Structure

Physi-Chem Properties

Molecular Weight:  242.09
Volume:  252.879
LogP:  4.223
LogD:  3.361
LogS:  -3.548
# Rotatable Bonds:  0
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.696
Synthetic Accessibility Score:  2.722
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.798
MDCK Permeability:  2.697690433706157e-05
Pgp-inhibitor:  0.021
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.151
Plasma Protein Binding (PPB):  99.60124969482422%
Volume Distribution (VD):  0.759
Pgp-substrate:  1.3960334062576294%

ADMET: Metabolism

CYP1A2-inhibitor:  0.956
CYP1A2-substrate:  0.645
CYP2C19-inhibitor:  0.37
CYP2C19-substrate:  0.378
CYP2C9-inhibitor:  0.561
CYP2C9-substrate:  0.811
CYP2D6-inhibitor:  0.827
CYP2D6-substrate:  0.491
CYP3A4-inhibitor:  0.478
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  3.466
Half-life (T1/2):  0.467

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.815
Drug-inuced Liver Injury (DILI):  0.479
AMES Toxicity:  0.048
Rat Oral Acute Toxicity:  0.851
Maximum Recommended Daily Dose:  0.389
Skin Sensitization:  0.929
Carcinogencity:  0.846
Eye Corrosion:  0.003
Eye Irritation:  0.703
Respiratory Toxicity:  0.764

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

  Natural Product: NPC192577

Natural Product ID:  NPC192577
Common Name*:   Alpha-Lapachone
IUPAC Name:   2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:   Alpha-Lapachone
Standard InCHIKey:  PJWHOPKRRBUSDH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H14O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-6H,7-8H2,1-2H3
SMILES:  O=C1C2=C(CCC(O2)(C)C)C(=O)c2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL441441
PubChem CID:   72732
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans
        • [CHEMONTID:0001641] Naphthopyranones

*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
NPO20768 Ekmanianthe longiflora Species Bignoniaceae Eukaryota roots n.a. n.a. PMID[10785421]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[17950604]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. bark n.a. PMID[17950604]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. Brazilian n.a. PMID[19674905]
NPO9835 Catalpa ovata Species Bignoniaceae Eukaryota stem bark Medicinal Plant Garden, College of Pharmacy, Ewha Womans University 2013-DEC PMID[28787158]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[32044231]
NPO9835 Catalpa ovata Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[9599262]
NPO9835 Catalpa ovata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9835 Catalpa ovata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9835 Catalpa ovata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20768 Ekmanianthe longiflora Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12083 Hydnellum zonatum Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3751 Orthantha lutea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9835 Catalpa ovata Species Bignoniaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 13460.0 nM PMID[502401]
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens IC50 = 4340.0 nM PMID[502402]
NPT1851 Cell Line Col2 Homo sapiens ED50 = 9.9 ug ml-1 PMID[502404]
NPT91 Cell Line KB Homo sapiens ED50 = 13.0 ug ml-1 PMID[502404]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 7.1 ug ml-1 PMID[502404]
NPT2345 Cell Line SW626 Homo sapiens ED50 = 3.0 ug ml-1 PMID[502404]
NPT136 Cell Line SK-N-SH Homo sapiens ED50 = 5.1 ug ml-1 PMID[502404]
NPT726 Cell Line M109 Mus musculus ED50 = 9.0 ug ml-1 PMID[502404]
NPT1851 Cell Line Col2 Homo sapiens IC50 = 40900.0 nM PMID[502407]
NPT91 Cell Line KB Homo sapiens IC50 = 53700.0 nM PMID[502407]
NPT858 Cell Line LNCaP Homo sapiens IC50 = 29300.0 nM PMID[502407]
