Structure

Physi-Chem Properties

Molecular Weight:  232.1
Volume:  251.968
LogP:  4.426
LogD:  4.035
LogS:  -6.067
# Rotatable Bonds:  0
TPSA:  17.82
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  1.997
Fsp3:  0.062
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:  -4.789
MDCK Permeability:  2.2120515495771542e-05
Pgp-inhibitor:  0.037
Pgp-substrate:  0.029
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.9
30% Bioavailability (F30%):  0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.926
Plasma Protein Binding (PPB):  97.3289794921875%
Volume Distribution (VD):  1.093
Pgp-substrate:  1.1146180629730225%

ADMET: Metabolism

CYP1A2-inhibitor:  0.991
CYP1A2-substrate:  0.507
CYP2C19-inhibitor:  0.662
CYP2C19-substrate:  0.129
CYP2C9-inhibitor:  0.457
CYP2C9-substrate:  0.789
CYP2D6-inhibitor:  0.169
CYP2D6-substrate:  0.885
CYP3A4-inhibitor:  0.209
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  6.066
Half-life (T1/2):  0.132

ADMET: Toxicity

hERG Blockers:  0.044
Human Hepatotoxicity (H-HT):  0.184
Drug-inuced Liver Injury (DILI):  0.483
AMES Toxicity:  0.917
Rat Oral Acute Toxicity:  0.291
Maximum Recommended Daily Dose:  0.898
Skin Sensitization:  0.151
Carcinogencity:  0.84
Eye Corrosion:  0.006
Eye Irritation:  0.978
Respiratory Toxicity:  0.354

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

  Natural Product: NPC296163

Natural Product ID:  NPC296163
Common Name*:   Cryptolepine
IUPAC Name:   5-methylindolo[3,2-b]quinoline
Synonyms:   Cryptolepine
Standard InCHIKey:  KURWKDDWCJELSV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12N2/c1-18-15-9-5-2-6-11(15)10-14-16(18)12-7-3-4-8-13(12)17-14/h2-10H,1H3
SMILES:  Cn1c2ccccc2cc2c1c1ccccc1n2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL119096
PubChem CID:   82143
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000061] Indoloquinolines

*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
NPO40885 Microphilis guyanensis Species n.a. n.a. n.a. n.a. n.a. PMID[10425120]
NPO17824 Genipa americana Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[10425120]
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. n.a. n.a. PMID[14640526]
NPO17824 Genipa americana Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[1667413]
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. depth of 25 m off the shore of Keomun Island, Korea 2004-AUG PMID[18407691]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO20912 Wisteria brachybotrys Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[2853205]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32998509]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[9249972]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[9667966]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17824 Genipa americana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17824 Genipa americana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17131 Yucca periculosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20299 Strongylophora durissima n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18755 Fumaria judaica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20169 Alseodaphne perakensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20989 Calea integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21890 Epidendrum moseni Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17824 Genipa americana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20912 Wisteria brachybotrys Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20237 Poecillastra wondoensis Species Vulcanellidae 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
