Structure

Physi-Chem Properties

Molecular Weight:  326.08
Volume:  317.308
LogP:  3.498
LogD:  3.043
LogS:  -5.669
# Rotatable Bonds:  3
TPSA:  67.13
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.736
Synthetic Accessibility Score:  2.29
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.851
MDCK Permeability:  6.584104266948998e-05
Pgp-inhibitor:  0.426
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.102
Plasma Protein Binding (PPB):  91.22077941894531%
Volume Distribution (VD):  0.515
Pgp-substrate:  6.454687595367432%

ADMET: Metabolism

CYP1A2-inhibitor:  0.967
CYP1A2-substrate:  0.79
CYP2C19-inhibitor:  0.971
CYP2C19-substrate:  0.146
CYP2C9-inhibitor:  0.811
CYP2C9-substrate:  0.935
CYP2D6-inhibitor:  0.942
CYP2D6-substrate:  0.939
CYP3A4-inhibitor:  0.959
CYP3A4-substrate:  0.232

ADMET: Excretion

Clearance (CL):  9.972
Half-life (T1/2):  0.227

ADMET: Toxicity

hERG Blockers:  0.102
Human Hepatotoxicity (H-HT):  0.214
Drug-inuced Liver Injury (DILI):  0.892
AMES Toxicity:  0.178
Rat Oral Acute Toxicity:  0.097
Maximum Recommended Daily Dose:  0.34
Skin Sensitization:  0.383
Carcinogencity:  0.876
Eye Corrosion:  0.004
Eye Irritation:  0.343
Respiratory Toxicity:  0.56

Download Data

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

  Natural Product: NPC153008

Natural Product ID:  NPC153008
Common Name*:   7-Methoxy-3-(6-Methoxy-1,3-Benzodioxol-5-Yl)Chromen-4-One
IUPAC Name:   7-methoxy-3-(6-methoxy-1,3-benzodioxol-5-yl)chromen-4-one
Synonyms:  
Standard InCHIKey:  MSPWKPQQHHCXLR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H14O6/c1-20-10-3-4-11-15(5-10)22-8-13(18(11)19)12-6-16-17(24-9-23-16)7-14(12)21-2/h3-8H,9H2,1-2H3
SMILES:  COc1ccc2c(c1)occ(c1cc3c(cc1OC)OCO3)c2=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1976532
PubChem CID:   343083
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002586] O-methylated isoflavonoids
          • [CHEMONTID:0002602] 7-O-methylated isoflavonoids
            • [CHEMONTID:0002689] 7-O-methylisoflavones

*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
NPO27819 0nomuraea turkmeniaca Species Streptosporangiaceae Bacteria n.a. n.a. n.a. PMID[17636954]
NPO26132 Buxus natalensis Species Buxaceae Eukaryota n.a. uMhalanga Rocks nature reserve, Durban, South Africa 2007-FEB PMID[20954721]
NPO26132 Buxus natalensis Species Buxaceae Eukaryota n.a. bark n.a. PMID[20954721]
NPO27442 Hippeastrum morelianum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[21105684]
NPO20249 Antheroporum pierrei Species Fabaceae Eukaryota n.a. twig n.a. PMID[21452840]
NPO20249 Antheroporum pierrei Species Fabaceae Eukaryota n.a. leaf n.a. PMID[21452840]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[21510636]
NPO27370 Hapsidospora irregularis Species n.a. Eukaryota n.a. n.a. n.a. PMID[28106998]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28172 Rheum palaestinum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27426 Cassytha melantha Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28172 Rheum palaestinum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27426 Cassytha melantha Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27442 Hippeastrum morelianum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27365 Polybia occidentalis Species Vespidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28225 Citrus bigaradia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27268 Cryptocarya densiflora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27370 Hapsidospora irregularis Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27503 Scombresox saurus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20249 Antheroporum pierrei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26132 Buxus natalensis Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27819 0nomuraea turkmeniaca Species Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28022 Baccharis genistifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27601 Perna canaliculus Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27720 Bagarius bagarius Species Sisoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28118 Halimeda monile Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28172 Rheum palaestinum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20929 Patellaria scruposa Species Patellariaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 43651.58 nM PMID[465673]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 32885.16 nM PMID[465673]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 41879.36 nM PMID[465673]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 59156.16 nM PMID[465673]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 55207.74 nM PMID[465673]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 51999.6 nM PMID[465673]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 61517.69 nM PMID[465673]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 56104.8 nM PMID[465673]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 93325.43 nM PMID[465673]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 72777.98 nM PMID[465673]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 97274.72 nM PMID[465673]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 51760.68 nM PMID[465673]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 58884.37 nM PMID[465673]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 37670.38 nM PMID[465673]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 60117.37 nM PMID[465673]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[465673]