NPT1034 Cell Line Lu1 Homo sapiens IC50 = 21900.0 nM PMID[502407]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 38000.0 nM PMID[502407]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 7900.0 nM PMID[502407]
NPT168 Cell Line P388 Mus musculus IC50 = 800.0 nM PMID[502407]
NPT2345 Cell Line SW626 Homo sapiens IC50 = 12400.0 nM PMID[502407]
NPT2345 Cell Line SW626 Homo sapiens Inhibition = 0.0 % PMID[502407]
NPT2345 Cell Line SW626 Homo sapiens Inhibition = 10.3 % PMID[502407]
NPT941 Cell Line HaCaT Homo sapiens IC50 = 10000.0 nM PMID[502408]
NPT179 Cell Line A2780 Homo sapiens GI50 = 4000.0 nM PMID[502409]
NPT1723 Cell Line HBL-100 Homo sapiens GI50 = 14000.0 nM PMID[502409]
NPT165 Cell Line HeLa Homo sapiens GI50 = 15000.0 nM PMID[502409]
NPT1577 Cell Line SW1573 Homo sapiens GI50 = 3100.0 nM PMID[502409]
NPT396 Cell Line T47D Homo sapiens GI50 = 25000.0 nM PMID[502409]
NPT1183 Cell Line WiDr Homo sapiens GI50 = 26000.0 nM PMID[502409]
NPT1723 Cell Line HBL-100 Homo sapiens GI50 = 14000.0 nM PMID[502410]
NPT165 Cell Line HeLa Homo sapiens GI50 = 15000.0 nM PMID[502410]
NPT1577 Cell Line SW1573 Homo sapiens GI50 = 3100.0 nM PMID[502410]
NPT1183 Cell Line WiDr Homo sapiens GI50 = 26000.0 nM PMID[502410]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 1200.0 nM PMID[502411]
NPT165 Cell Line HeLa Homo sapiens GI50 = 25000.0 nM PMID[502412]
NPT15 Cell Line Jurkat Homo sapiens GI50 = 75000.0 nM PMID[502412]
NPT15 Cell Line Jurkat Homo sapiens Activity = 7.4 % PMID[502412]
NPT81 Cell Line A549 Homo sapiens GI50 = 16300.0 nM PMID[502412]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 = 4700.0 nM PMID[502412]
NPT114 Cell Line LoVo Homo sapiens GI50 = 24400.0 nM PMID[502412]
NPT306 Cell Line PC-3 Homo sapiens GI50 = 13000.0 nM PMID[502412]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 8180.0 nM PMID[502415]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 19110.0 nM PMID[502415]
NPT381 Cell Line OVCAR-8 Homo sapiens IC50 = 14790.0 nM PMID[502415]
NPT399 Cell Line SF-295 Homo sapiens IC50 = 18770.0 nM PMID[502415]
NPT927 Cell Line PBMC Homo sapiens IC50 > 20660.0 nM PMID[502415]
NPT171 Cell Line MRC5 Homo sapiens IC50 > 100000.0 nM PMID[502416]
NPT2936 Individual Protein NADPH--cytochrome P450 reductase Homo sapiens Activity = 1010.0 micromol/min PMID[502417]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 10000.0 nM PMID[502418]
NPT111 Cell Line K562 Homo sapiens IC50 > 10000.0 nM PMID[502418]
NPT1182 Cell Line J774.A1 Mus musculus IC50 = 285.0 ug.mL-1 PMID[502420]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 30000.0 nM PMID[502421]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 30000.0 nM PMID[502421]
NPT81 Cell Line A549 Homo sapiens IC50 > 30000.0 nM PMID[502421]
NPT32 Organism Mus musculus Mus musculus Lysis = 48.0 % PMID[502400]
NPT35 Others n.a. LogP = 3.5 n.a. PMID[502401]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 210.0 nM PMID[502403]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 103.9 % PMID[502403]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 91.0 % PMID[502403]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 4.8 % PMID[502403]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 6.7 ug ml-1 PMID[502404]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 5.3 ug ml-1 PMID[502404]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 8.3 ug ml-1 PMID[502404]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 12.9 ug ml-1 PMID[502404]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 4800000.0 nM PMID[502405]
NPT35 Others n.a. Activity = 1.0 microM/min PMID[502406]
NPT35 Others n.a. Activity = 7.0 microM/min PMID[502406]
NPT1266 Organism Leptomonas seymouri Leptomonas seymouri IC50 = 4100.0 nM PMID[502406]
