Structure

Physi-Chem Properties

Molecular Weight:  240.08
Volume:  250.242
LogP:  4.185
LogD:  3.085
LogS:  -4.153
# Rotatable Bonds:  1
TPSA:  53.6
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.631
Synthetic Accessibility Score:  2.74
Fsp3:  0.067
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:  -4.957
MDCK Permeability:  1.4654734513896983e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.38
30% Bioavailability (F30%):  0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  96.26482391357422%
Volume Distribution (VD):  0.611
Pgp-substrate:  8.41658878326416%

ADMET: Metabolism

CYP1A2-inhibitor:  0.983
CYP1A2-substrate:  0.289
CYP2C19-inhibitor:  0.468
CYP2C19-substrate:  0.116
CYP2C9-inhibitor:  0.635
CYP2C9-substrate:  0.56
CYP2D6-inhibitor:  0.593
CYP2D6-substrate:  0.473
CYP3A4-inhibitor:  0.21
CYP3A4-substrate:  0.12

ADMET: Excretion

Clearance (CL):  8.874
Half-life (T1/2):  0.538

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.176
Drug-inuced Liver Injury (DILI):  0.968
AMES Toxicity:  0.438
Rat Oral Acute Toxicity:  0.699
Maximum Recommended Daily Dose:  0.855
Skin Sensitization:  0.927
Carcinogencity:  0.762
Eye Corrosion:  0.003
Eye Irritation:  0.842
Respiratory Toxicity:  0.813