NPT520 Cell Line 3T3-L1 Mus musculus Change of predose = -19.7 % PMID[525308]
NPT520 Cell Line 3T3-L1 Mus musculus Change of predose = -30.0 % PMID[525308]
NPT171 Cell Line MRC5 Homo sapiens IC50 = 1500.0 nM PMID[525309]
NPT189 Cell Line Vero Chlorocebus aethiops TC50 = 3.2 ug ml-1 PMID[525317]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 3.2 ug.mL-1 PMID[525318]
NPT144 Individual Protein Telomerase reverse transcriptase Homo sapiens IC50 = 9400.0 nM PMID[525319]
NPT189 Cell Line Vero Chlorocebus aethiops Activity = 8.88 uM PMID[525320]
NPT189 Cell Line Vero Chlorocebus aethiops TC50 = 3.2 ug ml-1 PMID[525321]
NPT144 Individual Protein Telomerase reverse transcriptase Homo sapiens IC50 = 9400.0 nM PMID[525322]
NPT32 Organism Mus musculus Mus musculus Mean body weight = 39.4 g mouse-1 PMID[525308]
NPT32 Organism Mus musculus Mus musculus Mean body weight = 38.7 g mouse-1 PMID[525308]
NPT32 Organism Mus musculus Mus musculus Food intake = 1.0 g mouse-1 day-1 PMID[525308]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2300.0 nM PMID[525309]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2000.0 nM PMID[525309]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 3000.0 nM PMID[525309]
NPT317 Uncleic Acid Nucleic Acid IC50 = 65700.0 nM PMID[525309]
NPT27 Others Unspecified IC50 = 1500.0 nM PMID[525310]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.027 ug.mL-1 PMID[525312]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.041 ug.mL-1 PMID[525312]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.033 ug.mL-1 PMID[525312]
NPT475 Organism Plasmodium yoelii Plasmodium yoelii Activity = 13.7 % PMID[525312]
NPT474 Organism Plasmodium berghei Plasmodium berghei Activity = 45.4 % PMID[525312]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 0.5 ug ml-1 PMID[525313]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 230.0 nM PMID[525315]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2000.0 nM PMID[525316]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 3000.0 nM PMID[525316]
NPT20 Organism Candida albicans Candida albicans IC50 = 20.0 ug.mL-1 PMID[525317]
NPT20 Organism Candida albicans Candida albicans MIC > 20.0 ug.mL-1 PMID[525317]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 20.0 ug.mL-1 PMID[525317]
NPT20 Organism Candida albicans Candida albicans MIC = 12.5 ug.mL-1 PMID[525317]
NPT20 Organism Candida albicans Candida albicans MIC = 250.0 ug.mL-1 PMID[525317]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 12.5 ug.mL-1 PMID[525318]
NPT20 Organism Candida albicans Candida albicans IC50 = 250.0 ug.mL-1 PMID[525318]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 43251.38 nM PMID[525320]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 43300.0 nM PMID[525320]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC > 25.0 ug ml-1 PMID[525321]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 12.5 ug.mL-1 PMID[525321]
NPT20 Organism Candida albicans Candida albicans MIC = 250.0 ug.mL-1 PMID[525321]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 29.0 % PMID[525321]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae FC = 1.7 n.a. PMID[525321]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae FC = 3.5 n.a. PMID[525321]
NPT2 Others Unspecified Selectivity Index < 0.13 n.a. PMID[525321]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 1600.0 nM PMID[525323]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.027 ug.mL-1 PMID[525324]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.027 ug.mL-1 PMID[525324]