NPT1267 Organism Crithidia fasciculata Crithidia fasciculata IC50 = 27000.0 nM PMID[502406]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 27700.0 nM PMID[502407]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 34300.0 nM PMID[502407]
NPT32 Organism Mus musculus Mus musculus Activity = 0.3 g PMID[502407]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 82.7 % PMID[502411]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 3190.0 nM PMID[502411]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 16700.0 nM PMID[502412]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 23100.0 nM PMID[502412]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 9000.0 nM PMID[502412]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 22700.0 nM PMID[502412]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 28700.0 nM PMID[502413]
NPT2 Others Unspecified Ratio CC50/IC50 = 0.25 n.a. PMID[502414]
NPT2 Others Unspecified Ratio CC50/IC50 = 0.24 n.a. PMID[502414]
NPT2 Others Unspecified Ratio CC50/IC50 = 0.65 n.a. PMID[502414]
NPT2 Others Unspecified Ratio CC50/IC50 = 0.27 n.a. PMID[502414]
NPT27 Others Unspecified CC50 = 3800.0 nM PMID[502414]
NPT634 Organism Leishmania amazonensis Leishmania amazonensis IC50 = 15150.0 nM PMID[502414]
NPT634 Organism Leishmania amazonensis Leishmania amazonensis IC50 = 16080.0 nM PMID[502414]
NPT1021 Organism Leishmania infantum Leishmania infantum IC50 = 5850.0 nM PMID[502414]
NPT1021 Organism Leishmania infantum Leishmania infantum IC50 = 13880.0 nM PMID[502414]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 50000.0 nM PMID[502416]
NPT935 Individual Protein Quinone reductase 1) Homo sapiens Activity = 719.0 micromol/min PMID[502417]
NPT2 Others Unspecified Selectivity ratio = 0.72 n.a. PMID[502417]
NPT35 Others n.a. Activity = -1.22 V PMID[502417]
NPT25570 SINGLE PROTEIN Dihydroorotate dehydrogenase (quinone), mitochondrial Schistosoma mansoni Activity = 68.1 % PMID[502419]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 103.3 ug.mL-1 PMID[502420]

☑ 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 NPC192577 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
0.9423 High Similarity NPC137315
0.9423 High Similarity NPC291799
0.9109 High Similarity NPC112552
0.8932 High Similarity NPC274443
0.8835 High Similarity NPC244427
0.8835 High Similarity NPC222390
0.8807 High Similarity NPC241851
0.8807 High Similarity NPC326664
0.8796 High Similarity NPC212415
0.8774 High Similarity NPC470391
0.8774 High Similarity NPC203732
0.8762 High Similarity NPC172483
0.8727 High Similarity NPC470764
0.8696 High Similarity NPC65627
0.8596 High Similarity NPC105709
0.8482 Intermediate Similarity NPC62138
0.8468 Intermediate Similarity NPC67377
0.8455 Intermediate Similarity NPC292834
0.8447 Intermediate Similarity NPC156021
0.8304 Intermediate Similarity NPC196075
0.8241 Intermediate Similarity NPC134120
0.8214 Intermediate Similarity NPC143768
0.8214 Intermediate Similarity NPC13784
0.82 Intermediate Similarity NPC157778
0.8173 Intermediate Similarity NPC12695
0.8142 Intermediate Similarity NPC477411
0.8137 Intermediate Similarity NPC476484
0.81 Intermediate Similarity NPC43945
0.8099 Intermediate Similarity NPC81135
0.807 Intermediate Similarity NPC228936
0.8039 Intermediate Similarity NPC173413
0.8034 Intermediate Similarity NPC204784
0.8019 Intermediate Similarity NPC145052
0.8 Intermediate Similarity NPC135730
0.8 Intermediate Similarity NPC260886
0.8 Intermediate Similarity NPC100767
0.8 Intermediate Similarity NPC226093
0.7966 Intermediate Similarity NPC232958
0.7965 Intermediate Similarity NPC186128
0.7961 Intermediate Similarity NPC284475
0.7949 Intermediate Similarity NPC318173
0.7937 Intermediate Similarity NPC171968
0.7931 Intermediate Similarity NPC469843
0.7925 Intermediate Similarity NPC103048
0.7913 Intermediate Similarity NPC474408
0.7909 Intermediate Similarity NPC209632
