Structure

Physi-Chem Properties

Molecular Weight:  286.12
Volume:  302.181
LogP:  3.3
LogD:  3.58
LogS:  -4.459
# Rotatable Bonds:  5
TPSA:  47.92
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.853
Synthetic Accessibility Score:  1.999
Fsp3:  0.176
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.915
MDCK Permeability:  1.534333568997681e-05
Pgp-inhibitor:  0.917
Pgp-substrate:  0.283
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.649

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.157
Plasma Protein Binding (PPB):  95.73018646240234%
Volume Distribution (VD):  0.672
Pgp-substrate:  3.1817288398742676%

ADMET: Metabolism

CYP1A2-inhibitor:  0.979
CYP1A2-substrate:  0.947
CYP2C19-inhibitor:  0.773
CYP2C19-substrate:  0.44
CYP2C9-inhibitor:  0.219
CYP2C9-substrate:  0.944
CYP2D6-inhibitor:  0.4
CYP2D6-substrate:  0.933
CYP3A4-inhibitor:  0.908
CYP3A4-substrate:  0.437

ADMET: Excretion

Clearance (CL):  10.377
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.403
Human Hepatotoxicity (H-HT):  0.155
Drug-inuced Liver Injury (DILI):  0.845
AMES Toxicity:  0.366
Rat Oral Acute Toxicity:  0.021
Maximum Recommended Daily Dose:  0.328
Skin Sensitization:  0.933
Carcinogencity:  0.102
Eye Corrosion:  0.072
Eye Irritation:  0.966
Respiratory Toxicity:  0.146

Download Data

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

  Natural Product: NPC473411

Natural Product ID:  NPC473411
Common Name*:   Sid470675
IUPAC Name:   5-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-2-methoxyphenol
Synonyms:   NSC-381864
Standard InCHIKey:  UQIWTPQGJCCTPA-SNAWJCMRSA-N
Standard InCHI:  InChI=1S/C17H18O4/c1-19-14-8-13(9-15(11-14)20-2)5-4-12-6-7-17(21-3)16(18)10-12/h4-11,18H,1-3H3/b5-4+
SMILES:  COc1cc(/C=C/c2ccc(c(c2)O)OC)cc(c1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL419378
PubChem CID:   5385086
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes

*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
NPO88 Rheum undulatum Species Polygonaceae Eukaryota rhizome n.a. n.a. PMID[10714491]
NPO88 Rheum undulatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO88 Rheum undulatum Species Polygonaceae 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 = 700.0 nM PMID[476601]
NPT116 Cell Line HL-60 Homo sapiens AC50 = 900.0 nM PMID[476601]
NPT366 Individual Protein Quinone reductase 2 Homo sapiens IC50 = 15000.0 nM PMID[476604]
NPT886 Cell Line NIH3T3 Mus musculus IC50 = 200.0 nM PMID[476605]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 8511.38 nM PMID[476606]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 3435.58 nM PMID[476606]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 7516.23 nM PMID[476606]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 9462.37 nM PMID[476606]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 7709.03 nM PMID[476606]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1749.85 nM PMID[476606]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2393.32 nM PMID[476606]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 4178.3 nM PMID[476606]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 10023.05 nM PMID[476606]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 2432.2 nM PMID[476606]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 29376.5 nM PMID[476606]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 2162.72 nM PMID[476606]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 3349.65 nM PMID[476606]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 4197.59 nM PMID[476606]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 3917.42 nM PMID[476606]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 5915.62 nM PMID[476606]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 31768.74 nM PMID[476606]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 3872.58 nM PMID[476606]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 15205.48 nM PMID[476606]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 6412.1 nM PMID[476606]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 37325.02 nM PMID[476606]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 3819.44 nM PMID[476606]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 1690.44 nM PMID[476606]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 12387.97 nM PMID[476606]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 3083.19 nM PMID[476606]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 3372.87 nM PMID[476606]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 13645.83 nM PMID[476606]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 2192.8 nM PMID[476606]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 14321.88 nM PMID[476606]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 12189.9 nM PMID[476606]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 6412.1 nM PMID[476606]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 20370.42 nM PMID[476606]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 4819.48 nM PMID[476606]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 20323.57 nM PMID[476606]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 3935.5 nM PMID[476606]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 3404.08 nM PMID[476606]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 8550.67 nM PMID[476606]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 9660.51 nM PMID[476606]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 3326.6 nM PMID[476606]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 6025.6 nM PMID[476606]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 36057.86 nM PMID[476606]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 3155.0 nM PMID[476606]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 3647.54 nM PMID[476606]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 25468.3 nM PMID[476606]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 18749.95 nM PMID[476606]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 1958.84 nM PMID[476606]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 21183.61 nM PMID[476606]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 15703.63 nM PMID[476606]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 5636.38 nM PMID[476606]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 5861.38 nM PMID[476606]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 3155.0 nM PMID[476606]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 5520.77 nM PMID[476606]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 3451.44 nM PMID[476606]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 16749.43 nM PMID[476606]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 6081.35 nM PMID[476606]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 26485.0 nM PMID[476606]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1253.14 nM PMID[476606]
NPT886 Cell Line NIH3T3 Mus musculus IC50 = 210.0 nM PMID[476607]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 510.0 nM PMID[476607]
NPT579 Cell Line DLD-1 Homo sapiens IC50 = 210.0 nM PMID[476607]
NPT179 Cell Line A2780 Homo sapiens IC50 = 150.0 nM PMID[476607]
NPT81 Cell Line A549 Homo sapiens IC50 = 250.0 nM PMID[476607]
NPT81 Cell Line A549 Homo sapiens Activity = 78.0 % PMID[476607]
NPT1635 Cell Line H9c2 Rattus norvegicus Activity = 25.0 % PMID[476608]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 = 5490.0 nM PMID[476608]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 = 5480.0 nM PMID[476608]
NPT32 Organism Mus musculus Mus musculus IC50 = 23000.0 nM PMID[476602]
NPT176 Organism Artemia salina Artemia salina LC50 = 2.8 ppm PMID[476603]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 < 0.01 ug ml-1 PMID[476603]
NPT141 Organism Agrobacterium tumefaciens Agrobacterium tumefaciens Inhibition = 22.0 % PMID[476603]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. T/C = 119.0 % PMID[476603]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.1 ug ml-1 PMID[476603]
NPT935 Individual Protein Quinone reductase 1) Homo sapiens IC50 = 80000.0 nM PMID[476604]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 400.0 nM PMID[476607]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 830.0 nM PMID[476607]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 210.0 nM PMID[476607]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 220.0 nM PMID[476607]

