Structure

Physi-Chem Properties

Molecular Weight:  259.08
Volume:  255.37
LogP:  2.957
LogD:  3.098
LogS:  -3.901
# Rotatable Bonds:  3
TPSA:  53.72
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.723
Synthetic Accessibility Score:  2.522
Fsp3:  0.214
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.782
MDCK Permeability:  3.257233038311824e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.136
Plasma Protein Binding (PPB):  84.5543441772461%
Volume Distribution (VD):  0.472
Pgp-substrate:  9.792699813842773%

ADMET: Metabolism

CYP1A2-inhibitor:  0.978
CYP1A2-substrate:  0.957
CYP2C19-inhibitor:  0.866
CYP2C19-substrate:  0.81
CYP2C9-inhibitor:  0.564
CYP2C9-substrate:  0.891
CYP2D6-inhibitor:  0.688
CYP2D6-substrate:  0.92
CYP3A4-inhibitor:  0.821
CYP3A4-substrate:  0.513

ADMET: Excretion

Clearance (CL):  10.182
Half-life (T1/2):  0.531

ADMET: Toxicity

hERG Blockers:  0.06
Human Hepatotoxicity (H-HT):  0.197
Drug-inuced Liver Injury (DILI):  0.942
AMES Toxicity:  0.656
Rat Oral Acute Toxicity:  0.511
Maximum Recommended Daily Dose:  0.16
Skin Sensitization:  0.466
Carcinogencity:  0.425
Eye Corrosion:  0.003
Eye Irritation:  0.101
Respiratory Toxicity:  0.883

Download Data

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

  Natural Product: NPC140296

Natural Product ID:  NPC140296
Common Name*:   4,6,8-Trimethoxyfuro[2,3-B]Quinoline
IUPAC Name:   4,6,8-trimethoxyfuro[2,3-b]quinoline
Synonyms:  
Standard InCHIKey:  SHAVHFJCSQWTFF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H13NO4/c1-16-8-6-10-12(11(7-8)17-2)15-14-9(4-5-19-14)13(10)18-3/h4-7H,1-3H3
SMILES:  COc1cc(OC)c2c(c1)c(OC)c1c(n2)occ1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1966898
PubChem CID:   68222
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
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16406 Leptospermum recurvum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16000 Cetorhinus maximus Species Alopiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13941 Aeollanthus buchnerianus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21284 Cynoglossum viridiflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20279 Parmelia damaziana Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15500 Aconitum volubile Species Ranunculaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 71121.35 nM PMID[458371]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 41686.94 nM PMID[458371]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 33728.73 nM PMID[458371]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 94841.85 nM PMID[458371]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 45708.82 nM PMID[458371]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 61944.11 nM PMID[458371]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 99540.54 nM PMID[458371]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 66374.31 nM PMID[458371]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 55718.57 nM PMID[458371]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 27733.2 nM PMID[458371]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 37068.07 nM PMID[458371]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 83176.38 nM PMID[458371]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 41591.06 nM PMID[458371]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 67764.15 nM PMID[458371]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 76032.63 nM PMID[458371]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 30408.85 nM PMID[458371]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 64714.26 nM PMID[458371]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 97498.96 nM PMID[458371]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 77983.01 nM PMID[458371]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 61235.04 nM PMID[458371]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 77446.18 nM PMID[458371]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 62805.84 nM PMID[458371]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 96382.9 nM PMID[458371]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 79983.43 nM PMID[458371]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[458371]