☑ 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 NPC153008 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
1.0 High Similarity NPC148497
0.9932 High Similarity NPC478213
0.9796 High Similarity NPC57211
0.9795 High Similarity NPC279061
0.973 High Similarity NPC478238
0.9728 High Similarity NPC52623
0.9667 High Similarity NPC62518
0.9667 High Similarity NPC215375
0.96 High Similarity NPC167595
0.9595 High Similarity NPC292460
0.9539 High Similarity NPC260640
0.9539 High Similarity NPC295009
0.953 High Similarity NPC244371
0.9517 High Similarity NPC224687
0.9474 High Similarity NPC225624
0.9474 High Similarity NPC285973
0.947 High Similarity NPC258644
0.9463 High Similarity NPC68882
0.9452 High Similarity NPC120924
0.9452 High Similarity NPC216314
0.9452 High Similarity NPC195919
0.9384 High Similarity NPC296575
0.9351 High Similarity NPC18284
0.9351 High Similarity NPC273021
0.9351 High Similarity NPC478199
0.9333 High Similarity NPC104728
0.9333 High Similarity NPC35544
0.9315 High Similarity NPC182842
0.9281 High Similarity NPC257914
0.9281 High Similarity NPC104459
0.9281 High Similarity NPC238405
0.9272 High Similarity NPC279930
0.9221 High Similarity NPC131557
0.9216 High Similarity NPC310206
0.9211 High Similarity NPC284353
0.92 High Similarity NPC156953
0.9178 High Similarity NPC185607
0.9161 High Similarity NPC34376
0.9156 High Similarity NPC113055
0.915 High Similarity NPC155063
0.915 High Similarity NPC301897
0.9145 High Similarity NPC186507
0.9139 High Similarity NPC262623
0.9128 High Similarity NPC205522
0.911 High Similarity NPC58229
0.9103 High Similarity NPC469575
0.9091 High Similarity NPC19097
0.9079 High Similarity NPC100263
0.9079 High Similarity NPC291802
0.9079 High Similarity NPC216769
0.9079 High Similarity NPC245382
0.9079 High Similarity NPC131266
0.9079 High Similarity NPC209487
0.9079 High Similarity NPC35763
0.9079 High Similarity NPC121522
0.9079 High Similarity NPC181209
0.9079 High Similarity NPC100971
0.9079 High Similarity NPC269451
0.9073 High Similarity NPC234152
0.9073 High Similarity NPC239363
0.9067 High Similarity NPC63256
0.9067 High Similarity NPC10304
0.906 High Similarity NPC215932
0.906 High Similarity NPC40818
0.906 High Similarity NPC110639
0.906 High Similarity NPC106461
0.906 High Similarity NPC14958
0.906 High Similarity NPC231013
0.9051 High Similarity NPC113093
0.9045 High Similarity NPC470178
0.9038 High Similarity NPC162668
0.902 High Similarity NPC124714
0.9013 High Similarity NPC45291
0.9013 High Similarity NPC19980
0.9013 High Similarity NPC288316
0.9007 High Similarity NPC238366
0.9006 High Similarity NPC72455
0.9 High Similarity NPC85233
0.8994 High Similarity NPC135345
0.8993 High Similarity NPC136278
0.8993 High Similarity NPC471590
0.8987 High Similarity NPC187923
0.8986 High Similarity NPC476054
0.8981 High Similarity NPC302741
0.8974 High Similarity NPC269906
0.8968 High Similarity NPC474990
0.8961 High Similarity NPC39184
0.8947 High Similarity NPC10467
0.8944 High Similarity NPC223375
0.8944 High Similarity NPC475825
0.8938 High Similarity NPC41853
0.8933 High Similarity NPC283002
0.8933 High Similarity NPC12377
0.8933 High Similarity NPC302408
0.8926 High Similarity NPC113089
0.8926 High Similarity NPC23955
0.8917 High Similarity NPC94155
0.8904 High Similarity NPC44573