☑ 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 NPC473411 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 NPC71579
1.0 High Similarity NPC262253
0.9826 High Similarity NPC166759
0.9746 High Similarity NPC475169
0.9746 High Similarity NPC221077
0.9746 High Similarity NPC233410
0.9746 High Similarity NPC251855
0.9746 High Similarity NPC117214
0.9746 High Similarity NPC82483
0.9746 High Similarity NPC265483
0.9746 High Similarity NPC116907
0.9746 High Similarity NPC193544
0.9746 High Similarity NPC208950
0.9746 High Similarity NPC472093
0.9746 High Similarity NPC299584
0.9746 High Similarity NPC298757
0.9746 High Similarity NPC57490
0.9746 High Similarity NPC17943
0.9746 High Similarity NPC203133
0.9739 High Similarity NPC474565
0.9739 High Similarity NPC232084
0.9739 High Similarity NPC247364
0.9739 High Similarity NPC10932
0.9739 High Similarity NPC61516
0.9664 High Similarity NPC78974
0.9664 High Similarity NPC223136
0.9664 High Similarity NPC18924
0.9664 High Similarity NPC103823
0.9664 High Similarity NPC44748
0.9664 High Similarity NPC28730
0.9664 High Similarity NPC214406
0.9652 High Similarity NPC226629
0.9583 High Similarity NPC246620
0.9583 High Similarity NPC124452
0.9583 High Similarity NPC74817
0.9583 High Similarity NPC236791
0.9583 High Similarity NPC159968
0.9583 High Similarity NPC293054
0.9583 High Similarity NPC82679
0.9583 High Similarity NPC282000
0.9583 High Similarity NPC169474
0.9583 High Similarity NPC210355
0.9583 High Similarity NPC127587
0.9583 High Similarity NPC324112
0.958 High Similarity NPC234400
0.958 High Similarity NPC60885
0.9576 High Similarity NPC228922
0.9576 High Similarity NPC233526
0.9576 High Similarity NPC197757
0.9576 High Similarity NPC95168
0.9576 High Similarity NPC136319
0.9576 High Similarity NPC282496
0.9504 High Similarity NPC470213
0.9504 High Similarity NPC186843
0.9504 High Similarity NPC98631
0.9504 High Similarity NPC206615
0.95 High Similarity NPC76451
0.9492 High Similarity NPC41562
0.9478 High Similarity NPC259638
0.9426 High Similarity NPC476968
0.9426 High Similarity NPC228769
0.9426 High Similarity NPC470633
0.9426 High Similarity NPC10225
0.9426 High Similarity NPC170844
0.9426 High Similarity NPC58164
0.9417 High Similarity NPC105925
0.9407 High Similarity NPC145780
0.9407 High Similarity NPC75713
0.9402 High Similarity NPC229401
0.9391 High Similarity NPC193067
0.9391 High Similarity NPC123948
0.935 High Similarity NPC234488
0.935 High Similarity NPC311680
0.935 High Similarity NPC299221
0.935 High Similarity NPC472338
0.935 High Similarity NPC126836
0.935 High Similarity NPC51840
0.9344 High Similarity NPC28765
0.9344 High Similarity NPC154866
0.9333 High Similarity NPC5796
0.9333 High Similarity NPC122792
0.9333 High Similarity NPC228972
0.9333 High Similarity NPC206487
0.9316 High Similarity NPC20674
0.9274 High Similarity NPC472597
0.9274 High Similarity NPC470095
0.9274 High Similarity NPC470096
0.9274 High Similarity NPC474017
0.9268 High Similarity NPC212015
0.9262 High Similarity NPC470699
0.9262 High Similarity NPC252131
0.9262 High Similarity NPC266555
0.9262 High Similarity NPC236760
0.925 High Similarity NPC121115
0.925 High Similarity NPC84086
0.9244 High Similarity NPC49341
0.9217 High Similarity NPC228287
0.9217 High Similarity NPC180508
0.92 High Similarity NPC6451
0.92 High Similarity NPC35932
0.92 High Similarity NPC184447
0.92 High Similarity NPC7903
0.92 High Similarity NPC253105
0.92 High Similarity NPC201587
0.92 High Similarity NPC16208
0.92 High Similarity NPC160991
0.9194 High Similarity NPC214860
0.9187 High Similarity NPC266691
0.918 High Similarity NPC223953
0.918 High Similarity NPC181361
0.9174 High Similarity NPC183446
0.9153 High Similarity NPC475961
0.9153 High Similarity NPC254625
0.9127 High Similarity NPC229442
0.9127 High Similarity NPC158331
0.9127 High Similarity NPC36661
0.9127 High Similarity NPC32778
0.9127 High Similarity NPC471391
0.9127 High Similarity NPC168059
0.9127 High Similarity NPC475840
0.9127 High Similarity NPC471390
0.912 High Similarity NPC12275
0.912 High Similarity NPC232275
0.912 High Similarity NPC474356
0.912 High Similarity NPC45715
0.9113 High Similarity NPC285339
0.9113 High Similarity NPC190629
0.9113 High Similarity NPC202582
0.9113 High Similarity NPC45824
0.9113 High Similarity NPC470258
0.9113 High Similarity NPC3439
0.9113 High Similarity NPC210623
0.9113 High Similarity NPC218856
0.9113 High Similarity NPC226788
0.9113 High Similarity NPC222004
0.9113 High Similarity NPC273295
0.9106 High Similarity NPC474119
0.9091 High Similarity NPC471693
0.9091 High Similarity NPC220598
0.9091 High Similarity NPC165375
0.9091 High Similarity NPC238810
0.9068 High Similarity NPC470626
0.9055 High Similarity NPC111635
0.9055 High Similarity NPC310854
0.9055 High Similarity NPC317380
0.9055 High Similarity NPC287745
0.9055 High Similarity NPC170694
0.9048 High Similarity NPC86655
0.9048 High Similarity NPC14224
0.9048 High Similarity NPC161958
0.9048 High Similarity NPC202762
0.9048 High Similarity NPC204215
0.9048 High Similarity NPC127624
0.9048 High Similarity NPC175067
0.9048 High Similarity NPC470752
0.9043 High Similarity NPC280606
0.904 High Similarity NPC91291
0.904 High Similarity NPC192687
0.904 High Similarity NPC224157
0.904 High Similarity NPC63574
0.9 High Similarity NPC472596
0.9 High Similarity NPC199023
0.8984 High Similarity NPC99572
0.8984 High Similarity NPC10314
0.8984 High Similarity NPC94750
0.8984 High Similarity NPC474206
0.8984 High Similarity NPC313081
0.8984 High Similarity NPC472337
0.8984 High Similarity NPC470356
0.8984 High Similarity NPC126409
0.8984 High Similarity NPC69029
0.8984 High Similarity NPC121812
0.8984 High Similarity NPC112246
0.8984 High Similarity NPC112939
0.8984 High Similarity NPC294884
0.8984 High Similarity NPC200557
0.8984 High Similarity NPC158142
0.8984 High Similarity NPC108198
0.8984 High Similarity NPC256262
0.8983 High Similarity NPC293619
0.8983 High Similarity NPC474933
0.8976 High Similarity NPC36490
0.8968 High Similarity NPC15543
0.8968 High Similarity NPC469625
0.8968 High Similarity NPC30043
0.8968 High Similarity NPC309787
0.8968 High Similarity NPC469613
0.896 High Similarity NPC469963
0.896 High Similarity NPC469951
0.896 High Similarity NPC190144
0.8957 High Similarity NPC203924
0.8957 High Similarity NPC296920
0.8957 High Similarity NPC90520
0.8952 High Similarity NPC118533
0.8952 High Similarity NPC242032
0.8952 High Similarity NPC165045
0.8952 High Similarity NPC319625
0.8952 High Similarity NPC163332
0.8952 High Similarity NPC41706
0.8952 High Similarity NPC216836