0.789 Intermediate Similarity NPC247976
0.7885 Intermediate Similarity NPC188844
0.7885 Intermediate Similarity NPC1682
0.7885 Intermediate Similarity NPC155232
0.7869 Intermediate Similarity NPC236405
0.7864 Intermediate Similarity NPC303967
0.7864 Intermediate Similarity NPC110420
0.7864 Intermediate Similarity NPC19256
0.7864 Intermediate Similarity NPC67585
0.7863 Intermediate Similarity NPC222968
0.7863 Intermediate Similarity NPC80605
0.7863 Intermediate Similarity NPC268930
0.7863 Intermediate Similarity NPC323440
0.7851 Intermediate Similarity NPC318067
0.7851 Intermediate Similarity NPC328107
0.7818 Intermediate Similarity NPC114594
0.7818 Intermediate Similarity NPC329282
0.7815 Intermediate Similarity NPC476225
0.781 Intermediate Similarity NPC289883
0.781 Intermediate Similarity NPC238219
0.7788 Intermediate Similarity NPC133461
0.7787 Intermediate Similarity NPC295664
0.7768 Intermediate Similarity NPC470007
0.7759 Intermediate Similarity NPC474095
0.775 Intermediate Similarity NPC144547
0.7736 Intermediate Similarity NPC260233
0.7719 Intermediate Similarity NPC474057
0.7719 Intermediate Similarity NPC210089
0.7714 Intermediate Similarity NPC153885
0.7714 Intermediate Similarity NPC59677
0.7705 Intermediate Similarity NPC325740
0.77 Intermediate Similarity NPC215008
0.7699 Intermediate Similarity NPC269023
0.7699 Intermediate Similarity NPC99846
0.7692 Intermediate Similarity NPC301341
0.7692 Intermediate Similarity NPC284184
0.7685 Intermediate Similarity NPC75724
0.7685 Intermediate Similarity NPC49994
0.7685 Intermediate Similarity NPC134882
0.767 Intermediate Similarity NPC267262
0.7667 Intermediate Similarity NPC988
0.7667 Intermediate Similarity NPC289432
0.7647 Intermediate Similarity NPC307
0.7647 Intermediate Similarity NPC160339
0.7636 Intermediate Similarity NPC320891
0.7634 Intermediate Similarity NPC173980
0.76 Intermediate Similarity NPC478162
0.76 Intermediate Similarity NPC478165
0.7596 Intermediate Similarity NPC418308
0.7593 Intermediate Similarity NPC265220
0.7593 Intermediate Similarity NPC239185
0.7565 Intermediate Similarity NPC474157
0.7563 Intermediate Similarity NPC61651
0.7559 Intermediate Similarity NPC27659
0.7545 Intermediate Similarity NPC109514
0.7545 Intermediate Similarity NPC476993
0.7524 Intermediate Similarity NPC277277
0.7522 Intermediate Similarity NPC37622
0.7522 Intermediate Similarity NPC30594
0.7521 Intermediate Similarity NPC238861
0.7521 Intermediate Similarity NPC196673
0.7521 Intermediate Similarity NPC77000
0.7521 Intermediate Similarity NPC471721
0.75 Intermediate Similarity NPC280789
0.75 Intermediate Similarity NPC218855
0.748 Intermediate Similarity NPC471832
0.748 Intermediate Similarity NPC164947
0.7477 Intermediate Similarity NPC34243
0.7459 Intermediate Similarity NPC472981
0.7458 Intermediate Similarity NPC93181
0.7458 Intermediate Similarity NPC217111
0.7455 Intermediate Similarity NPC476042
0.7453 Intermediate Similarity NPC110704
0.744 Intermediate Similarity NPC294050
0.744 Intermediate Similarity NPC328997
0.7438 Intermediate Similarity NPC476645
0.7436 Intermediate Similarity NPC470253
0.7436 Intermediate Similarity NPC272524
0.7436 Intermediate Similarity NPC469547
0.7436 Intermediate Similarity NPC471481
0.7419 Intermediate Similarity NPC51079
0.7419 Intermediate Similarity NPC135062
0.7417 Intermediate Similarity NPC471553
0.7414 Intermediate Similarity NPC265513
0.7411 Intermediate Similarity NPC329556
0.7411 Intermediate Similarity NPC60679
0.7407 Intermediate Similarity NPC472880
0.7402 Intermediate Similarity NPC237225
0.7381 Intermediate Similarity NPC177925
0.7373 Intermediate Similarity NPC234637
0.7373 Intermediate Similarity NPC130591
0.7373 Intermediate Similarity NPC308744
0.735 Intermediate Similarity NPC79496
0.7348 Intermediate Similarity NPC38158