☑ 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 NPC296163 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
0.9633 High Similarity NPC192209
0.9266 High Similarity NPC187036
0.8929 High Similarity NPC288232
0.8678 High Similarity NPC9856
0.8609 High Similarity NPC313449
0.84 Intermediate Similarity NPC184437
0.8065 Intermediate Similarity NPC476950
0.7982 Intermediate Similarity NPC302790
0.7928 Intermediate Similarity NPC291610
0.7826 Intermediate Similarity NPC164802
0.7797 Intermediate Similarity NPC314141
0.7769 Intermediate Similarity NPC264580
0.7612 Intermediate Similarity NPC471574
0.7445 Intermediate Similarity NPC136002
0.7445 Intermediate Similarity NPC20144
0.7419 Intermediate Similarity NPC54102
0.7419 Intermediate Similarity NPC162689
0.7398 Intermediate Similarity NPC148140
0.7344 Intermediate Similarity NPC122718
0.7339 Intermediate Similarity NPC81561
0.7339 Intermediate Similarity NPC476160
0.7313 Intermediate Similarity NPC325599
0.7313 Intermediate Similarity NPC198988
0.7302 Intermediate Similarity NPC475915
0.7273 Intermediate Similarity NPC22079
0.7273 Intermediate Similarity NPC53044
0.7239 Intermediate Similarity NPC300299
0.7231 Intermediate Similarity NPC478079
0.7214 Intermediate Similarity NPC469525
0.7206 Intermediate Similarity NPC314102
0.7206 Intermediate Similarity NPC251722
0.7203 Intermediate Similarity NPC117032
0.7182 Intermediate Similarity NPC78154
0.7174 Intermediate Similarity NPC238499
0.7165 Intermediate Similarity NPC257490
0.7165 Intermediate Similarity NPC215519
0.7143 Intermediate Similarity NPC79618
0.7132 Intermediate Similarity NPC325252
0.7101 Intermediate Similarity NPC88097
0.7092 Intermediate Similarity NPC469735
0.7054 Intermediate Similarity NPC41174
0.7042 Intermediate Similarity NPC469740
0.7 Intermediate Similarity NPC46358
0.6978 Remote Similarity NPC104483
0.697 Remote Similarity NPC250361
0.6963 Remote Similarity NPC475450
0.6959 Remote Similarity NPC475990
0.6957 Remote Similarity NPC150259
0.6957 Remote Similarity NPC125746
0.694 Remote Similarity NPC473587
0.6929 Remote Similarity NPC2949
0.6929 Remote Similarity NPC59084
0.6923 Remote Similarity NPC328683
0.6923 Remote Similarity NPC478186
0.6923 Remote Similarity NPC283130
0.6918 Remote Similarity NPC281094
0.6912 Remote Similarity NPC473930
0.6905 Remote Similarity NPC147957
0.6897 Remote Similarity NPC40070
0.6889 Remote Similarity NPC476689
0.6889 Remote Similarity NPC476687
0.6889 Remote Similarity NPC475428
0.6889 Remote Similarity NPC476685
0.6884 Remote Similarity NPC218268
0.6879 Remote Similarity NPC63157
0.6879 Remote Similarity NPC277157
0.6879 Remote Similarity NPC473868
0.6875 Remote Similarity NPC291962
0.6875 Remote Similarity NPC177684
0.6867 Remote Similarity NPC476231
0.6866 Remote Similarity NPC473762
0.686 Remote Similarity NPC434
0.6857 Remote Similarity NPC2823
0.6853 Remote Similarity NPC470440
0.6842 Remote Similarity NPC476140
0.6838 Remote Similarity NPC179365
0.6825 Remote Similarity NPC143156
0.6824 Remote Similarity NPC51054
0.6822 Remote Similarity NPC161956
0.6822 Remote Similarity NPC112373
0.6822 Remote Similarity NPC258531
0.6809 Remote Similarity NPC115611
0.6809 Remote Similarity NPC284635
0.6807 Remote Similarity NPC178681
0.6781 Remote Similarity NPC206592
0.6781 Remote Similarity NPC33421
0.6767 Remote Similarity NPC252794
0.6759 Remote Similarity NPC21605
0.6757 Remote Similarity NPC476219
0.6738 Remote Similarity NPC110126
0.6738 Remote Similarity NPC73767
0.6733 Remote Similarity NPC318065
0.6733 Remote Similarity NPC206819
0.6733 Remote Similarity NPC474880
0.6733 Remote Similarity NPC221786
