Structure

Physi-Chem Properties

Molecular Weight:  328.87
Volume:  247.063
LogP:  5.595
LogD:  2.814
LogS:  -6.538
# 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:  2.997
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:  -4.608
MDCK Permeability:  8.994472409540322e-06
Pgp-inhibitor:  0.007
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.274
Plasma Protein Binding (PPB):  100.66967010498047%
Volume Distribution (VD):  3.246
Pgp-substrate:  1.3357657194137573%

ADMET: Metabolism

CYP1A2-inhibitor:  0.964
CYP1A2-substrate:  0.828
CYP2C19-inhibitor:  0.872
CYP2C19-substrate:  0.434
CYP2C9-inhibitor:  0.943
CYP2C9-substrate:  0.912
CYP2D6-inhibitor:  0.743
CYP2D6-substrate:  0.481
CYP3A4-inhibitor:  0.235
CYP3A4-substrate:  0.91

ADMET: Excretion

Clearance (CL):  4.823
Half-life (T1/2):  0.216

ADMET: Toxicity

hERG Blockers:  0.105
Human Hepatotoxicity (H-HT):  0.087
Drug-inuced Liver Injury (DILI):  0.897
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.195
Maximum Recommended Daily Dose:  0.923
Skin Sensitization:  0.668
Carcinogencity:  0.192
Eye Corrosion:  0.004
Eye Irritation:  0.079
Respiratory Toxicity:  0.271

Download Data

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

  Natural Product: NPC149402

Natural Product ID:  NPC149402
Common Name*:   Neopyrrolomycin C
IUPAC Name:   3,5-dichloro-2-(2,3,4-trichloropyrrol-1-yl)phenol
Synonyms:   Neopyrrolomycin C
Standard InCHIKey:  ZSUVDKFLDHDMOZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H4Cl5NO/c11-4-1-5(12)9(7(17)2-4)16-3-6(13)8(14)10(16)15/h1-3,17H
SMILES:  c1c(cc(c(c1Cl)n1cc(c(c1Cl)Cl)Cl)O)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL553671
PubChem CID:   25243604
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. n.a. n.a. PMID[18081255]
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[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[465633]
NPT19 Organism Escherichia coli Escherichia coli MIC90 = 16.0 ug.mL-1 PMID[465633]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC90 = 16.0 ug.mL-1 PMID[465633]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC90 = 1.0 ug.mL-1 PMID[465633]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC90 = 2.0 ug.mL-1 PMID[465633]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 8.0 ug ml-1 PMID[465633]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC90 = 32.0 ug.mL-1 PMID[465633]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC90 = 8.0 ug.mL-1 PMID[465633]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MIC90 = 2.0 ug.mL-1 PMID[465633]

