Structure

Physi-Chem Properties

Molecular Weight:  219.1
Volume:  249.528
LogP:  4.698
LogD:  3.976
LogS:  -5.955
# Rotatable Bonds:  2
TPSA:  12.03
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.665
Synthetic Accessibility Score:  1.395
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:  -4.39
MDCK Permeability:  1.3913531802245416e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.095
Human Intestinal Absorption (HIA):  0.061
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  0.743

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.506
Plasma Protein Binding (PPB):  98.30288696289062%
Volume Distribution (VD):  3.796
Pgp-substrate:  1.183295488357544%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.222
CYP2C19-inhibitor:  0.726
CYP2C19-substrate:  0.069
CYP2C9-inhibitor:  0.381
CYP2C9-substrate:  0.417
CYP2D6-inhibitor:  0.667
CYP2D6-substrate:  0.323
CYP3A4-inhibitor:  0.374
CYP3A4-substrate:  0.306

ADMET: Excretion

Clearance (CL):  7.769
Half-life (T1/2):  0.246

ADMET: Toxicity

hERG Blockers:  0.301
Human Hepatotoxicity (H-HT):  0.22
Drug-inuced Liver Injury (DILI):  0.95
AMES Toxicity:  0.589
Rat Oral Acute Toxicity:  0.149
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.96
Carcinogencity:  0.511
Eye Corrosion:  0.564
Eye Irritation:  0.984
Respiratory Toxicity:  0.297

Download Data

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

  Natural Product: NPC434

Natural Product ID:  NPC434
Common Name*:   N-Phenylnaphthalen-2-Amine
IUPAC Name:   N-phenylnaphthalen-2-amine
Synonyms:  
Standard InCHIKey:  KEQFTVQCIQJIQW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17H
SMILES:  c1ccc(cc1)Nc1ccc2c(c1)cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1543632
PubChem CID:   8679
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes

*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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO30807 Acroptilon repens Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[2348202]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Europe PMC[305622]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30807 Acroptilon repens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14276 Syngnathus acus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14276 Syngnathus acus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5502 Rhaponticum repens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30807 Acroptilon repens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14276 Syngnathus acus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5502 Rhaponticum repens Species Asteraceae 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
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[465793]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 12589.3 nM PMID[465793]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 12589.3 nM PMID[465793]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 39810.7 nM PMID[465793]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 25118.9 nM PMID[465793]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 20596.2 nM PMID[465794]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 316.2 nM PMID[465795]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 63095.7 nM PMID[465794]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 15848.9 nM PMID[465794]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 22387.2 nM PMID[465795]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 6309.6 nM PMID[465794]
NPT155 Individual Protein Aryl hydrocarbon receptor Homo sapiens Potency n.a. 50118.7 nM PMID[465795]
NPT155 Individual Protein Aryl hydrocarbon receptor Homo sapiens Potency n.a. 44668.4 nM PMID[465793]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 54482.7 nM PMID[465795]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 42163.2 nM PMID[465793]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[465794]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 15848.9 nM PMID[465794]
NPT158 Individual Protein Nuclear receptor subfamily 1 group I member 2 Rattus norvegicus Potency n.a. 44668.4 nM PMID[465795]
NPT158 Individual Protein Nuclear receptor subfamily 1 group I member 2 Rattus norvegicus Potency n.a. 44668.4 nM PMID[465793]
NPT159 Individual Protein Aberrant vpr protein Human immunodeficiency virus 1 Potency n.a. 17782.8 nM PMID[465794]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 2984.9 nM PMID[465793]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[465794]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 891.3 nM PMID[465794]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16360.1 nM PMID[465794]
NPT161 Individual Protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 8912.5 nM PMID[465794]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 8634.9 nM PMID[465795]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 16785.5 nM PMID[465793]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 6309.6 nM PMID[465793]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 54947.7 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 17228.9 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 43406.4 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 10804.4 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 21557.7 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 30637.9 nM PubChem BioAssay data set
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 48972.2 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 54947.7 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 54645.4 nM PubChem BioAssay data set
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 31622.8 nM PMID[465793]
NPT2 Others Unspecified Potency = 12589.3 nM PMID[465793]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 141.3 nM PMID[465794]
NPT98 Individual Protein HERG Homo sapiens Potency n.a. 25118.9 nM PMID[465793]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 56234.1 nM PMID[465794]
NPT2 Others Unspecified AbsAC40_uM n.a. 3.83 uM PMID[465794]
NPT2 Others Unspecified Potency n.a. 42163.2 nM PMID[465793]
NPT2 Others Unspecified Potency n.a. 37578.0 nM PMID[465793]
NPT610 Others Molecular identity unknown Potency n.a. 39810.7 nM PMID[465795]
NPT610 Others Molecular identity unknown Potency n.a. 31622.8 nM PMID[465793]
NPT2 Others Unspecified Potency n.a. 5623.4 nM PMID[465794]
