Structure

Physi-Chem Properties

Molecular Weight:  764.43
Volume:  764.16
LogP:  4.186
LogD:  2.783
LogS:  -3.628
# Rotatable Bonds:  6
TPSA:  212.67
# H-Bond Aceptor:  13
# H-Bond Donor:  7
# Rings:  7
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.152
Synthetic Accessibility Score:  5.736
Fsp3:  0.902
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.002
MDCK Permeability:  9.484564543527085e-06
Pgp-inhibitor:  0.202
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.74
20% Bioavailability (F20%):  0.126
30% Bioavailability (F30%):  0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.068
Plasma Protein Binding (PPB):  87.6445541381836%
Volume Distribution (VD):  0.428
Pgp-substrate:  11.06110954284668%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.424
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.178
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.027
CYP2D6-substrate:  0.093
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.012

ADMET: Excretion

Clearance (CL):  0.778
Half-life (T1/2):  0.507

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.192
Drug-inuced Liver Injury (DILI):  0.019
AMES Toxicity:  0.068
Rat Oral Acute Toxicity:  0.097
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.035
Carcinogencity:  0.056
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.964

Download Data

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

  Natural Product: NPC208364

Natural Product ID:  NPC208364
Common Name*:   Kokusagine
IUPAC Name:   n.a.
Synonyms:   Kokusagine
Standard InCHIKey:  SDPOFOYJCOPMMV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H9NO4/c1-15-11-7-2-3-9-12(18-6-17-9)10(7)14-13-8(11)4-5-16-13/h2-5H,6H2,1H3
SMILES:  COc1c2ccc3c(c2nc2c1cco2)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL491782
PubChem CID:   5318829
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0002374] Furanoquinolines

*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
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. Wrocław, Poland 2004–2005 DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635 Glycine max Species Fabaceae 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]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/jf950732o]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10775096]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[15568765]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. root n.a. PMID[1622242]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16659156]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16668466]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[20963508]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO7635 Glycine max Species Fabaceae Eukaryota Seeds Tekirdag, Turkey PMID[24499198]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25053043]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25070365]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25369450]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. seed n.a. PMID[25369450]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Hypocotyl n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota Testa n.a. n.a. Database[FooDB]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. seed n.a. Database[MetaboLights]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO7635 Glycine max Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7635 Glycine max Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO340 Orixa japonica Species Rutaceae 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
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 16.0 ug.mL-1 PMID[488254]