0.6727 Remote Similarity NPC229477
0.6718 Remote Similarity NPC48564
0.6718 Remote Similarity NPC265605
0.6718 Remote Similarity NPC182570
0.6716 Remote Similarity NPC469949
0.6716 Remote Similarity NPC145754
0.6714 Remote Similarity NPC83214
0.6714 Remote Similarity NPC84911
0.6711 Remote Similarity NPC478182
0.6692 Remote Similarity NPC317564
0.669 Remote Similarity NPC469761
0.669 Remote Similarity NPC469767
0.669 Remote Similarity NPC469780
0.669 Remote Similarity NPC469768
0.669 Remote Similarity NPC469784
0.669 Remote Similarity NPC469783
0.669 Remote Similarity NPC469779
0.6689 Remote Similarity NPC229173
0.6689 Remote Similarity NPC325903
0.6667 Remote Similarity NPC243162
0.6667 Remote Similarity NPC242556
0.6667 Remote Similarity NPC169433
0.6644 Remote Similarity NPC201380
0.6644 Remote Similarity NPC179787
0.6644 Remote Similarity NPC476297
0.6644 Remote Similarity NPC470111
0.6643 Remote Similarity NPC261195
0.6643 Remote Similarity NPC96102
0.6643 Remote Similarity NPC29886
0.6643 Remote Similarity NPC469766
0.6641 Remote Similarity NPC313673
0.6623 Remote Similarity NPC293487
0.6621 Remote Similarity NPC204141
0.662 Remote Similarity NPC312092
0.6618 Remote Similarity NPC473417
0.6618 Remote Similarity NPC226662
0.6615 Remote Similarity NPC226143
0.6615 Remote Similarity NPC91958
0.6609 Remote Similarity NPC108800
0.6607 Remote Similarity NPC262295
0.6601 Remote Similarity NPC469541
0.6599 Remote Similarity NPC37548
0.6599 Remote Similarity NPC321911
0.6596 Remote Similarity NPC105127
0.6594 Remote Similarity NPC82295
0.6589 Remote Similarity NPC476566
0.6585 Remote Similarity NPC20322
0.6579 Remote Similarity NPC81229
0.6579 Remote Similarity NPC191444
0.6579 Remote Similarity NPC255229
0.6575 Remote Similarity NPC143872
0.6575 Remote Similarity NPC63545
0.6575 Remote Similarity NPC288838
0.6567 Remote Similarity NPC476322
0.6558 Remote Similarity NPC2165
0.6558 Remote Similarity NPC195507
0.6556 Remote Similarity NPC104345
0.6555 Remote Similarity NPC75496
0.6555 Remote Similarity NPC213774
0.6554 Remote Similarity NPC53947
0.6549 Remote Similarity NPC207554
0.6549 Remote Similarity NPC111233
0.6545 Remote Similarity NPC134825
0.6538 Remote Similarity NPC297486
0.6538 Remote Similarity NPC65080
0.6538 Remote Similarity NPC471402
0.6538 Remote Similarity NPC240136
0.6536 Remote Similarity NPC194881
0.6531 Remote Similarity NPC469811
0.6531 Remote Similarity NPC477134
0.6522 Remote Similarity NPC282398
0.6522 Remote Similarity NPC470926
0.6522 Remote Similarity NPC207428
0.6516 Remote Similarity NPC478183
0.6513 Remote Similarity NPC6436
0.6513 Remote Similarity NPC56765
0.6508 Remote Similarity NPC27802
0.6503 Remote Similarity NPC316811
0.6503 Remote Similarity NPC32002
0.6503 Remote Similarity NPC315348
0.65 Remote Similarity NPC326792
0.6494 Remote Similarity NPC478184
0.6494 Remote Similarity NPC21174
0.6494 Remote Similarity NPC271797
0.6491 Remote Similarity NPC176858
0.6489 Remote Similarity NPC143603
0.6486 Remote Similarity NPC187951
0.6486 Remote Similarity NPC124005
0.6484 Remote Similarity NPC205652
0.6484 Remote Similarity NPC470550
0.6483 Remote Similarity NPC190296
0.6475 Remote Similarity NPC101165
0.6471 Remote Similarity NPC122141
0.6467 Remote Similarity NPC471132
0.6463 Remote Similarity NPC254798
0.6458 Remote Similarity NPC279081
0.6452 Remote Similarity NPC471130
0.6449 Remote Similarity NPC476131
0.6447 Remote Similarity NPC286427
0.6447 Remote Similarity NPC299594
0.6443 Remote Similarity NPC148592
0.6439 Remote Similarity NPC179605
0.6439 Remote Similarity NPC279385
0.6438 Remote Similarity NPC116519
0.6433 Remote Similarity NPC474897