Download Data

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

  Natural Product: NPC470764

Natural Product ID:  NPC470764
Common Name*:   Dehydroiso-Alpha-Lapachone
IUPAC Name:   2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
Synonyms:   Dehydroiso-Alpha-Lapachone
Standard InCHIKey:  ZDMOREUAQLXRCQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O3/c1-8(2)12-7-11-13(16)9-5-3-4-6-10(9)14(17)15(11)18-12/h3-6,12H,1,7H2,2H3
SMILES:  CC(=C)C1CC2=C(O1)C(=O)c1c(C2=O)cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL221630
PubChem CID:   364109
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO20768 Ekmanianthe longiflora Species Bignoniaceae Eukaryota roots n.a. n.a. PMID[10785421]
NPO8246 Lantana involucrata Species Verbenaceae Eukaryota n.a. n.a. n.a. PMID[15217280]
NPO8246 Lantana involucrata Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20768 Ekmanianthe longiflora Species Bignoniaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 1460.0 nM PMID[470810]
NPT1851 Cell Line Col2 Homo sapiens ED50 = 0.2 ug ml-1 PMID[470811]
NPT91 Cell Line KB Homo sapiens ED50 = 0.2 ug ml-1 PMID[470811]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 0.2 ug ml-1 PMID[470811]
NPT2345 Cell Line SW626 Homo sapiens ED50 = 0.3 ug ml-1 PMID[470811]
NPT136 Cell Line SK-N-SH Homo sapiens ED50 = 0.2 ug ml-1 PMID[470811]
NPT726 Cell Line M109 Mus musculus ED50 = 0.4 ug ml-1 PMID[470811]
NPT91 Cell Line KB Homo sapiens IC50 = 4100.0 nM PMID[470812]
NPT91 Cell Line KB Homo sapiens IC50 = 3500.0 nM PMID[470812]
NPT91 Cell Line KB Homo sapiens IC50 = 3200.0 nM PMID[470812]
NPT81 Cell Line A549 Homo sapiens IC50 = 6400.0 nM PMID[470812]
NPT309 Cell Line 1A9 Homo sapiens IC50 = 2600.0 nM PMID[470812]
NPT309 Cell Line 1A9 Homo sapiens IC50 = 2800.0 nM PMID[470812]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 1200.0 nM PMID[470812]
NPT307 Cell Line HOS Homo sapiens IC50 = 4000.0 nM PMID[470812]
NPT308 Cell Line CAKI-1 Homo sapiens IC50 > 10000.0 nM PMID[470812]
NPT308 Cell Line CAKI-1 Homo sapiens Inhibition = 26.0 % PMID[470812]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 11.67 nM PMID[470813]
NPT90 Cell Line DU-145 Homo sapiens Inhibition = 100.0 % PMID[470813]
NPT941 Cell Line HaCaT Homo sapiens IC50 = 4300.0 nM PMID[470814]
NPT179 Cell Line A2780 Homo sapiens GI50 = 2600.0 nM PMID[470815]
NPT1723 Cell Line HBL-100 Homo sapiens GI50 = 2300.0 nM PMID[470815]
NPT165 Cell Line HeLa Homo sapiens GI50 = 2100.0 nM PMID[470815]
NPT1577 Cell Line SW1573 Homo sapiens GI50 = 1900.0 nM PMID[470815]
NPT396 Cell Line T47D Homo sapiens GI50 = 21000.0 nM PMID[470815]
NPT1183 Cell Line WiDr Homo sapiens GI50 = 2700.0 nM PMID[470815]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 19098.53 nM PMID[470816]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 18879.91 nM PMID[470816]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 3380.65 nM PMID[470816]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 16330.52 nM PMID[470816]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 18535.32 nM PMID[470816]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 14028.14 nM PMID[470816]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 18578.04 nM PMID[470816]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 10568.18 nM PMID[470816]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 18923.44 nM PMID[470816]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 19633.6 nM PMID[470816]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 17338.04 nM PMID[470816]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 16481.62 nM