Structure

Physi-Chem Properties

Molecular Weight:  249.08
Volume:  264.472
LogP:  2.634
LogD:  2.727
LogS:  -4.127
# Rotatable Bonds:  1
TPSA:  46.5
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.779
Synthetic Accessibility Score:  2.261
Fsp3:  0.062
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.646
MDCK Permeability:  2.163604585803114e-05
Pgp-inhibitor:  0.081
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.446
Plasma Protein Binding (PPB):  96.21659088134766%
Volume Distribution (VD):  0.446
Pgp-substrate:  2.6456713676452637%

ADMET: Metabolism

CYP1A2-inhibitor:  0.952
CYP1A2-substrate:  0.164
CYP2C19-inhibitor:  0.899
CYP2C19-substrate:  0.095
CYP2C9-inhibitor:  0.859
CYP2C9-substrate:  0.143
CYP2D6-inhibitor:  0.09
CYP2D6-substrate:  0.159
CYP3A4-inhibitor:  0.147
CYP3A4-substrate:  0.176

ADMET: Excretion

Clearance (CL):  1.408
Half-life (T1/2):  0.22

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.418
Drug-inuced Liver Injury (DILI):  0.961
AMES Toxicity:  0.866
Rat Oral Acute Toxicity:  0.221
Maximum Recommended Daily Dose:  0.279
Skin Sensitization:  0.893
Carcinogencity:  0.811
Eye Corrosion:  0.078
Eye Irritation:  0.978
Respiratory Toxicity:  0.59

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

  Natural Product: NPC192533

Natural Product ID:  NPC192533
Common Name*:   2-Anilinonaphthalene-1,4-Dione
IUPAC Name:   2-anilinonaphthalene-1,4-dione
Synonyms:   2-Phenylamino-[1,4]Naphthoquinone
Standard InCHIKey:  OPECBHGHSFBITB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H11NO2/c18-15-10-14(17-11-6-2-1-3-7-11)16(19)13-9-5-4-8-12(13)15/h1-10,17H
SMILES:  O=C1C(=CC(=O)c2c1cccc2)Nc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL84010
PubChem CID:   81124
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*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
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. PMID[18619266]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 17.8 nM PMID[536297]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 11220.2 nM PMID[536297]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 1000.0 nM PMID[536297]
NPT2741 Individual Protein Pyruvate kinase Leishmania mexicana Potency = 7079.5 nM PMID[536297]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 7079.5 nM PMID[536297]
NPT1253 Individual Protein Calpain 2 Sus scrofa IC50 = 6162.7 nM PMID[536297]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 70.8 nM PMID[536297]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 1584.9 nM PMID[536297]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 3539.7 nM PMID[536297]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 3162.3 nM PMID[536297]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 25118.9 nM PMID[536297]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 1778.3 nM PMID[536297]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 14125.4 nM PMID[536297]
NPT90 Cell Line DU-145 Homo sapiens EC50 = 4.0 ug.mL-1 PMID[536298]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 2.6 ug.mL-1 PMID[536298]
NPT550 Cell Line T-24 Homo sapiens EC50 = 1.2 ug.mL-1 PMID[536298]
NPT2711 Cell Line BALB/3T3 Mus musculus EC50 = 0.2 ug.mL-1 PMID[536298]
NPT2711 Cell Line BALB/3T3 Mus musculus Ratio EC50 = 0.05 n.a. PMID[536298]
NPT83 Cell Line MCF7 Homo sapiens Ratio EC50 = 0.08 n.a. PMID[536298]
NPT2711 Cell Line BALB/3T3 Mus musculus Ratio EC50 = 0.16 n.a. PMID[536298]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 12589.3 nM PMID[536297]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 18356.4 nM PMID[536297]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 79432.8 nM PMID[536297]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 14125.4 nM PMID[536297]