  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 NPC296163 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
0.8609 High Similarity NPD7481 Approved
0.8609 High Similarity NPD7480 Approved
0.8378 Intermediate Similarity NPD6300 Approved
0.8378 Intermediate Similarity NPD6299 Approved
0.8197 Intermediate Similarity NPD4985 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD993 Approved
0.8125 Intermediate Similarity NPD990 Approved
0.8051 Intermediate Similarity NPD2464 Approved
0.8051 Intermediate Similarity NPD2463 Approved
0.8051 Intermediate Similarity NPD2467 Approved
0.7984 Intermediate Similarity NPD2840 Approved
0.7903 Intermediate Similarity NPD1937 Approved
0.7826 Intermediate Similarity NPD477 Phase 1
0.7807 Intermediate Similarity NPD3545 Approved
0.7807 Intermediate Similarity NPD3546 Approved
0.7797 Intermediate Similarity NPD2913 Approved
0.7797 Intermediate Similarity NPD2914 Approved
0.7759 Intermediate Similarity NPD4116 Approved
0.7739 Intermediate Similarity NPD4115 Approved
0.7739 Intermediate Similarity NPD4114 Approved
0.7642 Intermediate Similarity NPD2340 Discontinued
0.7586 Intermediate Similarity NPD5253 Approved
0.7583 Intermediate Similarity NPD5631 Phase 3
0.75 Intermediate Similarity NPD6301 Phase 2
0.75 Intermediate Similarity NPD3385 Approved
0.7479 Intermediate Similarity NPD2999 Approved
0.7479 Intermediate Similarity NPD3001 Approved
0.7458 Intermediate Similarity NPD7633 Discontinued
0.7456 Intermediate Similarity NPD4734 Approved
0.7456 Intermediate Similarity NPD4735 Approved
0.7445 Intermediate Similarity NPD4047 Discontinued
0.7438 Intermediate Similarity NPD5629 Discontinued
0.7385 Intermediate Similarity NPD4019 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD5657 Phase 3
0.7333 Intermediate Similarity NPD45 Approved
0.7333 Intermediate Similarity NPD6554 Approved
0.7328 Intermediate Similarity NPD3654 Approved
0.7319 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6070 Approved
0.7317 Intermediate Similarity NPD6069 Approved
0.7313 Intermediate Similarity NPD1883 Approved
0.7227 Intermediate Similarity NPD1721 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5179 Approved
0.7213 Intermediate Similarity NPD5181 Approved
0.7213 Intermediate Similarity NPD5180 Approved
0.7209 Intermediate Similarity NPD2143 Discontinued
0.7203 Intermediate Similarity NPD3248 Phase 1
0.7197 Intermediate Similarity NPD4300 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2038 Approved
0.719 Intermediate Similarity NPD2039 Approved
0.7185 Intermediate Similarity NPD2292 Approved
0.7179 Intermediate Similarity NPD1728 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD1539 Approved
0.7153 Intermediate Similarity NPD1870 Approved
0.7153 Intermediate Similarity NPD1866 Approved
0.7153 Intermediate Similarity NPD1864 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2212 Approved
0.7143 Intermediate Similarity NPD2210 Approved
0.7132 Intermediate Similarity NPD1255 Approved
0.7132 Intermediate Similarity NPD1254 Approved
0.7132 Intermediate Similarity NPD1253 Approved
0.7132 Intermediate Similarity NPD1256 Approved
0.7103 Intermediate Similarity NPD6285 Phase 2
0.7101 Intermediate Similarity NPD4451 Approved
0.7101 Intermediate Similarity NPD4450 Approved
0.7094 Intermediate Similarity NPD2244 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2679 Approved
0.7083 Intermediate Similarity NPD2678 Approved
0.708 Intermediate Similarity NPD2733 Approved
0.7071 Intermediate Similarity NPD6506 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD3841 Phase 3
0.7068 Intermediate Similarity NPD4867 Approved
0.7068 Intermediate Similarity NPD4866 Approved
0.7059 Intermediate Similarity NPD1065 Approved
0.7059 Intermediate Similarity NPD1998 Approved
0.7059 Intermediate Similarity NPD1064 Approved
0.7054 Intermediate Similarity NPD1561 Phase 2
0.705 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD2118 Approved
0.7045 Intermediate Similarity NPD2119 Approved
0.7042 Intermediate Similarity NPD1683 Approved
0.7029 Intermediate Similarity NPD2304 Approved
0.7029 Intermediate Similarity NPD3276 Approved
0.7025 Intermediate Similarity NPD1107 Approved
0.7025 Intermediate Similarity NPD3548 Approved
0.7025 Intermediate Similarity NPD1108 Approved
0.7023 Intermediate Similarity NPD1950 Approved
0.7023 Intermediate Similarity NPD1949 Approved
0.7015 Intermediate Similarity NPD6820 Approved
0.7015 Intermediate Similarity NPD3475 Approved
0.7015 Intermediate Similarity NPD6822 Approved
0.7015 Intermediate Similarity NPD1919 Approved
0.7015 Intermediate Similarity NPD1920 Approved
0.7015 Intermediate Similarity NPD3476 Approved
0.7009 Intermediate Similarity NPD1419 Approved
0.7009 Intermediate Similarity NPD1417 Approved
0.7008 Intermediate Similarity NPD3499 Approved
0.7008 Intermediate Similarity NPD3498 Approved