PMID[470816]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 17418.07 nM PMID[470816]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 29785.16 nM PMID[470816]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 22961.49 nM PMID[470816]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 4120.98 nM PMID[470816]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 23550.49 nM PMID[470816]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 20749.14 nM PMID[470816]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 18323.14 nM PMID[470816]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 18492.69 nM PMID[470816]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 17947.34 nM PMID[470816]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 20989.4 nM PMID[470816]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 15135.61 nM PMID[470816]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 11271.97 nM PMID[470816]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 9183.33 nM PMID[470816]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 19098.53 nM PMID[470816]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 20989.4 nM PMID[470816]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 17579.24 nM PMID[470816]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 17864.88 nM PMID[470816]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 25703.96 nM PMID[470816]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 17218.69 nM PMID[470816]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 16032.45 nM PMID[470816]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[470816]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 17660.38 nM PMID[470816]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 16069.41 nM PMID[470816]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 17579.24 nM PMID[470816]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 19998.62 nM PMID[470816]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 20276.83 nM PMID[470816]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 20276.83 nM PMID[470816]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 13273.94 nM PMID[470816]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 16255.49 nM PMID[470816]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 20796.97 nM PMID[470816]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 20892.96 nM PMID[470816]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 10000.0 nM PMID[470816]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 18967.06 nM PMID[470816]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 19319.68 nM PMID[470816]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 18879.91 nM PMID[470816]
NPT35 Others n.a. LogP = 3.4 n.a. PMID[470810]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 1.0 ug ml-1 PMID[470811]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.2 ug ml-1 PMID[470811]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.3 ug ml-1 PMID[470811]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.5 ug ml-1 PMID[470811]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5700.0 nM PMID[470812]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2600.0 nM PMID[470812]
NPT314 Organism Bacillus cereus Bacillus cereus MIC > 78.12 ug.mL-1 PMID[470817]
NPT19 Organism Escherichia coli Escherichia coli MIC > 78.12 ug.mL-1 PMID[470817]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 325500.0 nM PMID[470817]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MBC = 81.38 uM PMID[470817]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 40670.0 nM PMID[470817]