☑ 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 NPC149402 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
0.9515 High Similarity NPC55038
0.9167 High Similarity NPC156059
0.7238 Intermediate Similarity NPC314940
0.7238 Intermediate Similarity NPC473764
0.7209 Intermediate Similarity NPC220523
0.7198 Intermediate Similarity NPC252590
0.7048 Intermediate Similarity NPC174421
0.6821 Remote Similarity NPC318935
0.67 Remote Similarity NPC192315
0.6685 Remote Similarity NPC63562
0.6667 Remote Similarity NPC476167
0.665 Remote Similarity NPC470678
0.6649 Remote Similarity NPC42979
0.6632 Remote Similarity NPC224764
0.663 Remote Similarity NPC25899
0.6612 Remote Similarity NPC132680
0.6612 Remote Similarity NPC269919
0.6597 Remote Similarity NPC184964
0.6597 Remote Similarity NPC96890
0.6595 Remote Similarity NPC48192
0.6587 Remote Similarity NPC151489
0.6561 Remote Similarity NPC253810
0.6541 Remote Similarity NPC324203
0.6541 Remote Similarity NPC322976
0.6541 Remote Similarity NPC63338
0.6541 Remote Similarity NPC120798
0.6505 Remote Similarity NPC79911
0.6494 Remote Similarity NPC328029
0.6471 Remote Similarity NPC263439
0.6471 Remote Similarity NPC211187
0.6462 Remote Similarity NPC220765
0.6461 Remote Similarity NPC470394
0.6461 Remote Similarity NPC470403
0.6461 Remote Similarity NPC470404
0.6456 Remote Similarity NPC475774
0.6447 Remote Similarity NPC171171
0.6429 Remote Similarity NPC204717
0.6396 Remote Similarity NPC314002
0.6396 Remote Similarity NPC295158
0.6389 Remote Similarity NPC470395
0.6372 Remote Similarity NPC197141
0.635 Remote Similarity NPC3715
0.6346 Remote Similarity NPC472259
0.6335 Remote Similarity NPC256828
0.6332 Remote Similarity NPC46580
0.633 Remote Similarity NPC59779
0.633 Remote Similarity NPC471177
0.633 Remote Similarity NPC124542
0.6327 Remote Similarity NPC219963
0.6327 Remote Similarity NPC266551
0.6327 Remote Similarity NPC161887
0.6319 Remote Similarity NPC257142
0.6278 Remote Similarity NPC300114
0.6263 Remote Similarity NPC471178
0.6238 Remote Similarity NPC477113
0.6237 Remote Similarity NPC95898
0.6216 Remote Similarity NPC284348
0.6207 Remote Similarity NPC469961
0.6207 Remote Similarity NPC99666
0.6207 Remote Similarity NPC324149
0.6204 Remote Similarity NPC8022
0.6204 Remote Similarity NPC470799
0.619 Remote Similarity NPC131718
0.6179 Remote Similarity NPC477111
0.6176 Remote Similarity NPC226202
0.6171 Remote Similarity NPC103687
0.6171 Remote Similarity NPC132631
0.615 Remote Similarity NPC241025
0.615 Remote Similarity NPC20249
0.6146 Remote Similarity NPC326634
0.6139 Remote Similarity NPC472289
0.6133 Remote Similarity NPC60553
0.6129 Remote Similarity NPC142901
0.6126 Remote Similarity NPC102423
0.6117 Remote Similarity NPC242209
0.6117 Remote Similarity NPC222018
0.6114 Remote Similarity NPC470500
0.6114 Remote Similarity NPC44161
0.6111 Remote Similarity NPC140888
0.6111 Remote Similarity NPC52831
0.6111 Remote Similarity NPC325705
0.6111 Remote Similarity NPC478032
0.6111 Remote Similarity NPC271792
0.6095 Remote Similarity NPC211813
0.6087 Remote Similarity NPC77555
0.6087 Remote Similarity NPC302159
0.6087 Remote Similarity NPC156704
0.6087 Remote Similarity NPC267928
0.6085 Remote Similarity NPC116573
0.6077 Remote Similarity NPC45459
0.6077 Remote Similarity NPC315491
0.6068 Remote Similarity NPC93390
0.6066 Remote Similarity NPC245816
0.6066 Remote Similarity NPC53144
0.6066 Remote Similarity NPC200836
0.6066 Remote Similarity NPC476138
0.6056 Remote Similarity NPC316403
0.6051 Remote Similarity NPC121658