0.7007 Intermediate Similarity NPD4411 Phase 1
0.7007 Intermediate Similarity NPD4410 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD3864 Clinical (unspecified phase)
0.6978 Remote Similarity NPD1902 Approved
0.6978 Remote Similarity NPD1904 Approved
0.6972 Remote Similarity NPD5839 Clinical (unspecified phase)
0.6964 Remote Similarity NPD2998 Approved
0.6964 Remote Similarity NPD2997 Approved
0.6964 Remote Similarity NPD3000 Approved
0.695 Remote Similarity NPD2866 Approved
0.694 Remote Similarity NPD947 Approved
0.694 Remote Similarity NPD1001 Discontinued
0.6935 Remote Similarity NPD3149 Approved
0.6935 Remote Similarity NPD2659 Approved
0.6935 Remote Similarity NPD3150 Approved
0.6935 Remote Similarity NPD3148 Approved
0.6935 Remote Similarity NPD3147 Approved
0.6935 Remote Similarity NPD2658 Approved
0.6929 Remote Similarity NPD1903 Approved
0.6929 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7461 Approved
0.6923 Remote Similarity NPD478 Approved
0.6923 Remote Similarity NPD3622 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3623 Clinical (unspecified phase)
0.6912 Remote Similarity NPD7200 Approved
0.6901 Remote Similarity NPD4509 Discontinued
0.6901 Remote Similarity NPD5254 Discontinued
0.6901 Remote Similarity NPD3401 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6575 Clinical (unspecified phase)
0.6897 Remote Similarity NPD8355 Approved
0.6897 Remote Similarity NPD8353 Approved
0.6894 Remote Similarity NPD6900 Discontinued
0.6879 Remote Similarity NPD5526 Phase 2
0.6879 Remote Similarity NPD5527 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1306 Clinical (unspecified phase)
0.687 Remote Similarity NPD2938 Approved
0.687 Remote Similarity NPD2940 Approved
0.6866 Remote Similarity NPD3424 Clinical (unspecified phase)
0.6861 Remote Similarity NPD3944 Approved
0.6861 Remote Similarity NPD3942 Approved
0.6861 Remote Similarity NPD6821 Approved
0.6861 Remote Similarity NPD4028 Approved
0.6861 Remote Similarity NPD4030 Approved
0.6861 Remote Similarity NPD4029 Approved
0.686 Remote Similarity NPD2243 Clinical (unspecified phase)
0.6855 Remote Similarity NPD1762 Approved
0.6855 Remote Similarity NPD1764 Approved
0.6849 Remote Similarity NPD2882 Phase 1
0.6838 Remote Similarity NPD1251 Discontinued
0.6828 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6828 Remote Similarity NPD5538 Clinical (unspecified phase)
0.6828 Remote Similarity NPD3100 Discontinued
0.6825 Remote Similarity NPD1720 Phase 2
0.6825 Remote Similarity NPD1723 Phase 2
0.6825 Remote Similarity NPD2622 Approved
0.6812 Remote Similarity NPD2867 Approved
0.6806 Remote Similarity NPD1886 Approved
0.6803 Remote Similarity NPD8354 Approved
0.6794 Remote Similarity NPD5787 Discontinued
0.6791 Remote Similarity NPD995 Clinical (unspecified phase)
0.6789 Remote Similarity NPD2539 Approved
0.6789 Remote Similarity NPD2538 Approved
0.6786 Remote Similarity NPD6606 Clinical (unspecified phase)
0.6783 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6772 Remote Similarity NPD6660 Discontinued
0.6769 Remote Similarity NPD4811 Discontinued
0.6765 Remote Similarity NPD715 Phase 3
0.6759 Remote Similarity NPD4547 Phase 3
0.6739 Remote Similarity NPD6318 Clinical (unspecified phase)
0.6738 Remote Similarity NPD1953 Discontinued
0.6736 Remote Similarity NPD3630 Approved
0.6736 Remote Similarity NPD3629 Approved
0.6735 Remote Similarity NPD6707 Clinical (unspecified phase)
0.6723 Remote Similarity NPD708 Approved
0.6721 Remote Similarity NPD458 Approved
0.6719 Remote Similarity NPD153 Clinical (unspecified phase)
0.6718 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6718 Remote Similarity NPD270 Clinical (unspecified phase)
0.6718 Remote Similarity NPD271 Approved
0.6718 Remote Similarity NPD268 Approved
0.6716 Remote Similarity NPD6713 Approved
0.6716 Remote Similarity NPD6712 Approved
0.6715 Remote Similarity NPD3137 Clinical (unspecified phase)
0.6713 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6713 Remote Similarity NPD2006 Phase 2
0.6711 Remote Similarity NPD7091 Discontinued
0.6696 Remote Similarity NPD6549 Approved
0.6696 Remote Similarity NPD6548 Approved
0.6694 Remote Similarity NPD156 Phase 3
0.6692 Remote Similarity NPD1525 Approved
0.6691 Remote Similarity NPD5782 Phase 3
0.6691 Remote Similarity NPD2399 Clinical (unspecified phase)
0.669 Remote Similarity NPD4402 Clinical (unspecified phase)
0.669 Remote Similarity NPD7469 Discontinued
0.6667 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3011 Approved
0.6667 Remote Similarity NPD1396 Approved
0.6667 Remote Similarity NPD991 Phase 2
0.6667 Remote Similarity NPD1865 Approved
0.6667 Remote Similarity NPD6017 Discontinued
0.6667 Remote Similarity NPD3012 Approved
0.6667 Remote Similarity NPD2915 Discontinued

  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