0.7339 Intermediate Similarity NPC185208
0.7339 Intermediate Similarity NPC219573
0.7333 Intermediate Similarity NPC158157
0.7328 Intermediate Similarity NPC23894
0.7327 Intermediate Similarity NPC145053
0.7323 Intermediate Similarity NPC51448
0.7323 Intermediate Similarity NPC115797
0.7323 Intermediate Similarity NPC316553
0.7311 Intermediate Similarity NPC274839
0.7311 Intermediate Similarity NPC210092
0.7311 Intermediate Similarity NPC474685
0.7302 Intermediate Similarity NPC123506
0.73 Intermediate Similarity NPC300205
0.7295 Intermediate Similarity NPC202015
0.7293 Intermediate Similarity NPC264022
0.7288 Intermediate Similarity NPC93287
0.7287 Intermediate Similarity NPC198305
0.728 Intermediate Similarity NPC85511
0.7265 Intermediate Similarity NPC167504
0.7265 Intermediate Similarity NPC243355
0.7258 Intermediate Similarity NPC269923
0.7258 Intermediate Similarity NPC120545
0.7258 Intermediate Similarity NPC167323
0.7244 Intermediate Similarity NPC15837
0.7244 Intermediate Similarity NPC146239
0.7244 Intermediate Similarity NPC48992
0.7244 Intermediate Similarity NPC231774
0.7244 Intermediate Similarity NPC51037
0.7244 Intermediate Similarity NPC51292
0.7241 Intermediate Similarity NPC265407
0.7241 Intermediate Similarity NPC83628
0.7238 Intermediate Similarity NPC69057
0.7232 Intermediate Similarity NPC473325
0.7228 Intermediate Similarity NPC164086
0.7228 Intermediate Similarity NPC190567
0.7227 Intermediate Similarity NPC11824
0.7222 Intermediate Similarity NPC474766
0.7222 Intermediate Similarity NPC310540
0.7222 Intermediate Similarity NPC323420
0.7218 Intermediate Similarity NPC232996
0.7217 Intermediate Similarity NPC185763
0.7217 Intermediate Similarity NPC83409
0.7217 Intermediate Similarity NPC37914
0.7217 Intermediate Similarity NPC119271
0.7207 Intermediate Similarity NPC229242
0.72 Intermediate Similarity NPC285470
0.72 Intermediate Similarity NPC91478
0.72 Intermediate Similarity NPC36342
0.72 Intermediate Similarity NPC2785
0.7193 Intermediate Similarity NPC249067
0.7193 Intermediate Similarity NPC31786
0.7184 Intermediate Similarity NPC273758
0.7176 Intermediate Similarity NPC309430
0.717 Intermediate Similarity NPC477704
0.717 Intermediate Similarity NPC153308
0.717 Intermediate Similarity NPC477693
0.7168 Intermediate Similarity NPC45613
0.7168 Intermediate Similarity NPC25458
0.7167 Intermediate Similarity NPC186933
0.7167 Intermediate Similarity NPC472164

  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 NPC192577 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
0.8796 High Similarity NPD1609 Clinical (unspecified phase)
0.81 Intermediate Similarity NPD650 Approved
0.7961 Intermediate Similarity NPD7609 Phase 3
0.7885 Intermediate Similarity NPD7631 Approved
0.7603 Intermediate Similarity NPD4879 Approved
0.7593 Intermediate Similarity NPD3495 Discontinued
0.7521 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD1930 Approved
0.7411 Intermediate Similarity NPD1929 Approved
0.7311 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD2066 Phase 3
0.7222 Intermediate Similarity NPD1508 Approved
0.7193 Intermediate Similarity NPD1237 Approved
0.7193 Intermediate Similarity NPD164 Approved
0.7177 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD1932 Approved
0.7157 Intermediate Similarity NPD942 Approved
0.7119 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD1471 Phase 3
0.7094 Intermediate Similarity NPD2182 Approved
0.7075 Intermediate Similarity NPD1087 Approved
0.7043 Intermediate Similarity NPD5909 Discontinued
0.7027 Intermediate Similarity NPD1843 Approved
0.7027 Intermediate Similarity NPD1989 Approved
0.7025 Intermediate Similarity NPD5951 Approved
0.7 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6949 Remote Similarity NPD2329 Discontinued