0.6051 Remote Similarity NPC14651
0.6042 Remote Similarity NPC473057
0.603 Remote Similarity NPC478023
0.6019 Remote Similarity NPC329541
0.6019 Remote Similarity NPC84853
0.6011 Remote Similarity NPC36168
0.601 Remote Similarity NPC78767
0.601 Remote Similarity NPC473814
0.6009 Remote Similarity NPC167908
0.6 Remote Similarity NPC471312
0.6 Remote Similarity NPC19872
0.6 Remote Similarity NPC476518
0.6 Remote Similarity NPC213308
0.6 Remote Similarity NPC177056
0.5982 Remote Similarity NPC477110
0.5972 Remote Similarity NPC5145
0.5971 Remote Similarity NPC471448
0.597 Remote Similarity NPC48938
0.5969 Remote Similarity NPC477591
0.5962 Remote Similarity NPC251090
0.5962 Remote Similarity NPC475070
0.5961 Remote Similarity NPC314573
0.596 Remote Similarity NPC203754
0.596 Remote Similarity NPC150048
0.5959 Remote Similarity NPC118511
0.5953 Remote Similarity NPC287208
0.5953 Remote Similarity NPC18348
0.5942 Remote Similarity NPC473821
0.5942 Remote Similarity NPC106937
0.5942 Remote Similarity NPC307963
0.5939 Remote Similarity NPC111624
0.5939 Remote Similarity NPC313791
0.5935 Remote Similarity NPC476124
0.5935 Remote Similarity NPC476121
0.5931 Remote Similarity NPC36498
0.5926 Remote Similarity NPC185782
0.5922 Remote Similarity NPC92111
0.5921 Remote Similarity NPC476451
0.5916 Remote Similarity NPC212742
0.5911 Remote Similarity NPC42591
0.5905 Remote Similarity NPC212213
0.5902 Remote Similarity NPC32771
0.5902 Remote Similarity NPC296527
0.5902 Remote Similarity NPC110741
0.5901 Remote Similarity NPC315804
0.5901 Remote Similarity NPC313804
0.59 Remote Similarity NPC72980
0.5899 Remote Similarity NPC85273
0.5879 Remote Similarity NPC286195
0.5877 Remote Similarity NPC187558
0.5876 Remote Similarity NPC97367
0.5874 Remote Similarity NPC144381
0.5874 Remote Similarity NPC76748
0.5873 Remote Similarity NPC153769
0.5867 Remote Similarity NPC1527
0.5864 Remote Similarity NPC141353
0.586 Remote Similarity NPC159856
0.5859 Remote Similarity NPC474409
0.5857 Remote Similarity NPC74153
0.5857 Remote Similarity NPC90229
0.5852 Remote Similarity NPC306397
0.5852 Remote Similarity NPC212125
0.5852 Remote Similarity NPC165370
0.5845 Remote Similarity NPC26679
0.5842 Remote Similarity NPC474798
0.5837 Remote Similarity NPC288349
0.5833 Remote Similarity NPC88008
0.5833 Remote Similarity NPC183777
0.5829 Remote Similarity NPC472284
0.5825 Remote Similarity NPC177404
0.5825 Remote Similarity NPC230805
0.5818 Remote Similarity NPC476287
0.5816 Remote Similarity NPC108469
0.5814 Remote Similarity NPC329708
0.5814 Remote Similarity NPC264166
0.5814 Remote Similarity NPC274291
0.5814 Remote Similarity NPC47059
0.5814 Remote Similarity NPC165349
0.5814 Remote Similarity NPC118832
0.5812 Remote Similarity NPC33229
0.581 Remote Similarity NPC256893
0.5808 Remote Similarity NPC158129
0.5806 Remote Similarity NPC171787
0.5806 Remote Similarity NPC476157
0.5803 Remote Similarity NPC230869
0.5797 Remote Similarity NPC471593
0.5797 Remote Similarity NPC134079
0.5795 Remote Similarity NPC162268
0.5792 Remote Similarity NPC249662
0.5789 Remote Similarity NPC186351
0.5789 Remote Similarity NPC230403
0.5785 Remote Similarity NPC173080
0.5783 Remote Similarity NPC119006
0.5781 Remote Similarity NPC115049
0.5779 Remote Similarity NPC247980
0.5779 Remote Similarity NPC471294
0.5771 Remote Similarity NPC166655
0.5769 Remote Similarity NPC29702
0.5761 Remote Similarity NPC315348
0.5761 Remote Similarity NPC32002
0.5759 Remote Similarity NPC469786
0.5759 Remote Similarity NPC25008