☑ 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 NPC470764 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
0.9537 High Similarity NPC241851
0.9159 High Similarity NPC470391
0.9009 High Similarity NPC477411
0.8983 High Similarity NPC236405
0.8957 High Similarity NPC105709
0.8909 High Similarity NPC291799
0.8909 High Similarity NPC137315
0.885 High Similarity NPC226093
0.8774 High Similarity NPC112552
0.8727 High Similarity NPC192577
0.8595 High Similarity NPC81135
0.8559 High Similarity NPC144547
0.8522 High Similarity NPC135730
0.8509 High Similarity NPC196075
0.8475 Intermediate Similarity NPC289432
0.8475 Intermediate Similarity NPC988
0.8468 Intermediate Similarity NPC203732
0.844 Intermediate Similarity NPC274443
0.8421 Intermediate Similarity NPC13784
0.8417 Intermediate Similarity NPC65627
0.839 Intermediate Similarity NPC204784
0.8362 Intermediate Similarity NPC62138
0.8349 Intermediate Similarity NPC244427
0.8349 Intermediate Similarity NPC222390
0.8348 Intermediate Similarity NPC326664
0.8333 Intermediate Similarity NPC212415
0.8319 Intermediate Similarity NPC238861
0.8319 Intermediate Similarity NPC77000
0.8288 Intermediate Similarity NPC172483
0.8276 Intermediate Similarity NPC228936
0.8217 Intermediate Similarity NPC232996
0.8197 Intermediate Similarity NPC51079
0.819 Intermediate Similarity NPC67377
0.812 Intermediate Similarity NPC474408
0.8087 Intermediate Similarity NPC210089
0.807 Intermediate Similarity NPC83628
0.807 Intermediate Similarity NPC265407
0.8065 Intermediate Similarity NPC476599
0.8019 Intermediate Similarity NPC476484
0.8017 Intermediate Similarity NPC292834
0.8017 Intermediate Similarity NPC232958
0.8 Intermediate Similarity NPC318173
0.7984 Intermediate Similarity NPC295664
0.7982 Intermediate Similarity NPC156021
0.7966 Intermediate Similarity NPC474095
0.7939 Intermediate Similarity NPC38158
0.7937 Intermediate Similarity NPC478162
0.7937 Intermediate Similarity NPC478165
0.7931 Intermediate Similarity NPC474157
0.7917 Intermediate Similarity NPC323440
0.7917 Intermediate Similarity NPC222968
0.7917 Intermediate Similarity NPC80605
0.7917 Intermediate Similarity NPC61651
0.7909 Intermediate Similarity NPC145052
0.7903 Intermediate Similarity NPC318067
0.7903 Intermediate Similarity NPC328107
0.7895 Intermediate Similarity NPC30594
0.7895 Intermediate Similarity NPC37622
0.7881 Intermediate Similarity NPC307651
0.7807 Intermediate Similarity NPC134120
0.7807 Intermediate Similarity NPC209632
0.7797 Intermediate Similarity NPC272524
0.7797 Intermediate Similarity NPC161611
0.7797 Intermediate Similarity NPC143768
0.7786 Intermediate Similarity NPC23894
0.7769 Intermediate Similarity NPC477407
0.775 Intermediate Similarity NPC149691
0.7739 Intermediate Similarity NPC119271
0.7736 Intermediate Similarity NPC157778
0.7731 Intermediate Similarity NPC308744
0.7727 Intermediate Similarity NPC12695
0.7724 Intermediate Similarity NPC473243
0.7719 Intermediate Similarity NPC114594
0.7692 Intermediate Similarity NPC477412
0.7674 Intermediate Similarity NPC471832
0.7672 Intermediate Similarity NPC56493
0.7667 Intermediate Similarity NPC474685
0.7661 Intermediate Similarity NPC50872
0.7652 Intermediate Similarity NPC474659
0.7647 Intermediate Similarity NPC128368
0.7642 Intermediate Similarity NPC43945
0.7638 Intermediate Similarity NPC328997
0.7638 Intermediate Similarity NPC294050
0.7634 Intermediate Similarity NPC477406
0.7632 Intermediate Similarity NPC89886
0.7632 Intermediate Similarity NPC60679
0.763 Intermediate Similarity NPC477408
0.7627 Intermediate Similarity NPC474057
0.7627 Intermediate Similarity NPC167504
0.7619 Intermediate Similarity NPC182646
0.7612 Intermediate Similarity NPC284184
0.7612 Intermediate Similarity NPC301341
0.7607 Intermediate Similarity NPC17417
0.7607 Intermediate Similarity NPC269023
0.7607 Intermediate Similarity NPC10251
0.7607 Intermediate Similarity NPC474364
0.7607 Intermediate Similarity NPC99846
0.7597 Intermediate Similarity NPC237225
0.7594 Intermediate Similarity NPC309056
0.7594 Intermediate Similarity NPC217914