0.8896 High Similarity NPC280937
0.8896 High Similarity NPC472408
0.8896 High Similarity NPC250557
0.8896 High Similarity NPC128961
0.8889 High Similarity NPC220577
0.8882 High Similarity NPC200060
0.8882 High Similarity NPC40290
0.8882 High Similarity NPC264289
0.8882 High Similarity NPC69752
0.8882 High Similarity NPC105511
0.8882 High Similarity NPC69430
0.8882 High Similarity NPC195763
0.8882 High Similarity NPC142876
0.8882 High Similarity NPC139293
0.8882 High Similarity NPC264550
0.8882 High Similarity NPC333691
0.8875 High Similarity NPC167479
0.8875 High Similarity NPC42892
0.8875 High Similarity NPC76482
0.8874 High Similarity NPC474999
0.8874 High Similarity NPC93034
0.8874 High Similarity NPC119660
0.8867 High Similarity NPC165512
0.8861 High Similarity NPC125991
0.8859 High Similarity NPC9966
0.8859 High Similarity NPC70853
0.8854 High Similarity NPC298093
0.8839 High Similarity NPC134287
0.8839 High Similarity NPC18954
0.8839 High Similarity NPC130589
0.8834 High Similarity NPC66804
0.8831 High Similarity NPC166201
0.8828 High Similarity NPC143649
0.8827 High Similarity NPC475155
0.8827 High Similarity NPC475964
0.8827 High Similarity NPC205076
0.8827 High Similarity NPC48773
0.8827 High Similarity NPC307518
0.8824 High Similarity NPC259058
0.8824 High Similarity NPC201547
0.8824 High Similarity NPC306821
0.882 High Similarity NPC471287
0.8816 High Similarity NPC194653
0.8816 High Similarity NPC254702
0.8816 High Similarity NPC139364
0.8816 High Similarity NPC218490
0.8816 High Similarity NPC287395
0.8816 High Similarity NPC80710
0.8816 High Similarity NPC183655
0.8816 High Similarity NPC476058
0.8816 High Similarity NPC203747
0.8808 High Similarity NPC88345
0.8808 High Similarity NPC153620
0.8808 High Similarity NPC24257
0.8805 High Similarity NPC110257
0.8805 High Similarity NPC65846
0.88 High Similarity NPC293201
0.8797 High Similarity NPC470756
0.8792 High Similarity NPC124467
0.8792 High Similarity NPC29536
0.8792 High Similarity NPC214919
0.8782 High Similarity NPC180340
0.878 High Similarity NPC156635
0.8774 High Similarity NPC472915
0.8774 High Similarity NPC471981
0.8773 High Similarity NPC62640
0.8766 High Similarity NPC308451
0.8766 High Similarity NPC474663
0.8766 High Similarity NPC198615
0.8766 High Similarity NPC117579
0.8766 High Similarity NPC149614
0.8766 High Similarity NPC226973
0.8766 High Similarity NPC208043
0.8765 High Similarity NPC224462
0.8765 High Similarity NPC44558
0.8765 High Similarity NPC212748
0.8758 High Similarity NPC181250
0.8758 High Similarity NPC102003
0.8758 High Similarity NPC92722
0.8758 High Similarity NPC471288
0.875 High Similarity NPC470511
0.875 High Similarity NPC117463
0.875 High Similarity NPC125449
0.875 High Similarity NPC299923
0.875 High Similarity NPC188074
0.8742 High Similarity NPC81679
0.8727 High Similarity NPC67302
0.8726 High Similarity NPC476981
0.8726 High Similarity NPC210084
0.8726 High Similarity NPC181960
0.8726 High Similarity NPC99597
0.8726 High Similarity NPC78103
0.872 High Similarity NPC290304
0.872 High Similarity NPC236327
0.872 High Similarity NPC472607
0.8718 High Similarity NPC213622
0.8718 High Similarity NPC2928
0.8718 High Similarity NPC241774
0.8718 High Similarity NPC122623
0.8718 High Similarity NPC34725
0.8718 High Similarity NPC20830
0.8718 High Similarity NPC276059