  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 NPC149402 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
0.7358 Intermediate Similarity NPD9688 Approved
0.7358 Intermediate Similarity NPD9687 Approved
0.7316 Intermediate Similarity NPD9689 Approved
0.712 Intermediate Similarity NPD1213 Phase 3
0.7027 Intermediate Similarity NPD9690 Approved
0.6949 Remote Similarity NPD9706 Clinical (unspecified phase)
0.6944 Remote Similarity NPD604 Clinical (unspecified phase)
0.6906 Remote Similarity NPD112 Approved
0.6906 Remote Similarity NPD9705 Discontinued
0.6904 Remote Similarity NPD1229 Phase 2
0.6897 Remote Similarity NPD8823 Approved
0.6869 Remote Similarity NPD712 Clinical (unspecified phase)
0.6804 Remote Similarity NPD408 Approved
0.6731 Remote Similarity NPD2616 Phase 3
0.6731 Remote Similarity NPD2615 Phase 3
0.6612 Remote Similarity NPD9382 Approved
0.6612 Remote Similarity NPD9383 Approved
0.6588 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6583 Remote Similarity NPD9695 Approved
0.6566 Remote Similarity NPD4699 Discontinued
0.6555 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6541 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6492 Remote Similarity NPD158 Discontinued
0.6488 Remote Similarity NPD3931 Approved
0.6488 Remote Similarity NPD3928 Approved
0.6481 Remote Similarity NPD1856 Discontinued
0.6476 Remote Similarity NPD1468 Clinical (unspecified phase)
0.645 Remote Similarity NPD4909 Approved
0.6394 Remote Similarity NPD3932 Clinical (unspecified phase)
0.6387 Remote Similarity NPD9548 Phase 2
0.6354 Remote Similarity NPD2077 Approved
0.6354 Remote Similarity NPD2076 Approved
0.6335 Remote Similarity NPD565 Phase 2
0.6333 Remote Similarity NPD2739 Clinical (unspecified phase)
0.6328 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6302 Remote Similarity NPD2123 Phase 3
0.6286 Remote Similarity NPD3930 Clinical (unspecified phase)
0.6262 Remote Similarity NPD2772 Clinical (unspecified phase)
0.6262 Remote Similarity NPD2314 Clinical (unspecified phase)
0.6256 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4454 Phase 2
0.623 Remote Similarity NPD424 Approved
0.623 Remote Similarity NPD425 Approved
0.6223 Remote Similarity NPD5255 Approved
0.6213 Remote Similarity NPD7405 Clinical (unspecified phase)
0.6211 Remote Similarity NPD863 Approved
0.6211 Remote Similarity NPD861 Approved
0.6211 Remote Similarity NPD862 Approved
0.6207 Remote Similarity NPD9243 Approved
0.6172 Remote Similarity NPD5495 Phase 2
0.6165 Remote Similarity NPD7948 Phase 1
0.6142 Remote Similarity NPD1503 Clinical (unspecified phase)
0.6129 Remote Similarity NPD9595 Approved
0.6129 Remote Similarity NPD9596 Approved
0.6111 Remote Similarity NPD9510 Approved
0.6111 Remote Similarity NPD1322 Clinical (unspecified phase)
0.6098 Remote Similarity NPD4526 Approved
0.6098 Remote Similarity NPD4529 Approved
0.6098 Remote Similarity NPD4528 Approved
0.6095 Remote Similarity NPD6975 Discontinued
0.6094 Remote Similarity NPD926 Approved
0.6094 Remote Similarity NPD925 Approved
0.6091 Remote Similarity NPD6159 Phase 2
0.6089 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6089 Remote Similarity NPD1034 Phase 3
0.6087 Remote Similarity NPD9530 Clinical (unspecified phase)