NPT1415 Individual Protein Heat shock factor protein 1 Mus musculus EC50 = 1260.0 nM PMID[536297]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus IC50 n.a. 81685.0 nM PMID[536297]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 7943.3 nM PMID[536297]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 2908.1 nM PMID[536297]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 12589.3 nM PMID[536297]
NPT1397 Cell Line INS1 Rattus norvegicus AC50 = 3970.0 nM PMID[536297]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 5011.9 nM PMID[536297]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 3981.1 nM PMID[536297]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 3380.8 nM PMID[536297]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 32642.7 nM PMID[536297]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 9466.2 nM PMID[536297]
NPT159 Individual Protein Aberrant vpr protein Human immunodeficiency virus 1 Potency n.a. 2511.9 nM PMID[536297]
NPT804 Cell Line HT-22 Mus musculus TC50 = 7000.0 nM PMID[536299]
NPT804 Cell Line HT-22 Mus musculus PD50 = 64.0 nM PMID[536299]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23109.3 nM PMID[536297]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 12995.3 nM PMID[536297]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 31250.0 nM PMID[536300]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 100000.0 nM PMID[536300]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 5520.0 nM PMID[536300]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.175 uM PMID[536301]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.189 uM PMID[536302]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 17782.8 nM PMID[536297]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 20596.2 nM PMID[536297]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 3981.1 nM PMID[536297]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 6513.1 nM PMID[536297]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 2238.7 nM PMID[536297]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.337 uM PMID[536301]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.389 uM PMID[536302]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.74 uM PMID[536301]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.323 uM PMID[536302]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.302 uM PMID[536301]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.325 uM PMID[536302]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.571 uM PMID[536301]
NPT1282 Individual Protein Microphthalmia-associated transcription factor Homo sapiens AbsAC40_uM = 0.394 uM PMID[536302]
NPT1098 Individual Protein Eyes absent homolog 2 Homo sapiens Potency n.a. 6013.0 nM PMID[536297]
NPT446 Individual Protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 100000.0 nM PMID[536297]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 10000.0 nM PMID[536305]
NPT171 Cell Line MRC5 Homo sapiens IC50 > 100000.0 nM PMID[536306]
NPT29 Organism Rattus norvegicus Rattus norvegicus EC50 = 239.0 nM PMID[536296]
NPT29 Organism Rattus norvegicus Rattus norvegicus Emax = 98.0 % PMID[536296]
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens EC50 = 1348.0 nM PMID[536297]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 656.1 nM PMID[536297]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 12589.3 nM PMID[536297]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[536297]
NPT2 Others Unspecified Potency = 32642.7 nM PMID[536297]
NPT2 Others Unspecified IC50 = 11694.0 nM PMID[536297]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 2511.9 nM PMID[536297]
NPT35 Others n.a. LogP = 1.55 n.a. PMID[536298]