☑ 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 NPC140296 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
0.9602 High Similarity NPC131885
0.9275 High Similarity NPC205372
0.9245 High Similarity NPC34770
0.9167 High Similarity NPC16066
0.9132 High Similarity NPC173250
0.9091 High Similarity NPC203373
0.8991 High Similarity NPC166712
0.8971 High Similarity NPC269367
0.895 High Similarity NPC160100
0.895 High Similarity NPC208364
0.89 High Similarity NPC298436
0.8889 High Similarity NPC120513
0.8869 High Similarity NPC58209
0.8837 High Similarity NPC217176
0.8692 High Similarity NPC97746
0.8559 High Similarity NPC168922
0.8496 Intermediate Similarity NPC1608
0.8475 Intermediate Similarity NPC101312
0.8444 Intermediate Similarity NPC188400
0.8143 Intermediate Similarity NPC230683
0.8054 Intermediate Similarity NPC314633
0.7798 Intermediate Similarity NPC187501
0.7736 Intermediate Similarity NPC112937
0.7713 Intermediate Similarity NPC208084
0.7636 Intermediate Similarity NPC146418
0.7634 Intermediate Similarity NPC288987
0.7613 Intermediate Similarity NPC185197
0.7591 Intermediate Similarity NPC219664
0.7568 Intermediate Similarity NPC39500
0.7523 Intermediate Similarity NPC203168
0.7522 Intermediate Similarity NPC225279
0.7511 Intermediate Similarity NPC46561
0.7489 Intermediate Similarity NPC45190
0.748 Intermediate Similarity NPC209981
0.7467 Intermediate Similarity NPC179287
0.7454 Intermediate Similarity NPC280714
0.7434 Intermediate Similarity NPC184408
0.7417 Intermediate Similarity NPC161801
0.739 Intermediate Similarity NPC470042
0.7381 Intermediate Similarity NPC42591
0.7375 Intermediate Similarity NPC72715
0.7319 Intermediate Similarity NPC329631
0.7315 Intermediate Similarity NPC196449
0.7315 Intermediate Similarity NPC314222
0.7308 Intermediate Similarity NPC474688
0.7304 Intermediate Similarity NPC144452
0.7302 Intermediate Similarity NPC79293
0.7302 Intermediate Similarity NPC279401
0.7294 Intermediate Similarity NPC220408
0.7289 Intermediate Similarity NPC310211
0.7289 Intermediate Similarity NPC308137
0.7288 Intermediate Similarity NPC39370
0.728 Intermediate Similarity NPC148889
0.7277 Intermediate Similarity NPC473186
0.7273 Intermediate Similarity NPC66815
0.7261 Intermediate Similarity NPC198503
0.7252 Intermediate Similarity NPC300156
0.7244 Intermediate Similarity NPC294375
0.7243 Intermediate Similarity NPC45389
0.724 Intermediate Similarity NPC317572
0.723 Intermediate Similarity NPC66083
0.7229 Intermediate Similarity NPC282346
0.7227 Intermediate Similarity NPC477589
0.7227 Intermediate Similarity NPC6786
0.7227 Intermediate Similarity NPC477587
0.7222 Intermediate Similarity NPC230403
0.7222 Intermediate Similarity NPC274640
0.722 Intermediate Similarity NPC321428
0.722 Intermediate Similarity NPC249583
0.7184 Intermediate Similarity NPC67401
0.7167 Intermediate Similarity NPC477586
0.7167 Intermediate Similarity NPC477585
0.7167 Intermediate Similarity NPC477590
0.7167 Intermediate Similarity NPC477588
0.7162 Intermediate Similarity NPC169402
0.7157 Intermediate Similarity NPC118511
0.7149 Intermediate Similarity NPC116238
0.7149 Intermediate Similarity NPC118228
0.7143 Intermediate Similarity NPC469439
0.7143 Intermediate Similarity NPC283117
0.7143 Intermediate Similarity NPC193238
0.7143 Intermediate Similarity NPC475190
0.7137 Intermediate Similarity NPC475844
0.7137 Intermediate Similarity NPC119134
0.713 Intermediate Similarity NPC174576
0.713 Intermediate Similarity NPC247803
0.7114 Intermediate Similarity NPC473188
0.7107 Intermediate Similarity NPC124300
0.7103 Intermediate Similarity NPC194040
0.71 Intermediate Similarity NPC148409
0.7085 Intermediate Similarity NPC41216
0.7083 Intermediate Similarity NPC144381
0.708 Intermediate Similarity NPC185782