0.6077 Remote Similarity NPD484 Approved
0.6077 Remote Similarity NPD1838 Clinical (unspecified phase)
0.607 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6058 Remote Similarity NPD3231 Approved
0.6053 Remote Similarity NPD1554 Clinical (unspecified phase)
0.6031 Remote Similarity NPD2781 Approved
0.6027 Remote Similarity NPD7603 Discontinued
0.601 Remote Similarity NPD2780 Approved
0.601 Remote Similarity NPD2782 Approved
0.599 Remote Similarity NPD5065 Approved
0.5989 Remote Similarity NPD165 Phase 2
0.5975 Remote Similarity NPD1936 Clinical (unspecified phase)
0.5971 Remote Similarity NPD5317 Clinical (unspecified phase)
0.5962 Remote Similarity NPD3477 Phase 2
0.5962 Remote Similarity NPD3478 Clinical (unspecified phase)
0.5952 Remote Similarity NPD2805 Phase 2
0.5952 Remote Similarity NPD4548 Discontinued
0.5949 Remote Similarity NPD6872 Clinical (unspecified phase)
0.5942 Remote Similarity NPD802 Phase 2
0.5942 Remote Similarity NPD1038 Approved
0.5939 Remote Similarity NPD4296 Phase 2
0.5931 Remote Similarity NPD9364 Phase 2
0.5931 Remote Similarity NPD2383 Phase 1
0.5931 Remote Similarity NPD9363 Approved
0.5931 Remote Similarity NPD6393 Clinical (unspecified phase)
0.5922 Remote Similarity NPD938 Approved
0.5918 Remote Similarity NPD5319 Approved
0.5918 Remote Similarity NPD5320 Approved
0.5916 Remote Similarity NPD9574 Clinical (unspecified phase)
0.5916 Remote Similarity NPD2581 Approved
0.5916 Remote Similarity NPD2582 Approved
0.5901 Remote Similarity NPD3514 Clinical (unspecified phase)
0.5894 Remote Similarity NPD6569 Phase 2
0.5887 Remote Similarity NPD3338 Clinical (unspecified phase)
0.5885 Remote Similarity NPD1704 Clinical (unspecified phase)
0.5885 Remote Similarity NPD704 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4303 Clinical (unspecified phase)
0.5877 Remote Similarity NPD2177 Approved
0.5877 Remote Similarity NPD2175 Phase 3
0.5877 Remote Similarity NPD2176 Approved
0.5864 Remote Similarity NPD473 Clinical (unspecified phase)
0.5862 Remote Similarity NPD4344 Clinical (unspecified phase)
0.5862 Remote Similarity NPD4343 Phase 1
0.5862 Remote Similarity NPD5892 Approved
0.5859 Remote Similarity NPD4845 Discontinued
0.5855 Remote Similarity NPD1418 Phase 2
0.5852 Remote Similarity NPD1466 Phase 3
0.5852 Remote Similarity NPD1467 Approved
0.5852 Remote Similarity NPD9284 Approved
0.5852 Remote Similarity NPD9080 Approved
0.5847 Remote Similarity NPD9470 Clinical (unspecified phase)
0.5847 Remote Similarity NPD945 Clinical (unspecified phase)
0.5833 Remote Similarity NPD796 Phase 2
0.5825 Remote Similarity NPD9714 Clinical (unspecified phase)
0.5825 Remote Similarity NPD972 Clinical (unspecified phase)
0.5822 Remote Similarity NPD8356 Approved
0.5821 Remote Similarity NPD937 Clinical (unspecified phase)
0.5814 Remote Similarity NPD4038 Approved
0.5814 Remote Similarity NPD31 Approved
0.5814 Remote Similarity NPD4037 Approved
0.5814 Remote Similarity NPD4122 Approved
0.5814 Remote Similarity NPD4039 Approved
0.5814 Remote Similarity NPD32 Approved
0.5814 Remote Similarity NPD4034 Approved
0.5814 Remote Similarity NPD4036 Approved
0.5814 Remote Similarity NPD4035 Approved
0.5814 Remote Similarity NPD4033 Approved
0.5808 Remote Similarity NPD3116 Approved