NPT2 Others Unspecified Potency n.a. 20596.2 nM PMID[536297]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[536297]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 3548.1 nM PMID[536297]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2332.3 nM PMID[536297]
NPT2 Others Unspecified Potency n.a. 4466.8 nM PMID[536297]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 1471.6 nM PMID[536297]
NPT27 Others Unspecified TI = 109.0 n.a. PMID[536299]
NPT2 Others Unspecified Potency n.a. 16360.1 nM PMID[536297]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 14581.0 nM PMID[536297]
NPT2 Others Unspecified AC50 = 2370.0 nM PMID[536301]
NPT2 Others Unspecified AC50 = 1930.0 nM PMID[536302]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AC50 > 70000.0 nM PMID[536301]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AC50 > 70000.0 nM PMID[536302]
NPT2 Others Unspecified Potency n.a. 14581.0 nM PMID[536297]
NPT2 Others Unspecified AC50 = 7240.0 nM PMID[536301]
NPT2 Others Unspecified AC50 = 5310.0 nM PMID[536302]
NPT2 Others Unspecified Potency n.a. 7079.5 nM PMID[536297]
NPT2 Others Unspecified Potency n.a. 4256.9 nM PMID[536297]
NPT2 Others Unspecified AC50 > 70000.0 nM PMID[536303]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[536297]
NPT2 Others Unspecified AC50 = 5860.0 nM PMID[536301]
NPT2 Others Unspecified AC50 = 28400.0 nM PMID[536302]
NPT2 Others Unspecified AC50 = 2560.0 nM PMID[536301]
NPT2 Others Unspecified AC50 = 6210.0 nM PMID[536302]
NPT2 Others Unspecified AC50 = 1530.0 nM PMID[536301]
NPT2 Others Unspecified AC50 = 1180.0 nM PMID[536302]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AC50 = 51510.0 nM PMID[536301]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 25000.0 nM PMID[536305]
NPT2 Others Unspecified Potency n.a. 891.3 nM PMID[536297]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 6300.0 nM PMID[536306]
NPT2 Others Unspecified Ratio IC50 > 15.0 n.a. PMID[536306]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 62.5 ug.mL-1 PMID[536307]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 250.0 ug.mL-1 PMID[536307]

☑ 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 NPC192533 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
0.8583 High Similarity NPC209389
0.8548 High Similarity NPC268534
0.8387 Intermediate Similarity NPC279385
0.8387 Intermediate Similarity NPC179605
0.832 Intermediate Similarity NPC103292
0.8189 Intermediate Similarity NPC254698
0.8175 Intermediate Similarity NPC257490
0.8016 Intermediate Similarity NPC226143
0.7955 Intermediate Similarity NPC194562
0.7874 Intermediate Similarity NPC291962
0.7874 Intermediate Similarity NPC177684
0.7829 Intermediate Similarity NPC39818
0.7812 Intermediate Similarity NPC258531
0.7812 Intermediate Similarity NPC112373
0.7812 Intermediate Similarity NPC161956
0.7769 Intermediate Similarity NPC172170
0.7606 Intermediate Similarity NPC136002
0.7517 Intermediate Similarity NPC237649
0.7517 Intermediate Similarity NPC300596
0.7447 Intermediate Similarity NPC207554
0.7432 Intermediate Similarity NPC295021
0.7426 Intermediate Similarity NPC472245
0.7402 Intermediate Similarity NPC57051
0.7394 Intermediate Similarity NPC471574
0.7394 Intermediate Similarity NPC471164
0.7388 Intermediate Similarity NPC472244
0.7388 Intermediate Similarity NPC470343
0.7339 Intermediate Similarity NPC434
0.7339 Intermediate Similarity NPC79618
0.7333 Intermediate Similarity NPC322433
0.7241 Intermediate Similarity NPC130797
0.7236 Intermediate Similarity NPC38262
0.7226 Intermediate Similarity NPC150863
0.7174 Intermediate Similarity NPC280807
0.7174 Intermediate Similarity NPC314431
0.7163 Intermediate Similarity NPC300299
0.7161 Intermediate Similarity NPC115232
0.7153 Intermediate Similarity NPC2823
0.7103 Intermediate Similarity NPC472241
0.7051 Intermediate Similarity NPC71132
0.7034 Intermediate Similarity NPC43477