☑ 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 NPC208364 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
0.9817 High Similarity NPC173250
0.9673 High Similarity NPC34770
0.9554 High Similarity NPC120513
0.9409 High Similarity NPC166712
0.9406 High Similarity NPC168922
0.9367 High Similarity NPC160100
0.9283 High Similarity NPC58209
0.9159 High Similarity NPC203373
0.9156 High Similarity NPC1608
0.9087 High Similarity NPC217176
0.9025 High Similarity NPC101312
0.895 High Similarity NPC140296
0.893 High Similarity NPC131885
0.8716 High Similarity NPC298436
0.869 High Similarity NPC188400
0.8643 High Similarity NPC205372
0.852 High Similarity NPC97746
0.8364 Intermediate Similarity NPC16066
0.8349 Intermediate Similarity NPC269367
0.8018 Intermediate Similarity NPC219664
0.7946 Intermediate Similarity NPC203168
0.772 Intermediate Similarity NPC230683
0.7623 Intermediate Similarity NPC66815
0.7607 Intermediate Similarity NPC314633
0.7586 Intermediate Similarity NPC208084
0.7571 Intermediate Similarity NPC473188
0.7511 Intermediate Similarity NPC148409
0.7511 Intermediate Similarity NPC146418
0.75 Intermediate Similarity NPC185197
0.7397 Intermediate Similarity NPC253675
0.7373 Intermediate Similarity NPC209981
0.7358 Intermediate Similarity NPC124300
0.7354 Intermediate Similarity NPC470042
0.7353 Intermediate Similarity NPC179287
0.7328 Intermediate Similarity NPC291609
0.7319 Intermediate Similarity NPC87560
0.7319 Intermediate Similarity NPC195120
0.7289 Intermediate Similarity NPC112937
0.7284 Intermediate Similarity NPC187501
0.7269 Intermediate Similarity NPC310618
0.7257 Intermediate Similarity NPC118154
0.7257 Intermediate Similarity NPC157983
0.7248 Intermediate Similarity NPC88923
0.7248 Intermediate Similarity NPC315634
0.7248 Intermediate Similarity NPC100734
0.7246 Intermediate Similarity NPC46561
0.7227 Intermediate Similarity NPC89549
0.7222 Intermediate Similarity NPC39500
0.7188 Intermediate Similarity NPC284685
0.7186 Intermediate Similarity NPC474595
0.7185 Intermediate Similarity NPC225279
0.7179 Intermediate Similarity NPC310211
0.7179 Intermediate Similarity NPC308137
0.7177 Intermediate Similarity NPC119134
0.7155 Intermediate Similarity NPC198503
0.7154 Intermediate Similarity NPC314222
0.7154 Intermediate Similarity NPC196449
0.7149 Intermediate Similarity NPC474594
0.7143 Intermediate Similarity NPC288987
0.7137 Intermediate Similarity NPC303374
0.7131 Intermediate Similarity NPC169402
0.7131 Intermediate Similarity NPC474688
0.7125 Intermediate Similarity NPC144452
0.7119 Intermediate Similarity NPC116238
0.7112 Intermediate Similarity NPC249583
0.7108 Intermediate Similarity NPC475844
0.7101 Intermediate Similarity NPC184408
0.7093 Intermediate Similarity NPC191489
0.7092 Intermediate Similarity NPC124313
0.708 Intermediate Similarity NPC84164
0.708 Intermediate Similarity NPC207283
0.7072 Intermediate Similarity NPC204385
0.7049 Intermediate Similarity NPC274640
0.7047 Intermediate Similarity NPC165964
0.7045 Intermediate Similarity NPC39370
0.7043 Intermediate Similarity NPC318068
0.7042 Intermediate Similarity NPC174760
0.704 Intermediate Similarity NPC207620
0.7037 Intermediate Similarity NPC200888
0.7036 Intermediate Similarity NPC161801
0.7035 Intermediate Similarity NPC79293
0.7035 Intermediate Similarity NPC279401
0.7029 Intermediate Similarity NPC247803
0.7028 Intermediate Similarity NPC166722
0.7014 Intermediate Similarity NPC169716
0.7 Intermediate Similarity NPC282346
0.6988 Remote Similarity NPC182907
0.6988 Remote Similarity NPC129897
0.6988 Remote Similarity NPC189903
0.6988 Remote Similarity NPC6786
0.6988 Remote Similarity NPC472436
0.6983 Remote Similarity NPC41216
0.698 Remote Similarity NPC134637