0.7593 Intermediate Similarity NPC173413
0.7593 Intermediate Similarity NPC303967
0.7593 Intermediate Similarity NPC67585
0.7593 Intermediate Similarity NPC110420
0.7586 Intermediate Similarity NPC100767
0.7583 Intermediate Similarity NPC196673
0.7578 Intermediate Similarity NPC177925
0.7576 Intermediate Similarity NPC310662
0.7565 Intermediate Similarity NPC31786
0.7563 Intermediate Similarity NPC82899
0.7563 Intermediate Similarity NPC79496
0.7563 Intermediate Similarity NPC186128
0.7563 Intermediate Similarity NPC270699
0.7557 Intermediate Similarity NPC205360
0.7556 Intermediate Similarity NPC173980
0.7544 Intermediate Similarity NPC45613
0.7542 Intermediate Similarity NPC174099
0.7542 Intermediate Similarity NPC214067
0.7542 Intermediate Similarity NPC196246
0.7542 Intermediate Similarity NPC93084
0.7542 Intermediate Similarity NPC251854
0.7541 Intermediate Similarity NPC469843
0.7523 Intermediate Similarity NPC284475
0.7521 Intermediate Similarity NPC211439
0.7521 Intermediate Similarity NPC210092
0.7519 Intermediate Similarity NPC316553
0.7519 Intermediate Similarity NPC212207
0.75 Intermediate Similarity NPC469547
0.75 Intermediate Similarity NPC103048
0.7481 Intermediate Similarity NPC27659
0.7481 Intermediate Similarity NPC198305
0.7481 Intermediate Similarity NPC119542
0.748 Intermediate Similarity NPC152812
0.748 Intermediate Similarity NPC471553
0.748 Intermediate Similarity NPC325740
0.748 Intermediate Similarity NPC135062
0.7479 Intermediate Similarity NPC305912
0.7479 Intermediate Similarity NPC260818
0.7479 Intermediate Similarity NPC1082
0.7478 Intermediate Similarity NPC247976
0.7456 Intermediate Similarity NPC473325
0.7456 Intermediate Similarity NPC70624
0.7455 Intermediate Similarity NPC1682
0.7455 Intermediate Similarity NPC188844
0.7455 Intermediate Similarity NPC155232
0.7444 Intermediate Similarity NPC171968
0.7442 Intermediate Similarity NPC51037
0.7442 Intermediate Similarity NPC51292
0.744 Intermediate Similarity NPC476225
0.7436 Intermediate Similarity NPC83409
0.7436 Intermediate Similarity NPC185763
0.7426 Intermediate Similarity NPC265181
0.7424 Intermediate Similarity NPC279596
0.7422 Intermediate Similarity NPC472694
0.7422 Intermediate Similarity NPC246166
0.7422 Intermediate Similarity NPC472693
0.7417 Intermediate Similarity NPC321852
0.7414 Intermediate Similarity NPC329282
0.7414 Intermediate Similarity NPC249067
0.7405 Intermediate Similarity NPC49272
0.7402 Intermediate Similarity NPC223351
0.7402 Intermediate Similarity NPC164947
0.7398 Intermediate Similarity NPC190298
0.7391 Intermediate Similarity NPC320891
0.7387 Intermediate Similarity NPC238219
0.7385 Intermediate Similarity NPC45537
0.7381 Intermediate Similarity NPC472981
0.7377 Intermediate Similarity NPC306740
0.7377 Intermediate Similarity NPC217111
0.7373 Intermediate Similarity NPC470007
0.7373 Intermediate Similarity NPC112903
0.7368 Intermediate Similarity NPC476042
0.7368 Intermediate Similarity NPC309430
0.7364 Intermediate Similarity NPC133461
0.736 Intermediate Similarity NPC202015
0.736 Intermediate Similarity NPC476645
0.7355 Intermediate Similarity NPC474176
0.7355 Intermediate Similarity NPC470253
0.7345 Intermediate Similarity NPC276775
0.7345 Intermediate Similarity NPC270654
0.7345 Intermediate Similarity NPC249912
0.7345 Intermediate Similarity NPC92754
0.7344 Intermediate Similarity NPC228739
0.7344 Intermediate Similarity NPC141252
0.7344 Intermediate Similarity NPC11799
0.7333 Intermediate Similarity NPC265513
0.7328 Intermediate Similarity NPC301943
0.7328 Intermediate Similarity NPC165257
0.7328 Intermediate Similarity NPC474365
0.7317 Intermediate Similarity NPC100353
0.7317 Intermediate Similarity NPC260886
0.7313 Intermediate Similarity NPC254603
0.7311 Intermediate Similarity NPC475282
0.7311 Intermediate Similarity NPC469636
0.7311 Intermediate Similarity NPC85493
0.7308 Intermediate Similarity NPC146239
0.7308 Intermediate Similarity NPC231774
0.7305 Intermediate Similarity NPC474630
0.7304 Intermediate Similarity NPC42211
0.7297 Intermediate Similarity NPC153885