0.7029 Intermediate Similarity NPC58827
0.7029 Intermediate Similarity NPC72473
0.7029 Intermediate Similarity NPC307437
0.6972 Remote Similarity NPC316104
0.6972 Remote Similarity NPC162417
0.6972 Remote Similarity NPC253476
0.6966 Remote Similarity NPC472243
0.6966 Remote Similarity NPC242933
0.6959 Remote Similarity NPC472242
0.6957 Remote Similarity NPC119326
0.6929 Remote Similarity NPC179224
0.6923 Remote Similarity NPC173295
0.6918 Remote Similarity NPC471943
0.6897 Remote Similarity NPC83214
0.6887 Remote Similarity NPC144691
0.6855 Remote Similarity NPC70949
0.6831 Remote Similarity NPC40364
0.6813 Remote Similarity NPC472118
0.6809 Remote Similarity NPC477432
0.6779 Remote Similarity NPC470822
0.6777 Remote Similarity NPC291070
0.6777 Remote Similarity NPC246757
0.6776 Remote Similarity NPC13526
0.6772 Remote Similarity NPC167336
0.677 Remote Similarity NPC126676
0.677 Remote Similarity NPC469671
0.6761 Remote Similarity NPC316746
0.6753 Remote Similarity NPC251391
0.6744 Remote Similarity NPC302790
0.6735 Remote Similarity NPC315051
0.6728 Remote Similarity NPC252572
0.6713 Remote Similarity NPC53044
0.6711 Remote Similarity NPC105811
0.6694 Remote Similarity NPC108800
0.6688 Remote Similarity NPC117032
0.6667 Remote Similarity NPC314186
0.6667 Remote Similarity NPC19256
0.6667 Remote Similarity NPC229477
0.6667 Remote Similarity NPC55529
0.6667 Remote Similarity NPC475094
0.6647 Remote Similarity NPC117027
0.6646 Remote Similarity NPC151635
0.6643 Remote Similarity NPC314098
0.664 Remote Similarity NPC75496
0.6638 Remote Similarity NPC215008
0.6624 Remote Similarity NPC76982
0.662 Remote Similarity NPC122235
0.6606 Remote Similarity NPC284775
0.6604 Remote Similarity NPC293458
0.6604 Remote Similarity NPC214106
0.66 Remote Similarity NPC478040
0.6594 Remote Similarity NPC475915
0.6583 Remote Similarity NPC176858
0.6583 Remote Similarity NPC418308
0.6582 Remote Similarity NPC80681
0.6582 Remote Similarity NPC193410
0.6582 Remote Similarity NPC36495
0.6581 Remote Similarity NPC70406
0.6579 Remote Similarity NPC467188
0.6579 Remote Similarity NPC478039
0.6573 Remote Similarity NPC187231
0.6571 Remote Similarity NPC226794
0.6562 Remote Similarity NPC113056
0.6562 Remote Similarity NPC138293
0.656 Remote Similarity NPC49994
0.6558 Remote Similarity NPC123906
0.6555 Remote Similarity NPC43945
0.6543 Remote Similarity NPC223595
0.6543 Remote Similarity NPC224970
0.6543 Remote Similarity NPC167724
0.6541 Remote Similarity NPC248117
0.6541 Remote Similarity NPC93653
0.6535 Remote Similarity NPC291610
0.6529 Remote Similarity NPC191444
0.6527 Remote Similarity NPC477042
0.6524 Remote Similarity NPC177261
0.6522 Remote Similarity NPC150323
0.6522 Remote Similarity NPC130931
0.6519 Remote Similarity NPC213914
0.6519 Remote Similarity NPC123241
0.6519 Remote Similarity NPC61013
0.6519 Remote Similarity NPC222029
0.6516 Remote Similarity NPC313889
0.6516 Remote Similarity NPC314223
0.6512 Remote Similarity NPC324091
0.651 Remote Similarity NPC130251
0.6504 Remote Similarity NPC289883
0.6503 Remote Similarity NPC328590
0.65 Remote Similarity NPC157778
0.65 Remote Similarity NPC469741
0.65 Remote Similarity NPC267262
0.6496 Remote Similarity NPC229353
0.6478 Remote Similarity NPC276085
0.6475 Remote Similarity NPC284475
0.6471 Remote Similarity NPC49184
0.6471 Remote Similarity NPC470579
0.6471 Remote Similarity NPC133003
0.6467 Remote Similarity NPC301760
0.6467 Remote Similarity NPC316202
0.6462 Remote Similarity NPC473498
0.646 Remote Similarity NPC265100
0.6453 Remote Similarity NPC473666
0.6452 Remote Similarity NPC473329
0.6452 Remote Similarity NPC472880
0.645 Remote Similarity NPC470205
0.645 Remote Similarity NPC470317
0.6446 Remote Similarity NPC471743
0.6444 Remote Similarity NPC113099