NPT2 Others Unspecified Potency n.a. 68171.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30899.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9688.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19213.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 60757.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48702.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 13685.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8582.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9629.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54947.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30451 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34669.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54645.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5494.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3467 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54150.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34166.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76489.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 544.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43646.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 17123.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3045.1 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 43646.5 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 48702.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48972.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43406.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8634.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7695.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3890 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2713.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2730.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4826.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43277.1 nM PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC434 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
0.9604 High Similarity NPC79618
0.8317 Intermediate Similarity NPC108800
0.82 Intermediate Similarity NPC176858
0.8119 Intermediate Similarity NPC191444
0.798 Intermediate Similarity NPC229477
0.7951 Intermediate Similarity NPC328590
0.7928 Intermediate Similarity NPC302790
0.7573 Intermediate Similarity NPC30445
0.7545 Intermediate Similarity NPC291610
0.7521 Intermediate Similarity NPC475915
0.7339 Intermediate Similarity NPC192533
0.7333 Intermediate Similarity NPC173991
0.7315 Intermediate Similarity NPC329430
0.7293 Intermediate Similarity NPC312092
0.7238 Intermediate Similarity NPC111233
0.7209 Intermediate Similarity NPC282398
0.7207 Intermediate Similarity NPC323726
0.7099 Intermediate Similarity NPC473930
0.7087 Intermediate Similarity NPC134825
0.7049 Intermediate Similarity NPC313449
0.7048 Intermediate Similarity NPC258046
0.704 Intermediate Similarity NPC268534
0.7031 Intermediate Similarity NPC250361
0.7023 Intermediate Similarity NPC179365
0.7019 Intermediate Similarity NPC169016
0.7008 Intermediate Similarity NPC122718
0.6957 Remote Similarity NPC328877
0.6953 Remote Similarity NPC252794
0.6935 Remote Similarity NPC162689
0.6935 Remote Similarity NPC54102
0.693 Remote Similarity NPC239854
0.6923 Remote Similarity NPC473762
0.6894 Remote Similarity NPC475450
0.6885 Remote Similarity NPC288232
0.6881 Remote Similarity NPC470926
0.687 Remote Similarity NPC473587
0.686 Remote Similarity NPC296163
0.686 Remote Similarity NPC187036
0.686 Remote Similarity NPC314141
0.6838 Remote Similarity NPC169433
0.6822 Remote Similarity NPC262295
0.6818 Remote Similarity NPC475428
0.6809 Remote Similarity NPC477134
0.6774 Remote Similarity NPC192209
0.6769 Remote Similarity NPC145754
0.6746 Remote Similarity NPC279385
0.6746 Remote Similarity NPC179605
0.6719 Remote Similarity NPC41174
0.6713 Remote Similarity NPC33421
0.6693 Remote Similarity NPC215519
0.6693 Remote Similarity NPC103292
0.6667 Remote Similarity NPC226143
0.664 Remote Similarity NPC148140
0.6622 Remote Similarity NPC44773
0.6622 Remote Similarity NPC215584
0.6614 Remote Similarity NPC161052
0.6614 Remote Similarity NPC258787
0.6604 Remote Similarity NPC104070
0.6591 Remote Similarity NPC209389
0.6587 Remote Similarity NPC81561
0.6581 Remote Similarity NPC474430
0.6567 Remote Similarity NPC22079
0.6566 Remote Similarity NPC271732
0.6562 Remote Similarity NPC257490
0.656 Remote Similarity NPC313673
0.6522 Remote Similarity NPC314102
0.6522 Remote Similarity NPC251722
0.6512 Remote Similarity NPC132146