0.5808 Remote Similarity NPD3117 Approved
0.5806 Remote Similarity NPD3813 Approved
0.5792 Remote Similarity NPD852 Discontinued
0.5789 Remote Similarity NPD1304 Clinical (unspecified phase)
0.5789 Remote Similarity NPD8430 Approved
0.5785 Remote Similarity NPD8405 Clinical (unspecified phase)
0.5781 Remote Similarity NPD7407 Discontinued
0.578 Remote Similarity NPD5397 Clinical (unspecified phase)
0.5775 Remote Similarity NPD2536 Discontinued
0.5771 Remote Similarity NPD5751 Clinical (unspecified phase)
0.5771 Remote Similarity NPD7586 Clinical (unspecified phase)
0.5768 Remote Similarity NPD7659 Discontinued
0.5767 Remote Similarity NPD1159 Approved
0.5767 Remote Similarity NPD5538 Clinical (unspecified phase)
0.5766 Remote Similarity NPD5612 Discontinued
0.5766 Remote Similarity NPD7112 Discontinued
0.5762 Remote Similarity NPD3791 Clinical (unspecified phase)
0.5762 Remote Similarity NPD1951 Clinical (unspecified phase)
0.5761 Remote Similarity NPD2075 Approved
0.5761 Remote Similarity NPD2072 Approved
0.5761 Remote Similarity NPD2073 Approved
0.5761 Remote Similarity NPD2074 Approved
0.576 Remote Similarity NPD1392 Approved
0.5759 Remote Similarity NPD2785 Clinical (unspecified phase)
0.5759 Remote Similarity NPD7203 Clinical (unspecified phase)
0.5758 Remote Similarity NPD7705 Clinical (unspecified phase)
0.5756 Remote Similarity NPD4422 Phase 1
0.5755 Remote Similarity NPD772 Phase 3
0.5755 Remote Similarity NPD2727 Phase 2
0.5753 Remote Similarity NPD5420 Discontinued
0.5743 Remote Similarity NPD1620 Clinical (unspecified phase)
0.5741 Remote Similarity NPD3397 Phase 2
0.5738 Remote Similarity NPD7413 Phase 3
0.5738 Remote Similarity NPD9506 Approved
0.5735 Remote Similarity NPD5522 Clinical (unspecified phase)
0.573 Remote Similarity NPD1095 Clinical (unspecified phase)
0.573 Remote Similarity NPD1649 Discontinued
0.5729 Remote Similarity NPD5934 Clinical (unspecified phase)
0.5728 Remote Similarity NPD3039 Clinical (unspecified phase)
0.5728 Remote Similarity NPD706 Phase 1
0.5728 Remote Similarity NPD5999 Phase 2
0.5727 Remote Similarity NPD3570 Phase 2
0.5721 Remote Similarity NPD3321 Discontinued
0.5721 Remote Similarity NPD4081 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6728 Phase 3
0.5714 Remote Similarity NPD4349 Approved
0.5714 Remote Similarity NPD4350 Approved
0.5714 Remote Similarity NPD4702 Approved
0.5714 Remote Similarity NPD6452 Discontinued
0.5714 Remote Similarity NPD4703 Approved
0.5708 Remote Similarity NPD7399 Clinical (unspecified phase)
0.5708 Remote Similarity NPD1622 Discontinued
0.5707 Remote Similarity NPD4484 Phase 1
0.5702 Remote Similarity NPD4890 Phase 2
0.5701 Remote Similarity NPD3330 Phase 1
0.5701 Remote Similarity NPD3976 Clinical (unspecified phase)
0.5701 Remote Similarity NPD6219 Discontinued
0.5694 Remote Similarity NPD2394 Phase 2
0.5694 Remote Similarity NPD954 Phase 1
0.5688 Remote Similarity NPD7452 Approved
0.5688 Remote Similarity NPD7222 Phase 2
0.5688 Remote Similarity NPD6290 Phase 2
0.5688 Remote Similarity NPD7453 Approved
0.5687 Remote Similarity NPD3396 Approved
0.5687 Remote Similarity NPD3395 Approved
0.5686 Remote Similarity NPD7414 Clinical (unspecified phase)

  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