  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 NPC470764 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
0.8333 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.8319 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD2067 Discontinued
0.7642 Intermediate Similarity NPD650 Approved
0.7607 Intermediate Similarity NPD2182 Approved
0.7565 Intermediate Similarity NPD164 Approved
0.7523 Intermediate Similarity NPD7609 Phase 3
0.7521 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD7631 Approved
0.7426 Intermediate Similarity NPD1471 Phase 3
0.7414 Intermediate Similarity NPD1237 Approved
0.7287 Intermediate Similarity NPD1876 Approved
0.7217 Intermediate Similarity NPD1238 Approved
0.7179 Intermediate Similarity NPD1930 Approved
0.7179 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1929 Approved
0.7154 Intermediate Similarity NPD1241 Discontinued
0.7109 Intermediate Similarity NPD4879 Approved
0.7094 Intermediate Similarity NPD1932 Approved
0.7073 Intermediate Similarity NPD7094 Approved
0.7073 Intermediate Similarity NPD6858 Approved
0.7043 Intermediate Similarity NPD3495 Discontinued
0.7042 Intermediate Similarity NPD7236 Approved
0.7015 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3972 Approved
0.6991 Remote Similarity NPD1508 Approved
0.6957 Remote Similarity NPD1989 Approved
0.6923 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2066 Phase 3
0.6912 Remote Similarity NPD7961 Discontinued
0.6889 Remote Similarity NPD7008 Discontinued
0.6885 Remote Similarity NPD2329 Discontinued
0.685 Remote Similarity NPD405 Clinical (unspecified phase)
0.6833 Remote Similarity NPD5909 Discontinued
0.6825 Remote Similarity NPD5951 Approved
0.6822 Remote Similarity NPD1651 Approved
0.681 Remote Similarity NPD1843 Approved
0.6809 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6803 Remote Similarity NPD7239 Suspended
0.6794 Remote Similarity NPD6287 Discontinued
0.6759 Remote Similarity NPD942 Approved
0.6759 Remote Similarity NPD3950 Discontinued
0.6748 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4878 Approved
0.6724 Remote Similarity NPD688 Clinical (unspecified phase)
0.6724 Remote Similarity NPD1693 Approved
0.6716 Remote Similarity NPD1470 Approved
0.6696 Remote Similarity NPD1282 Approved
0.6696 Remote Similarity NPD1087 Approved
0.6693 Remote Similarity NPD2629 Approved
0.669 Remote Similarity NPD2346 Discontinued
0.6667 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2788 Approved
0.6667 Remote Similarity NPD1281 Approved
0.6641 Remote Similarity NPD3317 Approved
0.6641 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6638 Remote Similarity NPD1202 Approved
0.6638 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6619 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6615 Remote Similarity NPD9545 Approved
0.6615 Remote Similarity NPD7009 Phase 2
0.6612 Remote Similarity NPD6647 Phase 2
0.6607 Remote Similarity NPD9257 Approved
0.6607 Remote Similarity NPD9259 Approved
0.6594 Remote Similarity NPD3764 Approved
0.6573 Remote Similarity NPD2344 Approved
0.6569 Remote Similarity NPD7055 Discontinued
0.656 Remote Similarity NPD1317 Discontinued
0.6555 Remote Similarity NPD9495 Approved
0.6554 Remote Similarity NPD6273 Approved
0.6547 Remote Similarity NPD7713 Phase 3
0.6544 Remote Similarity NPD2798 Approved
0.6541 Remote Similarity NPD518 Clinical (unspecified phase)
0.6541 Remote Similarity NPD1201 Approved
0.6538 Remote Similarity NPD7610 Discontinued
0.6522 Remote Similarity NPD3673 Approved
0.6522 Remote Similarity NPD1086 Approved
0.6522 Remote Similarity NPD1090 Approved
0.6522 Remote Similarity NPD3672 Approved
0.6522 Remote Similarity NPD1089 Approved
0.6519 Remote Similarity NPD1283 Approved
0.6507 Remote Similarity NPD3887 Approved
0.6503 Remote Similarity NPD2796 Approved
0.6496 Remote Similarity NPD1563 Approved
0.6494 Remote Similarity NPD7057 Phase 3
0.6494 Remote Similarity NPD7058 Phase 2
0.6493 Remote Similarity NPD6637 Approved
0.6484 Remote Similarity NPD6010 Discontinued
0.6475 Remote Similarity NPD2313 Discontinued
0.6466 Remote Similarity NPD1239 Approved
0.6439 Remote Similarity NPD5691 Approved
0.6438 Remote Similarity NPD4628 Phase 3
0.6435 Remote Similarity NPD800 Approved
0.6434 Remote Similarity NPD2799 Discontinued
0.6434 Remote Similarity NPD3748 Approved
0.6424 Remote Similarity NPD3226 Approved
0.6422 Remote Similarity NPD9490 Approved
0.6412 Remote Similarity NPD2347 Approved