0.6971 Remote Similarity NPC150239
0.6968 Remote Similarity NPC206201
0.6966 Remote Similarity NPC4687
0.6964 Remote Similarity NPC473186
0.6958 Remote Similarity NPC227824
0.6955 Remote Similarity NPC287152
0.6953 Remote Similarity NPC183537
0.6948 Remote Similarity NPC108342
0.6941 Remote Similarity NPC270515
0.6938 Remote Similarity NPC472435
0.6935 Remote Similarity NPC329631
0.6933 Remote Similarity NPC268223
0.6923 Remote Similarity NPC476999
0.6923 Remote Similarity NPC45190
0.691 Remote Similarity NPC207971
0.691 Remote Similarity NPC317572
0.6905 Remote Similarity NPC148889
0.6905 Remote Similarity NPC99891
0.6904 Remote Similarity NPC148391
0.689 Remote Similarity NPC472434
0.6887 Remote Similarity NPC77878
0.6887 Remote Similarity NPC67401
0.6886 Remote Similarity NPC254957
0.6885 Remote Similarity NPC94842
0.6883 Remote Similarity NPC280714
0.688 Remote Similarity NPC268077
0.6875 Remote Similarity NPC42591
0.6867 Remote Similarity NPC22481
0.6863 Remote Similarity NPC107123
0.6862 Remote Similarity NPC114468
0.6853 Remote Similarity NPC477587
0.6853 Remote Similarity NPC184680
0.6853 Remote Similarity NPC477589
0.6849 Remote Similarity NPC87413
0.6844 Remote Similarity NPC471978
0.6838 Remote Similarity NPC49672
0.6833 Remote Similarity NPC2905
0.6833 Remote Similarity NPC118228
0.683 Remote Similarity NPC471979
0.683 Remote Similarity NPC62069
0.6828 Remote Similarity NPC45389
0.6825 Remote Similarity NPC470785
0.6822 Remote Similarity NPC473800
0.682 Remote Similarity NPC264176
0.6818 Remote Similarity NPC134702
0.6813 Remote Similarity NPC473187
0.6812 Remote Similarity NPC230403
0.6809 Remote Similarity NPC470930
0.6805 Remote Similarity NPC3207
0.6803 Remote Similarity NPC76478
0.6802 Remote Similarity NPC13249
0.68 Remote Similarity NPC172222
0.6798 Remote Similarity NPC477586
0.6798 Remote Similarity NPC477588
0.6798 Remote Similarity NPC477590
0.6798 Remote Similarity NPC41501
0.6798 Remote Similarity NPC477585
0.6797 Remote Similarity NPC72715
0.6795 Remote Similarity NPC119818
0.6795 Remote Similarity NPC2173
0.6795 Remote Similarity NPC328700
0.6795 Remote Similarity NPC202771
0.6787 Remote Similarity NPC474701
0.6781 Remote Similarity NPC234197
0.678 Remote Similarity NPC300156
0.6776 Remote Similarity NPC148124
0.6774 Remote Similarity NPC476997
0.6774 Remote Similarity NPC194740
0.6773 Remote Similarity NPC90875
0.6772 Remote Similarity NPC210296
0.6767 Remote Similarity NPC14622
0.6767 Remote Similarity NPC71124
0.6767 Remote Similarity NPC215098
0.6767 Remote Similarity NPC73020
0.6767 Remote Similarity NPC124302
0.6767 Remote Similarity NPC46744
0.6767 Remote Similarity NPC70290
0.6763 Remote Similarity NPC146976
0.6762 Remote Similarity NPC469439
0.6762 Remote Similarity NPC54066
0.6761 Remote Similarity NPC470018
0.676 Remote Similarity NPC196718
0.676 Remote Similarity NPC102593
0.6758 Remote Similarity NPC78609
0.6757 Remote Similarity NPC133609
0.6756 Remote Similarity NPC258048
0.6751 Remote Similarity NPC321428
0.675 Remote Similarity NPC472098
0.6749 Remote Similarity NPC182853
0.6749 Remote Similarity NPC174576
0.6748 Remote Similarity NPC51388
0.6747 Remote Similarity NPC476996
0.6747 Remote Similarity NPC278525
0.6747 Remote Similarity NPC476998
0.6739 Remote Similarity NPC475190
0.6738 Remote Similarity NPC5374
0.6738 Remote Similarity NPC220408
0.6735 Remote Similarity NPC99724
0.6735 Remote Similarity NPC118189
0.6722 Remote Similarity NPC236668
0.6721 Remote Similarity NPC46451
0.6719 Remote Similarity NPC476995
0.6718 Remote Similarity NPC53534
0.6709 Remote Similarity NPC314100
0.6709 Remote Similarity NPC304183
0.6709 Remote Similarity NPC120671
0.6709 Remote Similarity NPC72788