0.7078 Intermediate Similarity NPC291609
0.7075 Intermediate Similarity NPC474798
0.7073 Intermediate Similarity NPC165964
0.7069 Intermediate Similarity NPC150239
0.7069 Intermediate Similarity NPC174760
0.7061 Intermediate Similarity NPC26679
0.7061 Intermediate Similarity NPC472098
0.7059 Intermediate Similarity NPC196718
0.7059 Intermediate Similarity NPC102593
0.7047 Intermediate Similarity NPC227824
0.7039 Intermediate Similarity NPC280799
0.702 Intermediate Similarity NPC310618
0.7008 Intermediate Similarity NPC100734
0.7008 Intermediate Similarity NPC88923
0.7008 Intermediate Similarity NPC315634
0.7 Intermediate Similarity NPC53534
0.6992 Remote Similarity NPC470018
0.6991 Remote Similarity NPC4687
0.6987 Remote Similarity NPC38237
0.6987 Remote Similarity NPC474428
0.6984 Remote Similarity NPC191489
0.6979 Remote Similarity NPC94842
0.6976 Remote Similarity NPC137353
0.6962 Remote Similarity NPC257851
0.696 Remote Similarity NPC287208
0.6949 Remote Similarity NPC473449
0.6946 Remote Similarity NPC474701
0.6944 Remote Similarity NPC284685
0.694 Remote Similarity NPC293151
0.6936 Remote Similarity NPC251071
0.6935 Remote Similarity NPC134637
0.6934 Remote Similarity NPC283152
0.6932 Remote Similarity NPC318068
0.693 Remote Similarity NPC62069
0.6923 Remote Similarity NPC472099
0.6917 Remote Similarity NPC89549
0.6913 Remote Similarity NPC264176
0.691 Remote Similarity NPC195120
0.6907 Remote Similarity NPC51388
0.6903 Remote Similarity NPC470930
0.6902 Remote Similarity NPC152620
0.6897 Remote Similarity NPC8022
0.6897 Remote Similarity NPC470799
0.6892 Remote Similarity NPC472435
0.6891 Remote Similarity NPC157931
0.6886 Remote Similarity NPC82548
0.6883 Remote Similarity NPC30749
0.6883 Remote Similarity NPC268223
0.6881 Remote Similarity NPC242928
0.6877 Remote Similarity NPC129897
0.6872 Remote Similarity NPC304183
0.687 Remote Similarity NPC87413
0.6865 Remote Similarity NPC472589
0.6851 Remote Similarity NPC157983
0.6851 Remote Similarity NPC118154
0.684 Remote Similarity NPC473800
0.6838 Remote Similarity NPC87560
0.6838 Remote Similarity NPC258048
0.6831 Remote Similarity NPC470017
0.683 Remote Similarity NPC128823
0.6829 Remote Similarity NPC72905
0.6826 Remote Similarity NPC470020
0.6824 Remote Similarity NPC3207
0.682 Remote Similarity NPC74575
0.6818 Remote Similarity NPC469390
0.6813 Remote Similarity NPC207620
0.6811 Remote Similarity NPC472436
0.681 Remote Similarity NPC476287
0.681 Remote Similarity NPC232225
0.6808 Remote Similarity NPC288943
0.6805 Remote Similarity NPC476999
0.6802 Remote Similarity NPC142385
0.6797 Remote Similarity NPC220337
0.6797 Remote Similarity NPC218303
0.6797 Remote Similarity NPC471978
0.6789 Remote Similarity NPC49672
0.6788 Remote Similarity NPC169716
0.6786 Remote Similarity NPC472588
0.6783 Remote Similarity NPC471979
0.6777 Remote Similarity NPC49547
0.6774 Remote Similarity NPC320394
0.6769 Remote Similarity NPC212123
0.6769 Remote Similarity NPC53344
0.6767 Remote Similarity NPC305542
0.6762 Remote Similarity NPC473187
0.6751 Remote Similarity NPC76478
0.675 Remote Similarity NPC478078
0.6748 Remote Similarity NPC475816
0.6747 Remote Similarity NPC107123
0.6739 Remote Similarity NPC86834
0.6739 Remote Similarity NPC210828
0.6738 Remote Similarity NPC324361
0.6734 Remote Similarity NPC75179
0.6733 Remote Similarity NPC26543
0.6732 Remote Similarity NPC26872
0.6729 Remote Similarity NPC84347
0.6725 Remote Similarity NPC472286
0.6725 Remote Similarity NPC472287
0.6724 Remote Similarity NPC23294
0.6724 Remote Similarity NPC9894
0.6723 Remote Similarity NPC216612
0.6722 Remote Similarity NPC311906
0.6722 Remote Similarity NPC476997
0.6722 Remote Similarity NPC194740
0.6721 Remote Similarity NPC253675
0.6715 Remote Similarity NPC26850
0.6712 Remote Similarity NPC61350