0.6443 Remote Similarity NPC469560
0.6429 Remote Similarity NPC283810
0.6429 Remote Similarity NPC134882
0.6423 Remote Similarity NPC1682
0.6423 Remote Similarity NPC188844
0.6423 Remote Similarity NPC59677
0.6423 Remote Similarity NPC155232
0.642 Remote Similarity NPC299582
0.6414 Remote Similarity NPC126458
0.6412 Remote Similarity NPC477003
0.6393 Remote Similarity NPC173413
0.6392 Remote Similarity NPC209362
0.6392 Remote Similarity NPC229055
0.6386 Remote Similarity NPC475594
0.638 Remote Similarity NPC279527
0.638 Remote Similarity NPC214960
0.638 Remote Similarity NPC182131
0.6379 Remote Similarity NPC71664
0.6379 Remote Similarity NPC476460
0.6376 Remote Similarity NPC287358
0.6375 Remote Similarity NPC474492
0.6371 Remote Similarity NPC238219
0.637 Remote Similarity NPC207428
0.6364 Remote Similarity NPC318183
0.6364 Remote Similarity NPC292265
0.6358 Remote Similarity NPC204867
0.6358 Remote Similarity NPC477998
0.6356 Remote Similarity NPC273758
0.6352 Remote Similarity NPC74357
0.6349 Remote Similarity NPC239185
0.6349 Remote Similarity NPC265220
0.6347 Remote Similarity NPC475607
0.6343 Remote Similarity NPC216550
0.6335 Remote Similarity NPC27904
0.6331 Remote Similarity NPC88110
0.6328 Remote Similarity NPC476993
0.6328 Remote Similarity NPC109514
0.6327 Remote Similarity NPC130655
0.6325 Remote Similarity NPC273033
0.6325 Remote Similarity NPC12936
0.632 Remote Similarity NPC260233
0.632 Remote Similarity NPC329430
0.6311 Remote Similarity NPC113307
0.631 Remote Similarity NPC237188
0.631 Remote Similarity NPC474081
0.6309 Remote Similarity NPC471123
0.6307 Remote Similarity NPC304203
0.6306 Remote Similarity NPC66936
0.6301 Remote Similarity NPC206186
0.6299 Remote Similarity NPC75724
0.6294 Remote Similarity NPC205946

  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 NPC192533 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
0.8092 Intermediate Similarity NPD2919 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD2918 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD2737 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD2331 Discontinued
0.7846 Intermediate Similarity NPD1640 Clinical (unspecified phase)
0.7842 Intermediate Similarity NPD6768 Approved
0.7823 Intermediate Similarity NPD1175 Approved
0.7778 Intermediate Similarity NPD1527 Phase 2
0.7778 Intermediate Similarity NPD1874 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD1626 Approved
0.7681 Intermediate Similarity NPD6342 Discontinued
0.7647 Intermediate Similarity NPD1541 Approved
0.763 Intermediate Similarity NPD1619 Phase 3
0.7606 Intermediate Similarity NPD5918 Discontinued
0.7535 Intermediate Similarity NPD1625 Approved
0.7517 Intermediate Similarity NPD4888 Discontinued
0.75 Intermediate Similarity NPD486 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD9541 Approved
0.7444 Intermediate Similarity NPD9539 Approved
0.7432 Intermediate Similarity NPD2790 Discontinued
0.7394 Intermediate Similarity NPD2010 Phase 3
0.7394 Intermediate Similarity NPD4461 Discontinued
0.7365 Intermediate Similarity NPD1854 Approved
0.7353 Intermediate Similarity NPD4549 Discontinued
0.7348 Intermediate Similarity NPD1079 Discontinued
0.7333 Intermediate Similarity NPD9540 Approved
0.7273 Intermediate Similarity NPD1222 Discontinued
0.7266 Intermediate Similarity NPD6740 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD5227 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6512 Approved
0.7222 Intermediate Similarity NPD6513 Approved
0.7218 Intermediate Similarity NPD1124 Approved
0.7218 Intermediate Similarity NPD1123 Approved
0.72 Intermediate Similarity NPD5086 Approved
0.7194 Intermediate Similarity NPD1919 Approved
0.7194 Intermediate Similarity NPD1920 Approved