  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 NPC208364 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
0.7417 Intermediate Similarity NPD1505 Phase 2
0.7382 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD6974 Phase 3
0.732 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD2778 Approved
0.7248 Intermediate Similarity NPD7803 Approved
0.7191 Intermediate Similarity NPD4667 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7955 Approved
0.7188 Intermediate Similarity NPD7956 Approved
0.7165 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD2779 Approved
0.716 Intermediate Similarity NPD4898 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD6716 Phase 1
0.7126 Intermediate Similarity NPD4846 Phase 2
0.7102 Intermediate Similarity NPD4885 Approved
0.7101 Intermediate Similarity NPD7690 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7708 Approved
0.709 Intermediate Similarity NPD5924 Discontinued
0.7061 Intermediate Similarity NPD1867 Approved
0.7054 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7180 Phase 3
0.7021 Intermediate Similarity NPD1166 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD3006 Discontinued
0.7004 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.698 Remote Similarity NPD5482 Discontinued
0.6965 Remote Similarity NPD5532 Phase 2
0.6958 Remote Similarity NPD5632 Approved
0.6951 Remote Similarity NPD4952 Phase 3
0.6935 Remote Similarity NPD6625 Approved
0.6935 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6926 Remote Similarity NPD3925 Approved
0.6926 Remote Similarity NPD6247 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1467 Approved
0.6923 Remote Similarity NPD3507 Phase 2
0.6923 Remote Similarity NPD1466 Phase 3
0.692 Remote Similarity NPD5805 Approved
0.6905 Remote Similarity NPD7417 Discontinued
0.6904 Remote Similarity NPD3257 Approved
0.6904 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6898 Remote Similarity NPD3263 Phase 3
0.6885 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6883 Remote Similarity NPD5022 Discontinued
0.688 Remote Similarity NPD7853 Phase 2
0.687 Remote Similarity NPD4328 Approved
0.6867 Remote Similarity NPD4373 Phase 2
0.6865 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6865 Remote Similarity NPD7885 Phase 2
0.6865 Remote Similarity NPD7886 Phase 2
0.6862 Remote Similarity NPD3945 Discontinued
0.686 Remote Similarity NPD2899 Discontinued
0.6826 Remote Similarity NPD5512 Phase 3
0.6824 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6816 Remote Similarity NPD5459 Phase 2
0.6815 Remote Similarity NPD5479 Discontinued
0.6806 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6798 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6795 Remote Similarity NPD5006 Approved
0.6795 Remote Similarity NPD7859 Phase 2
0.6795 Remote Similarity NPD5005 Approved
0.6791 Remote Similarity NPD5922 Phase 3
0.679 Remote Similarity NPD3258 Approved
0.6787 Remote Similarity NPD6962 Phase 2
0.6786 Remote Similarity NPD4368 Phase 2
0.6784 Remote Similarity NPD6495 Clinical (unspecified phase)
0.6778 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6776 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6773 Remote Similarity NPD6964 Approved
0.6773 Remote Similarity NPD6963 Approved
0.6773 Remote Similarity NPD2951 Discontinued
0.6772 Remote Similarity NPD6790 Phase 1
0.6768 Remote Similarity NPD6228 Discontinued
0.6767 Remote Similarity NPD4420 Approved
0.6753 Remote Similarity NPD6550 Discontinued
0.6749 Remote Similarity NPD7395 Discontinued
0.6749 Remote Similarity NPD4429 Discontinued
0.6745 Remote Similarity NPD1483 Discontinued
0.6745 Remote Similarity NPD6517 Phase 3
0.6731 Remote Similarity NPD5857 Phase 3
0.6721 Remote Similarity NPD3763 Approved
0.6705 Remote Similarity NPD3328 Phase 2
0.6694 Remote Similarity NPD5640 Discontinued
0.6681 Remote Similarity NPD5429 Discontinued
0.668 Remote Similarity NPD5866 Approved
0.6667 Remote Similarity NPD5450 Discontinued
0.6641 Remote Similarity NPD6252 Clinical (unspecified phase)
0.664 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6639 Remote Similarity NPD683 Approved
0.6639 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6639 Remote Similarity NPD5416 Discontinued
0.6627 Remote Similarity NPD7031 Phase 1
0.6626 Remote Similarity NPD5293 Phase 2
0.6626 Remote Similarity NPD1638 Discovery
0.6615 Remote Similarity NPD8102 Discontinued
0.6612 Remote Similarity NPD3816 Phase 1
0.6612 Remote Similarity NPD3815 Phase 1
0.6602 Remote Similarity NPD5488 Discontinued
0.6602 Remote Similarity NPD5817 Discontinued
0.6601 Remote Similarity NPD6494 Phase 2
0.66 Remote Similarity NPD3259 Approved
