarity NPD2175 Phase 3
0.5915 Remote Similarity NPD2176 Approved
0.5915 Remote Similarity NPD2177 Approved
0.5907 Remote Similarity NPD5495 Phase 2
0.5907 Remote Similarity NPD7413 Phase 3
0.5907 Remote Similarity NPD1187 Discontinued
0.5902 Remote Similarity NPD5892 Approved
0.5899 Remote Similarity NPD9080 Approved
0.5899 Remote Similarity NPD9284 Approved
0.5897 Remote Similarity NPD4344 Clinical (unspecified phase)
0.5897 Remote Similarity NPD4343 Phase 1
0.5896 Remote Similarity NPD9530 Clinical (unspecified phase)
0.5895 Remote Similarity NPD4845 Discontinued
0.5892 Remote Similarity NPD945 Clinical (unspecified phase)
0.5867 Remote Similarity NPD972 Clinical (unspecified phase)
0.5859 Remote Similarity NPD8356 Approved
0.5857 Remote Similarity NPD5317 Clinical (unspecified phase)
0.5853 Remote Similarity NPD31 Approved
0.5853 Remote Similarity NPD4033 Approved
0.5853 Remote Similarity NPD4122 Approved
0.5853 Remote Similarity NPD4038 Approved
0.5853 Remote Similarity NPD4035 Approved
0.5853 Remote Similarity NPD4034 Approved
0.5853 Remote Similarity NPD4039 Approved
0.5853 Remote Similarity NPD4036 Approved
0.5853 Remote Similarity NPD32 Approved
0.5853 Remote Similarity NPD4037 Approved
0.5851 Remote Similarity NPD3813 Approved
0.5848 Remote Similarity NPD6710 Phase 3
0.5838 Remote Similarity NPD852 Discontinued
0.5829 Remote Similarity NPD1304 Clinical (unspecified phase)
0.5826 Remote Similarity NPD8430 Approved
0.5822 Remote Similarity NPD8405 Clinical (unspecified phase)
0.5817 Remote Similarity NPD9363 Approved
0.5817 Remote Similarity NPD9364 Phase 2
0.5814 Remote Similarity NPD2536 Discontinued
0.5813 Remote Similarity NPD5751 Clinical (unspecified phase)
0.5812 Remote Similarity NPD5538 Clinical (unspecified phase)
0.5808 Remote Similarity NPD7586 Clinical (unspecified phase)
0.5806 Remote Similarity NPD2073 Approved
0.5806 Remote Similarity NPD2074 Approved
0.5806 Remote Similarity NPD2075 Approved
0.5806 Remote Similarity NPD2072 Approved
0.5806 Remote Similarity NPD9245 Clinical (unspecified phase)
0.5805 Remote Similarity NPD4011 Clinical (unspecified phase)
0.5804 Remote Similarity NPD5612 Discontinued
0.5804 Remote Similarity NPD7112 Discontinued
0.5802 Remote Similarity NPD3791 Clinical (unspecified phase)
0.5802 Remote Similarity NPD1951 Clinical (unspecified phase)
0.5799 Remote Similarity NPD1392 Approved
0.5796 Remote Similarity NPD2785 Clinical (unspecified phase)
0.5795 Remote Similarity NPD2865 Clinical (unspecified phase)
0.5794 Remote Similarity NPD772 Phase 3
0.5792 Remote Similarity NPD4422 Phase 1
0.5789 Remote Similarity NPD7219 Approved
0.5789 Remote Similarity NPD7221 Approved
0.5784 Remote Similarity NPD1620 Clinical (unspecified phase)
0.5784 Remote Similarity NPD9506 Approved
0.578 Remote Similarity NPD3397 Phase 2
0.5778 Remote Similarity NPD1095 Clinical (unspecified phase)
0.5777 Remote Similarity NPD5522 Clinical (unspecified phase)
0.5775 Remote Similarity NPD1649 Discontinued
0.5773 Remote Similarity NPD2165 Phase 1
0.5771 Remote Similarity NPD5934 Clinical (unspecified phase)
0.5769 Remote Similarity NPD706 Phase 1
0.5769 Remote Similarity NPD3039 Clinical (unspecified phase)
0.5767 Remote Similarity NPD5999 Phase 2
0.5766 Remote Similarity NPD3570 Phase 2
0.5762 Remote Similarity NPD4081 Clinical (unspecified phase)
0.576 Remote Similarity NPD5669 Clinical (unspecified phase)
0.5759 Remote Similarity NPD4703 Approved
0.5759 Remote Similarity NPD4702 Approved
0.5756 Remote Similarity NPD6452 Discontinued
0.5753 Remote Similarity NPD4305 Clinical (unspecified phase)
0.5753 Remote Similarity NPD6728 Phase 3
0.5751 Remote Similarity NPD1467 Approved
0.5751 Remote Similarity NPD1466 Phase 3
0.5748 Remote Similarity NPD1622 Discontinued
0.5744 Remote Similarity NPD3114 Approved
0.5744 Remote Similarity NPD3115 Approved
0.5744 Remote Similarity NPD3113 Approved
0.5744 Remote Similarity NPD3112 Approved
0.5741 Remote Similarity NPD6219 Discontinued
0.574 Remote Similarity NPD3976 Clinical (unspecified phase)
0.574 Remote Similarity NPD3330 Phase 1
0.5739 Remote Similarity NPD4890 Phase 2
0.5735 Remote Similarity NPD954 Phase 1
0.5729 Remote Similarity NPD1568 Clinical (unspecified phase)
0.5728 Remote Similarity NPD3395 Approved
0.5728 Remote Similarity NPD3396 Approved
0.5728 Remote Similarity NPD7414 Clinical (unspecified phase)
0.5727 Remote Similarity NPD7453 Approved
0.5727 Remote Similarity NPD7222 Phase 2
0.5727 Remote Similarity NPD7452 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