0.6486 Remote Similarity NPC78154
0.6471 Remote Similarity NPC301874
0.6458 Remote Similarity NPC109787
0.6449 Remote Similarity NPC119677
0.6443 Remote Similarity NPC206819
0.6443 Remote Similarity NPC41257
0.6443 Remote Similarity NPC56765
0.6443 Remote Similarity NPC318065
0.6442 Remote Similarity NPC12857
0.6419 Remote Similarity NPC184476
0.6418 Remote Similarity NPC473417
0.6418 Remote Similarity NPC9856
0.6406 Remote Similarity NPC143603
0.6389 Remote Similarity NPC133162
0.6383 Remote Similarity NPC284635
0.6377 Remote Similarity NPC198988
0.6376 Remote Similarity NPC286427
0.6346 Remote Similarity NPC98269
0.6346 Remote Similarity NPC325662
0.6333 Remote Similarity NPC474695
0.6331 Remote Similarity NPC325252
0.6328 Remote Similarity NPC320656
0.6328 Remote Similarity NPC264580
0.632 Remote Similarity NPC57051
0.6319 Remote Similarity NPC264589
0.6316 Remote Similarity NPC322040
0.6312 Remote Similarity NPC88097
0.6294 Remote Similarity NPC311330
0.6279 Remote Similarity NPC177684
0.6279 Remote Similarity NPC91958
0.6279 Remote Similarity NPC291962
0.6276 Remote Similarity NPC288838
0.6268 Remote Similarity NPC59084
0.6268 Remote Similarity NPC2949
0.6268 Remote Similarity NPC473429
0.6268 Remote Similarity NPC115611
0.6259 Remote Similarity NPC206592
0.625 Remote Similarity NPC139658
0.6233 Remote Similarity NPC21605
0.6232 Remote Similarity NPC313352
0.6231 Remote Similarity NPC258531
0.6231 Remote Similarity NPC112373
0.6231 Remote Similarity NPC161956
0.6224 Remote Similarity NPC63157
0.6224 Remote Similarity NPC473868
0.6214 Remote Similarity NPC29886
0.6214 Remote Similarity NPC218268
0.6214 Remote Similarity NPC261195
0.6214 Remote Similarity NPC96102
0.6212 Remote Similarity NPC254698
0.6209 Remote Similarity NPC90723
0.6209 Remote Similarity NPC162799
0.6198 Remote Similarity NPC313362
0.6197 Remote Similarity NPC2823
0.619 Remote Similarity NPC124005
0.6186 Remote Similarity NPC75496
0.6179 Remote Similarity NPC164802
0.6174 Remote Similarity NPC325903
0.617 Remote Similarity NPC125746
0.617 Remote Similarity NPC84911
0.617 Remote Similarity NPC105127
0.6165 Remote Similarity NPC46358
0.6159 Remote Similarity NPC82295
0.6159 Remote Similarity NPC216643
0.6154 Remote Similarity NPC469784
0.6154 Remote Similarity NPC469761
0.6154 Remote Similarity NPC194411
0.6154 Remote Similarity NPC469767
0.6154 Remote Similarity NPC469779
0.6154 Remote Similarity NPC469768
0.6154 Remote Similarity NPC469780
0.6154 Remote Similarity NPC469783
0.6154 Remote Similarity NPC98976
0.6149 Remote Similarity NPC53947
0.6148 Remote Similarity NPC476950
0.6148 Remote Similarity NPC476140
0.6148 Remote Similarity NPC469949
0.6138 Remote Similarity NPC242556
0.6136 Remote Similarity NPC39818
0.6127 Remote Similarity NPC130251
0.6116 Remote Similarity NPC38262
0.6111 Remote Similarity NPC469766
0.6107 Remote Similarity NPC470233
0.6102 Remote Similarity NPC317642
0.6098 Remote Similarity NPC172170
0.6096 Remote Similarity NPC469735
0.6095 Remote Similarity NPC271642
0.6093 Remote Similarity NPC51054
0.609 Remote Similarity NPC473484
0.6087 Remote Similarity NPC53044
0.6084 Remote Similarity NPC73767
0.6084 Remote Similarity NPC301760
0.6084 Remote Similarity NPC110126
0.6078 Remote Similarity NPC72670
0.6078 Remote Similarity NPC219246
0.6078 Remote Similarity NPC229235
0.6074 Remote Similarity NPC146373
0.6074 Remote Similarity NPC245244
0.6074 Remote Similarity NPC166424
0.6071 Remote Similarity NPC60408
0.6067 Remote Similarity NPC200743
0.6061 Remote Similarity NPC291066
0.6058 Remote Similarity NPC96835
0.6058 Remote Similarity NPC112609
0.6058 Remote Similarity NPC194562
0.6058 Remote Similarity NPC66775
0.6058 Remote Similarity NPC113000
0.6058 Remote Similarity NPC258492
0.6058 Remote Similarity NPC122327
0.6058 Remote Similarity NPC472245
0.6054 Remote Similarity NPC469740
0.6054 Remote Similarity NPC63545
0.6054 Remote Similarity NPC129042
0.6053 Remote Similarity NPC76982
0.6051 Remote Similarity NPC280548
0.6047 Remote Similarity NPC125416
0.6043 Remote Similarity NPC101165
0.6042 Remote Similarity NPC279081
0.6038 Remote Similarity NPC275305
0.6038 Remote Similarity NPC37423
0.6026 Remote Similarity NPC38736
0.6026 Remote Similarity NPC476219
0.6016 Remote Similarity NPC473498
0.6016 Remote Similarity NPC205652
0.6014 Remote Similarity NPC201380
0.6014 Remote Similarity NPC469811
0.6014 Remote Similarity NPC179787
0.6013 Remote Similarity NPC201634
0.6013 Remote Similarity NPC474880
0.6013 Remote Similarity NPC6436
0.6013 Remote Similarity NPC475990
0.6013 Remote Similarity NPC221786