  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 NPC153008 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
0.8875 High Similarity NPD3818 Discontinued
0.8874 High Similarity NPD6980 Clinical (unspecified phase)
0.8854 High Similarity NPD5494 Approved
0.8654 High Similarity NPD2801 Approved
0.8562 High Similarity NPD1247 Approved
0.8481 Intermediate Similarity NPD3817 Phase 2
0.8471 Intermediate Similarity NPD1934 Approved
0.8428 Intermediate Similarity NPD3882 Suspended
0.8383 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD7054 Approved
0.8333 Intermediate Similarity NPD2796 Approved
0.8323 Intermediate Similarity NPD919 Approved
0.8313 Intermediate Similarity NPD7074 Phase 3
0.8313 Intermediate Similarity NPD7472 Approved
0.8267 Intermediate Similarity NPD1510 Phase 2
0.8261 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD1511 Approved
0.8187 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8166 Intermediate Similarity NPD7808 Phase 3
0.8155 Intermediate Similarity NPD6797 Phase 2
0.8121 Intermediate Similarity NPD3926 Phase 2
0.8107 Intermediate Similarity NPD7251 Discontinued
0.8089 Intermediate Similarity NPD1512 Approved
0.8061 Intermediate Similarity NPD6232 Discontinued
0.8038 Intermediate Similarity NPD920 Approved
0.8024 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD4380 Phase 2
0.8 Intermediate Similarity NPD1240 Approved
0.7964 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD6166 Phase 2
0.7964 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6799 Approved
0.7947 Intermediate Similarity NPD1933 Approved
0.7914 Intermediate Similarity NPD5402 Approved
0.7911 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD37 Approved
0.7895 Intermediate Similarity NPD6559 Discontinued
0.7895 Intermediate Similarity NPD1607 Approved
0.7885 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD1549 Phase 2
0.7866 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD7819 Suspended
0.7824 Intermediate Similarity NPD5844 Phase 1
0.7824 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD1243 Approved
0.7806 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6801 Discontinued
0.7785 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7199 Phase 2
0.7778 Intermediate Similarity NPD6599 Discontinued
0.7763 Intermediate Similarity NPD943 Approved
0.7758 Intermediate Similarity NPD4967 Phase 2
0.7758 Intermediate Similarity NPD4966 Approved
0.7758 Intermediate Similarity NPD4965 Approved
0.7742 Intermediate Similarity NPD2935 Discontinued
0.7711 Intermediate Similarity NPD7075 Discontinued
0.7692 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD3748 Approved
0.7665 Intermediate Similarity NPD6234 Discontinued
0.7643 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD7411 Suspended
0.76 Intermediate Similarity NPD2798 Approved
0.7588 Intermediate Similarity NPD5242 Approved
0.7584 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2533 Approved
0.7578 Intermediate Similarity NPD2532 Approved
0.7578 Intermediate Similarity NPD2534 Approved
0.7578 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD5401 Approved
0.753 Intermediate Similarity NPD1465 Phase 2
0.7514 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3749 Approved
0.7485 Intermediate Similarity NPD5403 Approved
0.7484 Intermediate Similarity NPD447 Suspended
0.7484 Intermediate Similarity NPD230 Phase 1
0.7457 Intermediate Similarity NPD3751 Discontinued
0.7439 Intermediate Similarity NPD1653 Approved
0.7438 Intermediate Similarity NPD3750 Approved
0.7429 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD5005 Approved
0.7419 Intermediate Similarity NPD5006 Approved
0.741 Intermediate Similarity NPD6386 Approved
0.741 Intermediate Similarity NPD6385 Approved
0.7386 Intermediate Similarity NPD7685 Pre-registration
0.7381 Intermediate Similarity NPD5353 Approved
0.7381 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD2654 Approved
0.7375 Intermediate Similarity NPD2800 Approved
0.7372 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD7228 Approved
0.7326 Intermediate Similarity NPD3787 Discontinued
0.7297 Intermediate Similarity NPD4420 Approved
0.7296 Intermediate Similarity NPD1551 Phase 2
0.729 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD2313 Discontinued
0.7289 Intermediate Similarity NPD7458 Discontinued