  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 NPC140296 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
0.7818 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD2778 Approved
0.7634 Intermediate Similarity NPD6974 Phase 3
0.7593 Intermediate Similarity NPD2779 Approved
0.7573 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD1505 Phase 2
0.7511 Intermediate Similarity NPD1166 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD3257 Approved
0.7333 Intermediate Similarity NPD3945 Discontinued
0.7319 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD4898 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD3006 Discontinued
0.7249 Intermediate Similarity NPD3258 Approved
0.7244 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD1867 Approved
0.7234 Intermediate Similarity NPD1466 Phase 3
0.7234 Intermediate Similarity NPD1467 Approved
0.7225 Intermediate Similarity NPD4667 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD7180 Phase 3
0.7215 Intermediate Similarity NPD2951 Discontinued
0.7208 Intermediate Similarity NPD7417 Discontinued
0.7205 Intermediate Similarity NPD4429 Discontinued
0.7191 Intermediate Similarity NPD5924 Discontinued
0.7191 Intermediate Similarity NPD5022 Discontinued
0.7179 Intermediate Similarity NPD4328 Approved
0.7178 Intermediate Similarity NPD6716 Phase 1
0.7175 Intermediate Similarity NPD3507 Phase 2
0.7168 Intermediate Similarity NPD5416 Discontinued
0.7167 Intermediate Similarity NPD3925 Approved
0.7167 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5482 Discontinued
0.7137 Intermediate Similarity NPD3263 Phase 3
0.7124 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD7853 Phase 2
0.7078 Intermediate Similarity NPD5512 Phase 3
0.7074 Intermediate Similarity NPD5293 Phase 2
0.7074 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7046 Intermediate Similarity NPD5479 Discontinued
0.7033 Intermediate Similarity NPD8102 Discontinued
0.7009 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD2285 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD7803 Approved
0.7 Intermediate Similarity NPD6550 Discontinued
0.7 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.6988 Remote Similarity NPD8463 Approved
0.6987 Remote Similarity NPD7031 Phase 1
0.6984 Remote Similarity NPD7708 Approved
0.6983 Remote Similarity NPD7395 Discontinued
0.6983 Remote Similarity NPD5632 Approved
0.6975 Remote Similarity NPD4952 Phase 3
0.6955 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6947 Remote Similarity NPD3842 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7955 Approved
0.6944 Remote Similarity NPD5256 Discontinued
0.6944 Remote Similarity NPD7956 Approved
0.694 Remote Similarity NPD5443 Clinical (unspecified phase)
0.6936 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6916 Remote Similarity NPD5429 Discontinued
0.69 Remote Similarity NPD3392 Approved
0.6888 Remote Similarity NPD4373 Phase 2
0.6883 Remote Similarity NPD5488 Discontinued
0.688 Remote Similarity NPD3875 Discontinued
0.6875 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4958 Clinical (unspecified phase)
0.687 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6790 Phase 1
0.6853 Remote Similarity NPD1638 Discovery
0.6849 Remote Similarity NPD5640 Discontinued
0.6831 Remote Similarity NPD3250 Phase 1
0.6826 Remote Similarity NPD648 Clinical (unspecified phase)
0.6826 Remote Similarity NPD2081 Clinical (unspecified phase)
0.682 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6812 Remote Similarity NPD7467 Discontinued
0.6809 Remote Similarity NPD5450 Discontinued
0.6808 Remote Similarity NPD5922 Phase 3
0.6803 Remote Similarity NPD4368 Phase 2
0.6802 Remote Similarity NPD4418 Discontinued
0.6769 Remote Similarity NPD7222 Phase 2
0.6763 Remote Similarity NPD1659 Phase 1
0.6763 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6761 Remote Similarity NPD1483 Discontinued
0.6761 Remote Similarity NPD7022 Phase 2
0.6754 Remote Similarity NPD1955 Discontinued
0.6754 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7885 Phase 2
0.6748 Remote Similarity NPD7886 Phase 2
0.6747 Remote Similarity NPD5817 Discontinued
0.6737 Remote Similarity NPD2884 Phase 1
0.6737 Remote Similarity NPD2899 Discontinued
0.6736 Remote Similarity NPD7284 Clinical (unspecified phase)
0.6734 Remote Similarity NPD6495 Clinical (unspecified phase)
0.6719 Remote Similarity NPD5532 Phase 2
0.6709 Remote Similarity NPD6242 Discontinued
0.6697 Remote Similarity NPD2564 Approved
0.6697 Remote Similarity NPD2565 Phase 2
0.6696 Remote Similarity NPD6321 Discontinued
0.6693 Remote Similarity NPD4369 Phase 2
0.668 Remote Similarity NPD8100 Phase 3