0.6937 Remote Similarity NPD688 Clinical (unspecified phase)
0.6937 Remote Similarity NPD1693 Approved
0.6935 Remote Similarity NPD7009 Phase 2
0.6929 Remote Similarity NPD3972 Approved
0.6929 Remote Similarity NPD4878 Approved
0.6891 Remote Similarity NPD2067 Discontinued
0.6881 Remote Similarity NPD1086 Approved
0.6881 Remote Similarity NPD1090 Approved
0.6881 Remote Similarity NPD1089 Approved
0.686 Remote Similarity NPD6858 Approved
0.686 Remote Similarity NPD7094 Approved
0.6855 Remote Similarity NPD7610 Discontinued
0.6847 Remote Similarity NPD1202 Approved
0.6847 Remote Similarity NPD1563 Approved
0.6842 Remote Similarity NPD7961 Discontinued
0.6842 Remote Similarity NPD1238 Approved
0.6825 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6822 Remote Similarity NPD9259 Approved
0.6822 Remote Similarity NPD9257 Approved
0.6822 Remote Similarity NPD1876 Approved
0.6818 Remote Similarity NPD1239 Approved
0.6803 Remote Similarity NPD1241 Discontinued
0.6796 Remote Similarity NPD9490 Approved
0.6789 Remote Similarity NPD800 Approved
0.6774 Remote Similarity NPD405 Clinical (unspecified phase)
0.6769 Remote Similarity NPD1470 Approved
0.6757 Remote Similarity NPD1088 Approved
0.6738 Remote Similarity NPD7236 Approved
0.6731 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6719 Remote Similarity NPD1201 Approved
0.6698 Remote Similarity NPD9491 Approved
0.6667 Remote Similarity NPD1565 Approved
0.6667 Remote Similarity NPD1566 Phase 3
0.6667 Remote Similarity NPD1564 Approved
0.6614 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6612 Remote Similarity NPD1317 Discontinued
0.6606 Remote Similarity NPD506 Clinical (unspecified phase)
0.6591 Remote Similarity NPD2798 Approved
0.6589 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6577 Remote Similarity NPD3672 Approved
0.6577 Remote Similarity NPD9256 Approved
0.6577 Remote Similarity NPD9258 Approved
0.6577 Remote Similarity NPD3673 Approved
0.6573 Remote Similarity NPD3950 Discontinued
0.6567 Remote Similarity NPD5952 Clinical (unspecified phase)
0.656 Remote Similarity NPD3317 Approved
0.6538 Remote Similarity NPD225 Approved
0.6538 Remote Similarity NPD227 Approved
0.6507 Remote Similarity NPD7239 Suspended
0.65 Remote Similarity NPD2346 Discontinued
0.65 Remote Similarity NPD2355 Clinical (unspecified phase)
0.65 Remote Similarity NPD2353 Approved
0.6484 Remote Similarity NPD1651 Approved
0.6475 Remote Similarity NPD3748 Approved
0.6475 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6466 Remote Similarity NPD2788 Approved
0.6462 Remote Similarity NPD6287 Discontinued
0.6444 Remote Similarity NPD7008 Discontinued
0.6434 Remote Similarity NPD2345 Approved
0.6434 Remote Similarity NPD2932 Approved
0.6423 Remote Similarity NPD4307 Phase 2
0.6406 Remote Similarity NPD9545 Approved
0.6397 Remote Similarity NPD2313 Discontinued
0.6397 Remote Similarity NPD3764 Approved
0.6391 Remote Similarity NPD3266 Approved
0.6391 Remote Similarity NPD3267 Approved
0.6357 Remote Similarity NPD1245 Approved
0.6357 Remote Similarity NPD3025 Approved
0.6357 Remote Similarity NPD3024 Approved
0.6355 Remote Similarity NPD226 Approved
0.6349 Remote Similarity NPD1246 Approved
0.6349 Remote Similarity NPD2629 Approved
0.6348 Remote Similarity NPD9260 Approved
0.6343 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6336 Remote Similarity NPD1281 Approved
0.6325 Remote Similarity NPD9495 Approved
0.6319 Remote Similarity NPD3887 Approved
0.6319 Remote Similarity NPD2354 Approved
0.6312 Remote Similarity NPD2796 Approved
0.6311 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6308 Remote Similarity NPD3019 Approved
0.6308 Remote Similarity NPD17 Approved
0.6306 Remote Similarity NPD1282 Approved
0.6303 Remote Similarity NPD2193 Phase 2
0.6303 Remote Similarity NPD2648 Phase 3