  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 NPC434 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
0.7876 Intermediate Similarity NPD2039 Approved
0.7876 Intermediate Similarity NPD2038 Approved
0.787 Intermediate Similarity NPD4734 Approved
0.787 Intermediate Similarity NPD4735 Approved
0.7719 Intermediate Similarity NPD2999 Approved
0.7719 Intermediate Similarity NPD3001 Approved
0.7679 Intermediate Similarity NPD5253 Approved
0.7589 Intermediate Similarity NPD990 Approved
0.7589 Intermediate Similarity NPD993 Approved
0.7544 Intermediate Similarity NPD4116 Approved
0.7544 Intermediate Similarity NPD7633 Discontinued
0.7522 Intermediate Similarity NPD6300 Approved
0.7522 Intermediate Similarity NPD6299 Approved
0.7436 Intermediate Similarity NPD2913 Approved
0.7436 Intermediate Similarity NPD2914 Approved
0.7434 Intermediate Similarity NPD3545 Approved
0.7434 Intermediate Similarity NPD3546 Approved
0.7373 Intermediate Similarity NPD5629 Discontinued
0.7368 Intermediate Similarity NPD4114 Approved
0.7368 Intermediate Similarity NPD4115 Approved
0.7315 Intermediate Similarity NPD5554 Approved
0.7257 Intermediate Similarity NPD4937 Approved
0.7257 Intermediate Similarity NPD4936 Approved
0.7248 Intermediate Similarity NPD2005 Discontinued
0.7241 Intermediate Similarity NPD1539 Approved
0.7222 Intermediate Similarity NPD3240 Phase 2
0.72 Intermediate Similarity NPD2938 Approved
0.72 Intermediate Similarity NPD2940 Approved
0.713 Intermediate Similarity NPD4408 Approved
0.713 Intermediate Similarity NPD4407 Approved
0.713 Intermediate Similarity NPD4405 Approved
0.7107 Intermediate Similarity NPD2464 Approved
0.7107 Intermediate Similarity NPD2463 Approved
0.7107 Intermediate Similarity NPD2467 Approved
0.7087 Intermediate Similarity NPD1949 Approved
0.7087 Intermediate Similarity NPD1950 Approved
0.7054 Intermediate Similarity NPD1946 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD7481 Approved
0.7049 Intermediate Similarity NPD7480 Approved
0.7049 Intermediate Similarity NPD299 Phase 3
0.7008 Intermediate Similarity NPD4985 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5180 Approved
0.7 Intermediate Similarity NPD5181 Approved
0.7 Intermediate Similarity NPD5179 Approved
0.7 Intermediate Similarity NPD947 Approved
0.6991 Remote Similarity NPD1916 Discontinued
0.6985 Remote Similarity NPD6768 Approved
0.6944 Remote Similarity NPD5915 Approved
0.6935 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2918 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2919 Clinical (unspecified phase)
0.6899 Remote Similarity NPD1560 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5598 Approved
0.6875 Remote Similarity NPD6320 Approved
0.6875 Remote Similarity NPD5597 Approved
0.6835 Remote Similarity NPD5254 Discontinued
0.6822 Remote Similarity NPD6900 Discontinued
0.6809 Remote Similarity NPD4888 Discontinued
0.6797 Remote Similarity NPD1640 Clinical (unspecified phase)
0.6794 Remote Similarity NPD4019 Clinical (unspecified phase)
0.6794 Remote Similarity NPD8263 Discontinued
0.6792 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6765 Remote Similarity NPD1626 Approved
0.6765 Remote Similarity NPD1262 Discovery
0.6748 Remote Similarity NPD1723 Phase 2
0.6748 Remote Similarity NPD1720 Phase 2
0.6742 Remote Similarity NPD4300 Clinical (unspecified phase)
0.6741 Remote Similarity NPD4880 Discontinued
0.6739 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6723 Remote Similarity NPD1721 Clinical (unspecified phase)
0.672 Remote Similarity NPD5657 Phase 3
0.672 Remote Similarity NPD922 Approved
0.6714 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6698 Remote Similarity NPD2538 Approved
0.6698 Remote Similarity NPD2539 Approved
0.6691 Remote Similarity NPD1253 Approved
0.6691 Remote Similarity NPD1255 Approved
0.6691 Remote Similarity NPD1256 Approved
0.6691 Remote Similarity NPD1254 Approved
0.6667 Remote Similarity NPD5518 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3498 Approved
0.6667 Remote Similarity NPD3548 Approved
0.6667 Remote Similarity NPD3499 Approved
0.6667 Remote Similarity NPD2010 Phase 3
0.6667 Remote Similarity NPD2871 Approved
0.6667 Remote Similarity NPD2870 Approved
0.664 Remote Similarity NPD153 Clinical (unspecified phase)
0.6621 Remote Similarity NPD5086 Approved
0.6617 Remote Similarity NPD3841 Phase 3
0.6617 Remote Similarity NPD4867 Approved
0.6617 Remote Similarity NPD4866 Approved
0.6615 Remote Similarity NPD8128 Discontinued
0.6607 Remote Similarity NPD6548 Approved
0.6607 Remote Similarity NPD6549 Approved
0.6607 Remote Similarity NPD4545 Approved
0.6607 Remote Similarity NPD735 Approved
0.6607 Remote Similarity NPD736 Approved
0.6607 Remote Similarity NPD4542 Approved