0.668 Remote Similarity NPD5857 Phase 3
0.6667 Remote Similarity NPD6962 Phase 2
0.6654 Remote Similarity NPD6252 Clinical (unspecified phase)
0.6641 Remote Similarity NPD6456 Discontinued
0.6639 Remote Similarity NPD5850 Phase 3
0.6624 Remote Similarity NPD5866 Approved
0.6623 Remote Similarity NPD7452 Approved
0.6623 Remote Similarity NPD7453 Approved
0.662 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6614 Remote Similarity NPD7859 Phase 2
0.6612 Remote Similarity NPD3259 Approved
0.6606 Remote Similarity NPD4203 Approved
0.6606 Remote Similarity NPD4204 Approved
0.6606 Remote Similarity NPD6104 Discontinued
0.6602 Remote Similarity NPD6961 Discontinued
0.6601 Remote Similarity NPD8101 Phase 3
0.6599 Remote Similarity NPD946 Discontinued
0.6599 Remote Similarity NPD4846 Phase 2
0.6593 Remote Similarity NPD5003 Discontinued
0.6588 Remote Similarity NPD2311 Clinical (unspecified phase)
0.6588 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6585 Remote Similarity NPD6963 Approved
0.6585 Remote Similarity NPD6964 Approved
0.6582 Remote Similarity NPD5164 Discontinued
0.6581 Remote Similarity NPD4502 Phase 2
0.658 Remote Similarity NPD4305 Clinical (unspecified phase)
0.6578 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6578 Remote Similarity NPD6590 Discontinued
0.6573 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7797 Approved
0.6571 Remote Similarity NPD7796 Approved
0.6571 Remote Similarity NPD3746 Discontinued
0.6568 Remote Similarity NPD4897 Phase 2
0.6565 Remote Similarity NPD5513 Phase 2
0.6561 Remote Similarity NPD4558 Phase 2
0.656 Remote Similarity NPD4322 Discontinued
0.6553 Remote Similarity NPD7069 Discontinued
0.6548 Remote Similarity NPD8359 Phase 2
0.6546 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6542 Remote Similarity NPD4923 Phase 1
0.6535 Remote Similarity NPD6874 Approved
0.6527 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6228 Discontinued
0.6522 Remote Similarity NPD7868 Clinical (unspecified phase)
0.652 Remote Similarity NPD6988 Phase 1
0.6516 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6504 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6502 Remote Similarity NPD7426 Phase 1
0.6491 Remote Similarity NPD772 Phase 3
0.6486 Remote Similarity NPD3801 Clinical (unspecified phase)
0.6485 Remote Similarity NPD6198 Phase 1
0.6478 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6475 Remote Similarity NPD7994 Phase 2
0.6475 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6475 Remote Similarity NPD3899 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3986 Discontinued
0.6471 Remote Similarity NPD6475 Phase 2
0.6466 Remote Similarity NPD5805 Approved
0.6459 Remote Similarity NPD4353 Phase 2
0.6457 Remote Similarity NPD3328 Phase 2
0.6457 Remote Similarity NPD6393 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5559 Phase 2
0.6447 Remote Similarity NPD6769 Clinical (unspecified phase)
0.6437 Remote Similarity NPD4885 Approved
0.6434 Remote Similarity NPD7603 Discontinued
0.6432 Remote Similarity NPD8479 Phase 2
0.6431 Remote Similarity NPD7872 Phase 2
0.6429 Remote Similarity NPD1898 Discontinued
0.6422 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6417 Remote Similarity NPD1926 Approved
0.6417 Remote Similarity NPD3354 Phase 2
0.6417 Remote Similarity NPD6568 Discontinued
0.6416 Remote Similarity NPD6745 Discontinued
0.6411 Remote Similarity NPD6625 Approved
0.6411 Remote Similarity NPD6494 Phase 2
0.6406 Remote Similarity NPD3809 Discontinued
0.6405 Remote Similarity NPD5507 Approved
0.6405 Remote Similarity NPD5506 Approved
0.6404 Remote Similarity NPD3478 Clinical (unspecified phase)
0.6404 Remote Similarity NPD3477 Phase 2
0.6398 Remote Similarity NPD6530 Approved
0.6398 Remote Similarity NPD6531 Approved
0.6398 Remote Similarity NPD5726 Clinical (unspecified phase)
0.6398 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6395 Remote Similarity NPD4039 Approved
0.6395 Remote Similarity NPD4034 Approved
0.6395 Remote Similarity NPD4038 Approved
0.6395 Remote Similarity NPD4033 Approved
0.6395 Remote Similarity NPD6138 Clinical (unspecified phase)
0.6395 Remote Similarity NPD4037 Approved
0.6395 Remote Similarity NPD4036 Approved
0.6395 Remote Similarity NPD4122 Approved
0.6395 Remote Similarity NPD4035 Approved
0.6395 Remote Similarity NPD31 Approved
0.6395 Remote Similarity NPD32 Approved
0.6391 Remote Similarity NPD1880 Phase 3
0.639 Remote Similarity NPD2785 Clinical (unspecified phase)
0.6387 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6385 Remote Similarity NPD8091 Phase 3
0.6383 Remote Similarity NPD5658 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