0.7279 Intermediate Similarity NPD5536 Phase 2
0.7273 Intermediate Similarity NPD6832 Phase 2
0.7267 Intermediate Similarity NPD6959 Discontinued
0.7267 Intermediate Similarity NPD3705 Approved
0.7267 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2344 Approved
0.7241 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7768 Phase 2
0.7233 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3027 Phase 3
0.7219 Intermediate Similarity NPD6777 Approved
0.7219 Intermediate Similarity NPD6780 Approved
0.7219 Intermediate Similarity NPD6776 Approved
0.7219 Intermediate Similarity NPD6778 Approved
0.7219 Intermediate Similarity NPD6779 Approved
0.7219 Intermediate Similarity NPD6782 Approved
0.7219 Intermediate Similarity NPD6781 Approved
0.7208 Intermediate Similarity NPD9494 Approved
0.7191 Intermediate Similarity NPD7240 Approved
0.7186 Intermediate Similarity NPD3226 Approved
0.7143 Intermediate Similarity NPD2403 Approved
0.7143 Intermediate Similarity NPD2346 Discontinued
0.7125 Intermediate Similarity NPD2799 Discontinued
0.7117 Intermediate Similarity NPD4628 Phase 3
0.7105 Intermediate Similarity NPD7696 Phase 3
0.7105 Intermediate Similarity NPD7697 Approved
0.7105 Intermediate Similarity NPD3972 Approved
0.7105 Intermediate Similarity NPD7698 Approved
0.7105 Intermediate Similarity NPD7435 Discontinued
0.7097 Intermediate Similarity NPD3018 Phase 2
0.7089 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1613 Approved
0.7073 Intermediate Similarity NPD2309 Approved
0.7073 Intermediate Similarity NPD6190 Approved
0.7068 Intermediate Similarity NPD7870 Phase 2
0.7068 Intermediate Similarity NPD7871 Phase 2
0.7056 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7028 Phase 2
0.7039 Intermediate Similarity NPD5953 Discontinued
0.7037 Intermediate Similarity NPD1471 Phase 3
0.7037 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD5710 Approved
0.7029 Intermediate Similarity NPD5711 Approved
0.7022 Intermediate Similarity NPD7286 Phase 2
0.7017 Intermediate Similarity NPD8313 Approved
0.7017 Intermediate Similarity NPD8312 Approved
0.7013 Intermediate Similarity NPD1876 Approved
0.701 Intermediate Similarity NPD8151 Discontinued
0.7 Intermediate Similarity NPD6651 Approved
0.6995 Remote Similarity NPD8434 Phase 2
0.6993 Remote Similarity NPD2981 Phase 2
0.6988 Remote Similarity NPD4357 Discontinued
0.6987 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6981 Remote Similarity NPD4307 Phase 2
0.6977 Remote Similarity NPD5978 Approved
0.6977 Remote Similarity NPD5977 Approved
0.6968 Remote Similarity NPD3266 Approved
0.6968 Remote Similarity NPD3267 Approved
0.6963 Remote Similarity NPD6823 Phase 2
0.6959 Remote Similarity NPD7701 Phase 2
0.6959 Remote Similarity NPD6844 Discontinued
0.6954 Remote Similarity NPD9268 Approved
0.6952 Remote Similarity NPD6534 Approved
0.6952 Remote Similarity NPD6535 Approved
0.6949 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2982 Phase 2
0.6948 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2983 Phase 2
0.6932 Remote Similarity NPD7229 Phase 3
0.6923 Remote Similarity NPD1019 Discontinued
0.6914 Remote Similarity NPD7033 Discontinued
0.6908 Remote Similarity NPD17 Approved
0.6907 Remote Similarity NPD7584 Approved
0.6905 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6892 Remote Similarity NPD5283 Phase 1
0.6888 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6888 Remote Similarity NPD7874 Approved
0.6886 Remote Similarity NPD7390 Discontinued
0.6885 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6883 Remote Similarity NPD9269 Phase 2
0.6872 Remote Similarity NPD7893 Clinical (unspecified phase)
0.686 Remote Similarity NPD6280 Approved
0.686 Remote Similarity NPD6279 Approved
0.6859 Remote Similarity NPD1203 Approved
0.6855 Remote Similarity NPD1296 Phase 2
0.6855 Remote Similarity NPD3764 Approved
0.6853 Remote Similarity NPD7801 Approved
0.6842 Remote Similarity NPD7699 Phase 2
0.6842 Remote Similarity NPD7700 Phase 2
0.6836 Remote Similarity NPD6808 Phase 2
0.6829 Remote Similarity NPD7266 Discontinued
0.6829 Remote Similarity NPD2343 Clinical (unspecified phase)
0.681 Remote Similarity NPD4308 Phase 3
0.6782 Remote Similarity NPD4288 Approved
0.6779 Remote Similarity NPD1241 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