0.6288 Remote Similarity NPD6637 Approved
0.6276 Remote Similarity NPD3300 Phase 2
0.627 Remote Similarity NPD6010 Discontinued
0.6268 Remote Similarity NPD2344 Approved
0.626 Remote Similarity NPD3023 Approved
0.626 Remote Similarity NPD3026 Approved
0.625 Remote Similarity NPD9261 Approved
0.625 Remote Similarity NPD3750 Approved
0.625 Remote Similarity NPD6647 Phase 2
0.6242 Remote Similarity NPD3226 Approved
0.6241 Remote Similarity NPD4308 Phase 3
0.6241 Remote Similarity NPD182 Clinical (unspecified phase)
0.6232 Remote Similarity NPD7713 Phase 3
0.6231 Remote Similarity NPD4105 Approved
0.6231 Remote Similarity NPD4102 Approved
0.6222 Remote Similarity NPD4980 Approved
0.6218 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6214 Remote Similarity NPD1607 Approved
0.6212 Remote Similarity NPD518 Clinical (unspecified phase)
0.621 Remote Similarity NPD664 Approved
0.621 Remote Similarity NPD3646 Clinical (unspecified phase)
0.621 Remote Similarity NPD1752 Approved
0.621 Remote Similarity NPD1756 Approved
0.6209 Remote Similarity NPD7057 Phase 3
0.6209 Remote Similarity NPD7058 Phase 2
0.6195 Remote Similarity NPD5347 Phase 2
0.6195 Remote Similarity NPD5346 Phase 2
0.6194 Remote Similarity NPD5667 Approved
0.6194 Remote Similarity NPD1283 Approved
0.619 Remote Similarity NPD2607 Approved
0.619 Remote Similarity NPD7410 Clinical (unspecified phase)
0.619 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6187 Remote Similarity NPD1240 Approved
0.6187 Remote Similarity NPD3140 Approved
0.6187 Remote Similarity NPD3142 Approved
0.6183 Remote Similarity NPD5306 Approved
0.6183 Remote Similarity NPD5305 Approved
0.6181 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6172 Remote Similarity NPD4198 Discontinued
0.6167 Remote Similarity NPD2196 Discontinued
0.6165 Remote Similarity NPD1608 Approved
0.6161 Remote Similarity NPD4793 Discontinued
0.6159 Remote Similarity NPD3268 Approved
0.6154 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6148 Remote Similarity NPD2797 Approved
0.6148 Remote Similarity NPD1018 Approved
0.6142 Remote Similarity NPD2652 Approved
0.6142 Remote Similarity NPD2650 Approved
0.6138 Remote Similarity NPD7003 Approved
0.6136 Remote Similarity NPD4136 Approved
0.6136 Remote Similarity NPD4106 Approved
0.6136 Remote Similarity NPD4135 Approved
0.6134 Remote Similarity NPD7798 Approved
0.6131 Remote Similarity NPD7055 Discontinued
0.6127 Remote Similarity NPD1510 Phase 2
0.6127 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6127 Remote Similarity NPD2799 Discontinued
0.6124 Remote Similarity NPD9493 Approved
0.6124 Remote Similarity NPD4574 Approved
0.6124 Remote Similarity NPD4576 Approved
0.6119 Remote Similarity NPD5157 Phase 1
0.6119 Remote Similarity NPD5159 Phase 2
0.6119 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6115 Remote Similarity NPD8032 Phase 2
0.6102 Remote Similarity NPD1100 Approved
0.6102 Remote Similarity NPD1099 Approved
0.6096 Remote Similarity NPD2309 Approved
0.6094 Remote Similarity NPD4766 Approved
0.6093 Remote Similarity NPD6599 Discontinued
0.609 Remote Similarity NPD4806 Approved
0.609 Remote Similarity NPD4807 Approved
0.6087 Remote Similarity NPD6039 Approved
0.608 Remote Similarity NPD4233 Approved
0.608 Remote Similarity NPD4234 Approved
0.6071 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6069 Remote Similarity NPD1243 Approved
0.6061 Remote Similarity NPD5836 Discontinued
0.6058 Remote Similarity NPD7084 Phase 3
0.6048 Remote Similarity NPD9264 Approved
0.6048 Remote Similarity NPD9267 Approved
0.6048 Remote Similarity NPD9263 Approved
0.6045 Remote Similarity NPD9717 Approved
0.604 Remote Similarity NPD5049 Phase 3
0.604 Remote Similarity NPD6273 Approved
0.6033 Remote Similarity NPD2171 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