0.6597 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6587 Remote Similarity NPD7284 Clinical (unspecified phase)
0.6585 Remote Similarity NPD6745 Discontinued
0.6583 Remote Similarity NPD5658 Approved
0.6578 Remote Similarity NPD3920 Phase 2
0.6578 Remote Similarity NPD8463 Approved
0.6571 Remote Similarity NPD5443 Clinical (unspecified phase)
0.6567 Remote Similarity NPD6456 Discontinued
0.6566 Remote Similarity NPD8091 Phase 3
0.655 Remote Similarity NPD7022 Phase 2
0.655 Remote Similarity NPD5256 Discontinued
0.6535 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6534 Remote Similarity NPD8459 Approved
0.6534 Remote Similarity NPD8460 Approved
0.6529 Remote Similarity NPD648 Clinical (unspecified phase)
0.6528 Remote Similarity NPD8255 Phase 2
0.6523 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6518 Remote Similarity NPD3875 Discontinued
0.6513 Remote Similarity NPD956 Clinical (unspecified phase)
0.6498 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6496 Remote Similarity NPD4418 Discontinued
0.6496 Remote Similarity NPD6861 Clinical (unspecified phase)
0.649 Remote Similarity NPD7538 Clinical (unspecified phase)
0.649 Remote Similarity NPD5903 Approved
0.649 Remote Similarity NPD5902 Approved
0.6475 Remote Similarity NPD8359 Phase 2
0.6468 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6461 Remote Similarity NPD3392 Approved
0.6452 Remote Similarity NPD5519 Discontinued
0.6449 Remote Similarity NPD8465 Approved
0.6449 Remote Similarity NPD8466 Approved
0.6449 Remote Similarity NPD8467 Approved
0.6429 Remote Similarity NPD7426 Phase 1
0.6429 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6426 Remote Similarity NPD5850 Phase 3
0.6426 Remote Similarity NPD5930 Phase 3
0.642 Remote Similarity NPD3250 Phase 1
0.6417 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6417 Remote Similarity NPD1659 Phase 1
0.6405 Remote Similarity NPD7222 Phase 2
0.6403 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6402 Remote Similarity NPD6243 Phase 3
0.6402 Remote Similarity NPD6244 Phase 3
0.6395 Remote Similarity NPD2564 Approved
0.6395 Remote Similarity NPD2565 Phase 2
0.6393 Remote Similarity NPD2081 Clinical (unspecified phase)
0.6393 Remote Similarity NPD5914 Approved
0.6392 Remote Similarity NPD3441 Approved
0.6392 Remote Similarity NPD3442 Approved
0.639 Remote Similarity NPD3217 Phase 2
0.6386 Remote Similarity NPD2785 Clinical (unspecified phase)
0.6383 Remote Similarity NPD1955 Discontinued
0.6381 Remote Similarity NPD8461 Discontinued
0.6379 Remote Similarity NPD7467 Discontinued
0.6377 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6367 Remote Similarity NPD3746 Discontinued
0.6364 Remote Similarity NPD3842 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4369 Phase 2
0.636 Remote Similarity NPD8479 Phase 2
0.6357 Remote Similarity NPD8425 Approved
0.6357 Remote Similarity NPD8426 Approved
0.635 Remote Similarity NPD8364 Approved
0.635 Remote Similarity NPD8363 Approved
0.6341 Remote Similarity NPD7069 Discontinued
0.634 Remote Similarity NPD3924 Approved
0.634 Remote Similarity NPD3986 Discontinued
0.634 Remote Similarity NPD3923 Approved
0.634 Remote Similarity NPD3921 Approved
0.634 Remote Similarity NPD3922 Approved
0.6333 Remote Similarity NPD6321 Discontinued
0.6331 Remote Similarity NPD8428 Approved
0.6331 Remote Similarity NPD8427 Approved
0.6331 Remote Similarity NPD8429 Approved
0.632 Remote Similarity NPD2884 Phase 1
0.6314 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6311 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6304 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6303 Remote Similarity NPD5003 Discontinued
0.6303 Remote Similarity NPD6988 Phase 1
0.6302 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6302 Remote Similarity NPD7013 Phase 3
0.6302 Remote Similarity NPD7012 Phase 3
0.6301 Remote Similarity NPD4502 Phase 2
0.6299 Remote Similarity NPD7223 Discontinued
0.6299 Remote Similarity NPD7224 Discontinued
0.6296 Remote Similarity NPD3003 Approved
0.629 Remote Similarity NPD7559 Phase 2
0.6288 Remote Similarity NPD8100 Phase 3
0.6287 Remote Similarity NPD6590 Discontinued
0.6283 Remote Similarity NPD6961 Discontinued
0.628 Remote Similarity NPD1926 Approved
0.6279 Remote Similarity NPD7558 Phase 2
0.6276 Remote Similarity NPD772 Phase 3
0.6275 Remote Similarity NPD7994 Phase 2
0.6275 Remote Similarity NPD3899 Clinical (unspecified phase)
0.627 Remote Similarity NPD7452 Approved
0.627 Remote Similarity NPD7453 Approved
0.6269 Remote Similarity NPD2311 Clinical (unspecified phase)
0.6269 Remote Similarity NPD946 Discontinued
0.6265 Remote Similarity NPD8067 Phase 3
0.626 Remote Similarity NPD4900 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data