0.6591 Remote Similarity NPD7582 Discontinued
0.6591 Remote Similarity NPD3011 Approved
0.6591 Remote Similarity NPD3012 Approved
0.6591 Remote Similarity NPD3008 Approved
0.6587 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6585 Remote Similarity NPD1175 Approved
0.6575 Remote Similarity NPD5606 Discontinued
0.6571 Remote Similarity NPD1625 Approved
0.6569 Remote Similarity NPD6342 Discontinued
0.6565 Remote Similarity NPD3438 Approved
0.6565 Remote Similarity NPD2840 Approved
0.6565 Remote Similarity NPD1836 Discontinued
0.656 Remote Similarity NPD6069 Approved
0.656 Remote Similarity NPD6070 Approved
0.6555 Remote Similarity NPD1065 Approved
0.6555 Remote Similarity NPD1064 Approved
0.6547 Remote Similarity NPD1953 Discontinued
0.6545 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6544 Remote Similarity NPD2331 Discontinued
0.6541 Remote Similarity NPD3424 Clinical (unspecified phase)
0.6533 Remote Similarity NPD3323 Discontinued
0.6531 Remote Similarity NPD2748 Clinical (unspecified phase)
0.6525 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6506 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1251 Discontinued
0.6514 Remote Similarity NPD4146 Approved
0.6514 Remote Similarity NPD3428 Approved
0.6514 Remote Similarity NPD4145 Approved
0.6514 Remote Similarity NPD3426 Approved
0.6513 Remote Similarity NPD5021 Discontinued
0.6503 Remote Similarity NPD1683 Approved
0.6496 Remote Similarity NPD1515 Discontinued
0.6493 Remote Similarity NPD1619 Phase 3
0.6484 Remote Similarity NPD6892 Discontinued
0.6483 Remote Similarity NPD8353 Approved
0.6483 Remote Similarity NPD8355 Approved
0.6479 Remote Similarity NPD6622 Phase 1
0.6475 Remote Similarity NPD6606 Clinical (unspecified phase)
0.6466 Remote Similarity NPD2036 Approved
0.646 Remote Similarity NPD3982 Approved
0.646 Remote Similarity NPD2878 Approved
0.646 Remote Similarity NPD3980 Approved
0.6457 Remote Similarity NPD5511 Discontinued
0.6455 Remote Similarity NPD3345 Approved
0.6446 Remote Similarity NPD8010 Approved
0.6446 Remote Similarity NPD8009 Approved
0.6439 Remote Similarity NPD572 Clinical (unspecified phase)
0.6434 Remote Similarity NPD1517 Clinical (unspecified phase)
0.6434 Remote Similarity NPD678 Discontinued
0.6429 Remote Similarity NPD3000 Approved
0.6429 Remote Similarity NPD2997 Approved
0.6429 Remote Similarity NPD2998 Approved
0.6429 Remote Similarity NPD4543 Discontinued
0.6424 Remote Similarity NPD3583 Phase 2
0.6423 Remote Similarity NPD3385 Approved
0.6418 Remote Similarity NPD4490 Approved
0.6418 Remote Similarity NPD4489 Approved
0.6417 Remote Similarity NPD7170 Discontinued
0.6403 Remote Similarity NPD6554 Approved
0.6403 Remote Similarity NPD45 Approved
0.64 Remote Similarity NPD1813 Discontinued
0.64 Remote Similarity NPD5631 Phase 3
0.6397 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6395 Remote Similarity NPD8354 Approved
0.6393 Remote Similarity NPD1107 Approved
0.6393 Remote Similarity NPD1108 Approved
0.6389 Remote Similarity NPD3427 Approved
0.6389 Remote Similarity NPD3429 Approved
0.6389 Remote Similarity NPD7794 Clinical (unspecified phase)
0.6379 Remote Similarity NPD6498 Approved
0.6379 Remote Similarity NPD6499 Approved
0.6379 Remote Similarity NPD5832 Phase 3
0.637 Remote Similarity NPD6489 Phase 3
0.6364 Remote Similarity NPD5060 Phase 1
0.6364 Remote Similarity NPD3301 Approved
0.6364 Remote Similarity NPD5136 Clinical (unspecified phase)
0.6357 Remote Similarity NPD3957 Phase 2
0.6357 Remote Similarity NPD4416 Clinical (unspecified phase)
0.6357 Remote Similarity NPD6522 Clinical (unspecified phase)
0.6357 Remote Similarity NPD3956 Phase 3
0.6357 Remote Similarity NPD3955 Approved
0.6351 Remote Similarity NPD976 Approved
0.6351 Remote Similarity NPD975 Approved
0.6351 Remote Similarity NPD977 Approved
0.635 Remote Similarity NPD7200 Approved
0.6343 Remote Similarity NPD4549 Discontinued
0.6343 Remote Similarity NPD995 Clinical (unspecified phase)
0.6338 Remote Similarity NPD5053 Discontinued
0.6336 Remote Similarity NPD1561 Phase 2
0.6333 Remote Similarity NPD233 Clinical (unspecified phase)
0.6331 Remote Similarity NPD3864 Clinical (unspecified phase)
0.6331 Remote Similarity NPD6358 Phase 2
0.6328 Remote Similarity NPD2396 Approved
0.6328 Remote Similarity NPD2395 Approved
0.6328 Remote Similarity NPD1216 Clinical (unspecified phase)
0.6324 Remote Similarity NPD6822 Approved
0.6324 Remote Similarity NPD6820 Approved
0.6323 Remote Similarity NPD3776 Discontinued
0.6321 Remote Similarity NPD5372 Approved
0.6321 Remote Similarity NPD5371 Approved
0.6319 Remote Similarity NPD5839 Clinical (unspecified phase)
0.6316 Remote Similarity NPD243 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