0.6412 Remote Similarity NPD6065 Approved
0.641 Remote Similarity NPD1088 Approved
0.6403 Remote Similarity NPD6039 Approved
0.6397 Remote Similarity NPD5667 Approved
0.6395 Remote Similarity NPD2309 Approved
0.6391 Remote Similarity NPD17 Approved
0.6391 Remote Similarity NPD2932 Approved
0.6385 Remote Similarity NPD4198 Discontinued
0.6383 Remote Similarity NPD3140 Approved
0.6383 Remote Similarity NPD2979 Phase 3
0.6383 Remote Similarity NPD3142 Approved
0.6379 Remote Similarity NPD9258 Approved
0.6379 Remote Similarity NPD9256 Approved
0.6364 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6345 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6345 Remote Similarity NPD2353 Approved
0.6339 Remote Similarity NPD9491 Approved
0.6338 Remote Similarity NPD6355 Discontinued
0.6336 Remote Similarity NPD9493 Approved
0.6333 Remote Similarity NPD1565 Approved
0.6333 Remote Similarity NPD1564 Approved
0.6333 Remote Similarity NPD1566 Phase 3
0.6331 Remote Similarity NPD6832 Phase 2
0.633 Remote Similarity NPD225 Approved
0.633 Remote Similarity NPD227 Approved
0.6327 Remote Similarity NPD7003 Approved
0.6319 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6316 Remote Similarity NPD3024 Approved
0.6316 Remote Similarity NPD3025 Approved
0.6316 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6312 Remote Similarity NPD8032 Phase 2
0.6308 Remote Similarity NPD4766 Approved
0.6301 Remote Similarity NPD2897 Discontinued
0.6294 Remote Similarity NPD1607 Approved
0.6277 Remote Similarity NPD2198 Approved
0.6277 Remote Similarity NPD2199 Approved
0.6276 Remote Similarity NPD2438 Suspended
0.6275 Remote Similarity NPD6599 Discontinued
0.6269 Remote Similarity NPD3019 Approved
0.6269 Remote Similarity NPD2345 Approved
0.6268 Remote Similarity NPD4307 Phase 2
0.6268 Remote Similarity NPD1240 Approved
0.6261 Remote Similarity NPD506 Clinical (unspecified phase)
0.6259 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6259 Remote Similarity NPD9494 Approved
0.6258 Remote Similarity NPD7096 Clinical (unspecified phase)
0.625 Remote Similarity NPD1608 Approved
0.6233 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6232 Remote Similarity NPD3266 Approved
0.6232 Remote Similarity NPD3267 Approved
0.623 Remote Similarity NPD7798 Approved
0.6222 Remote Similarity NPD3026 Approved
0.6222 Remote Similarity NPD3023 Approved
0.6218 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6216 Remote Similarity NPD3750 Approved
0.6216 Remote Similarity NPD8166 Discontinued
0.6209 Remote Similarity NPD2649 Approved
0.6209 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6209 Remote Similarity NPD2651 Approved
0.6207 Remote Similarity NPD1510 Phase 2
0.6204 Remote Similarity NPD5159 Phase 2
0.6204 Remote Similarity NPD182 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5157 Phase 1
0.6204 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6203 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6202 Remote Similarity NPD969 Suspended
0.62 Remote Similarity NPD6799 Approved
0.6197 Remote Similarity NPD6663 Approved
0.6194 Remote Similarity NPD6280 Approved
0.6194 Remote Similarity NPD1245 Approved
0.6194 Remote Similarity NPD6279 Approved
0.619 Remote Similarity NPD1549 Phase 2
0.6187 Remote Similarity NPD6085 Phase 2
0.6187 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6187 Remote Similarity NPD1019 Discontinued
0.6184 Remote Similarity NPD920 Approved
0.6183 Remote Similarity NPD1246 Approved
0.6181 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6179 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6174 Remote Similarity NPD2354 Approved
0.6172 Remote Similarity NPD1756 Approved
0.6172 Remote Similarity NPD1752 Approved
0.6172 Remote Similarity NPD4234 Approved
0.6172 Remote Similarity NPD4233 Approved
0.6167 Remote Similarity NPD9260 Approved
0.6164 Remote Similarity NPD2531 Phase 2
0.6161 Remote Similarity NPD226 Approved
0.616 Remote Similarity NPD3047 Approved
0.616 Remote Similarity NPD3046 Approved
0.616 Remote Similarity NPD3048 Approved
0.6159 Remote Similarity NPD642 Clinical (unspecified phase)
0.6159 Remote Similarity NPD2532 Approved
0.6159 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6159 Remote Similarity NPD2534 Approved
0.6159 Remote Similarity NPD2533 Approved
0.6154 Remote Similarity NPD7819 Suspended
0.6154 Remote Similarity NPD2607 Approved
0.6149 Remote Similarity NPD1243 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