0.7153 Intermediate Similarity NPD3434 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD2365 Approved
0.7103 Intermediate Similarity NPD1189 Approved
0.7055 Intermediate Similarity NPD4464 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2820 Phase 3
0.7042 Intermediate Similarity NPD1410 Phase 1
0.7039 Intermediate Similarity NPD4045 Phase 2
0.7039 Intermediate Similarity NPD4042 Phase 2
0.7029 Intermediate Similarity NPD1560 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD441 Approved
0.7021 Intermediate Similarity NPD2949 Approved
0.7021 Intermediate Similarity NPD2950 Approved
0.6986 Remote Similarity NPD6566 Discontinued
0.6986 Remote Similarity NPD3482 Approved
0.6978 Remote Similarity NPD1781 Discontinued
0.6963 Remote Similarity NPD3836 Clinical (unspecified phase)
0.6962 Remote Similarity NPD5921 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5932 Phase 3
0.6959 Remote Similarity NPD5931 Phase 3
0.6959 Remote Similarity NPD6017 Discontinued
0.6959 Remote Similarity NPD5933 Phase 3
0.6944 Remote Similarity NPD4077 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4161 Discontinued
0.6899 Remote Similarity NPD4645 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7254 Discontinued
0.6894 Remote Similarity NPD5466 Approved
0.6894 Remote Similarity NPD7662 Clinical (unspecified phase)
0.6892 Remote Similarity NPD3481 Approved
0.6892 Remote Similarity NPD4046 Approved
0.6892 Remote Similarity NPD4043 Approved
0.6887 Remote Similarity NPD5748 Phase 2
0.6884 Remote Similarity NPD1574 Approved
0.6883 Remote Similarity NPD6855 Clinical (unspecified phase)
0.687 Remote Similarity NPD5181 Approved
0.687 Remote Similarity NPD5180 Approved
0.687 Remote Similarity NPD5179 Approved
0.6867 Remote Similarity NPD7088 Discontinued
0.6866 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6866 Remote Similarity NPD922 Approved
0.6855 Remote Similarity NPD2413 Phase 2
0.6838 Remote Similarity NPD1517 Clinical (unspecified phase)
0.6835 Remote Similarity NPD1593 Approved
0.6835 Remote Similarity NPD5430 Discontinued
0.6832 Remote Similarity NPD7854 Phase 2
0.6829 Remote Similarity NPD2479 Phase 3
0.6829 Remote Similarity NPD2481 Approved
0.6828 Remote Similarity NPD6358 Phase 2
0.6818 Remote Similarity NPD2319 Discontinued
0.6818 Remote Similarity NPD7072 Phase 2
0.6815 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6806 Remote Similarity NPD1228 Phase 2
0.6806 Remote Similarity NPD2470 Clinical (unspecified phase)
0.68 Remote Similarity NPD1524 Phase 1
0.68 Remote Similarity NPD1956 Clinical (unspecified phase)
0.6795 Remote Similarity NPD4393 Approved
0.6795 Remote Similarity NPD33 Approved
0.6788 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6781 Remote Similarity NPD7142 Discontinued
0.677 Remote Similarity NPD3776 Discontinued
0.6761 Remote Similarity NPD2754 Discontinued
0.6759 Remote Similarity NPD1206 Approved
0.6759 Remote Similarity NPD1207 Approved
0.6748 Remote Similarity NPD1099 Approved
0.6748 Remote Similarity NPD1100 Approved
0.6732 Remote Similarity NPD1230 Approved
0.6728 Remote Similarity NPD5997 Discontinued
0.6719 Remote Similarity NPD990 Approved
0.6719 Remote Similarity NPD993 Approved
0.6719 Remote Similarity NPD1064 Approved
0.6719 Remote Similarity NPD1065 Approved
0.6715 Remote Similarity NPD678 Discontinued
0.6711 Remote Similarity NPD979 Approved
0.6711 Remote Similarity NPD5024 Approved
0.6711 Remote Similarity NPD7082 Approved
0.669 Remote Similarity NPD5131 Approved
0.6688 Remote Similarity NPD3248 Phase 1
0.6687 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2836 Approved
0.6667 Remote Similarity NPD5253 Approved
0.6667 Remote Similarity NPD1890 Clinical (unspecified phase)
0.6667 Remote Similarity NPD951 Approved
0.6667 Remote Similarity NPD7487 Discontinued
0.6667 Remote Similarity NPD5993 Phase 1
0.6667 Remote Similarity NPD2351 Discontinued
0.6667 Remote Similarity NPD6163 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7259 Approved
0.6646 Remote Similarity NPD4311 Approved
0.6645 Remote Similarity NPD7794 Clinical (unspecified phase)
0.6645 Remote Similarity NPD7612 Clinical (unspecified phase)
0.6643 Remote Similarity NPD1190 Approved
0.6643 Remote Similarity NPD4300 Clinical (unspecified phase)
0.6643 Remote Similarity NPD1482 Clinical (unspecified phase)
0.6642 Remote Similarity NPD5836 Discontinued
0.6623 Remote Similarity NPD7295 Approved
0.6622 Remote Similarity NPD1205 Approved
0.6622 Remote Similarity NPD1209 Approved
0.6621 Remote Similarity NPD5182 Approved
0.6621 Remote Similarity NPD5185 Approved
0.6621 Remote Similarity NPD5184 Approved
0.6617 Remote Similarity NPD3387 Approved
0.6606 Remote Similarity NPD3792 Approved
0.6606 Remote Similarity NPD3755 Clinical (unspecified phase)
0.6605 Remote Similarity NPD2369 Discontinued
0.6601 Remote Similarity NPD4942 Approved
0.6601 Remote Similarity NPD7528 Approved
0.6593 Remote Similarity NPD5162 Approved
0.6591 Remote Similarity NPD2039 Approved
0.6591 Remote Similarity NPD2038 Approved
0.6591 Remote Similarity NPD3001 Approved
0.6591 Remote Similarity NPD2999 Approved
0.6584 Remote Similarity NPD4643 Clinical (unspecified phase)
0.6567 Remote Similarity NPD1023 Approved
0.6567 Remote Similarity NPD1021 Approved
0.6567 Remote Similarity NPD1022 Approved
0.6567 Remote Similarity NPD1020 Approved
0.6564 Remote Similarity NPD5727 Clinical (unspecified phase)
0.6561 Remote Similarity NPD1208 Approved
0.6561 Remote Similarity NPD7091 Discontinued
0.6561 Remote Similarity NPD1211 Clinical (unspecified phase)
0.6555 Remote Similarity NPD650 Approved
0.6554 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6538 Remote Similarity NPD2360 Approved
0.6536 Remote Similarity NPD1802 Approved
0.6536 Remote Similarity NPD1801 Approved
0.6536 Remote Similarity NPD7478 Approved
0.6535 Remote Similarity NPD4734 Approved
0.6535 Remote Similarity NPD4735 Approved
0.6528 Remote Similarity NPD1070 Approved
0.6528 Remote Similarity NPD1069 Approved
0.6527 Remote Similarity NPD4330 Approved
0.6527 Remote Similarity NPD4329 Approved
0.6522 Remote Similarity NPD9272 Approved
0.6519 Remote Similarity NPD5660 Approved
0.6519 Remote Similarity NPD6018 Approved
0.6519 Remote Similarity NPD5659 Approved
0.6519 Remote Similarity NPD6019 Approved
0.6519 Remote Similarity NPD1323 Discontinued
0.6512 Remote Similarity NPD2197 Approved
0.6512 Remote Similarity NPD2192 Approved
0.6507 Remote Similarity NPD1531 Approved
0.6503 Remote Similarity NPD5186 Approved
0.6503 Remote Similarity NPD5183 Approved
0.6494 Remote Similarity NPD5942 Approved
0.6494 Remote Similarity NPD4939 Clinical (unspecified phase)
0.6494 Remote Similarity NPD5941 Approved
0.6493 Remote Similarity NPD2913 Approved
0.6493 Remote Similarity NPD2914 Approved
0.6486 Remote Similarity NPD5318 Discontinued
0.6486 Remote Similarity NPD7541 Clinical (unspecified phase)
0.6486 Remote Similarity NPD2670 Approved
0.6479 Remote Similarity NPD552 Approved
0.6479 Remote Similarity NPD553 Approved
0.6479 Remote Similarity NPD9567 Approved
0.6478 Remote Similarity NPD6629 Discontinued
0.6475 Remote Similarity NPD7609 Phase 3
0.6467 Remote Similarity NPD3782 Discontinued
0.6466 Remote Similarity NPD3865 Approved
0.6463 Remote Similarity NPD7663 Clinical (unspecified phase)
0.6456 Remote Similarity NPD7105 Phase 1
0.6454 Remote Similarity NPD3547 Approved
0.6454 Remote Similarity NPD3549 Approved
0.6454 Remote Similarity NPD3550 Clinical (unspecified phase)
0.6449 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3551 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