  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 NPC473411 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
0.9426 High Similarity NPD3027 Phase 3
0.8934 High Similarity NPD2983 Phase 2
0.8934 High Similarity NPD2982 Phase 2
0.8852 High Similarity NPD2981 Phase 2
0.873 High Similarity NPD1529 Clinical (unspecified phase)
0.8651 High Similarity NPD3018 Phase 2
0.8651 High Similarity NPD1530 Clinical (unspecified phase)
0.8632 High Similarity NPD228 Approved
0.8629 High Similarity NPD4379 Clinical (unspecified phase)
0.8605 High Similarity NPD1612 Clinical (unspecified phase)
0.8605 High Similarity NPD1613 Approved
0.8333 Intermediate Similarity NPD5283 Phase 1
0.8087 Intermediate Similarity NPD1242 Phase 1
0.8065 Intermediate Similarity NPD5536 Phase 2
0.8015 Intermediate Similarity NPD4908 Phase 1
0.8 Intermediate Similarity NPD4357 Discontinued
0.8 Intermediate Similarity NPD3021 Approved
0.8 Intermediate Similarity NPD3022 Approved
0.8 Intermediate Similarity NPD1548 Phase 1
0.7956 Intermediate Similarity NPD3540 Phase 1
0.791 Intermediate Similarity NPD1558 Phase 1
0.7895 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD1610 Phase 2
0.7883 Intermediate Similarity NPD3539 Phase 1
0.7877 Intermediate Similarity NPD2801 Approved
0.7808 Intermediate Similarity NPD1934 Approved
0.7795 Intermediate Similarity NPD1357 Approved
0.777 Intermediate Similarity NPD3882 Suspended
0.7687 Intermediate Similarity NPD4625 Phase 3
0.7671 Intermediate Similarity NPD4678 Approved
0.7671 Intermediate Similarity NPD4675 Approved
0.7655 Intermediate Similarity NPD1653 Approved
0.7652 Intermediate Similarity NPD9296 Approved
0.7647 Intermediate Similarity NPD3620 Phase 2
0.7647 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD4749 Approved
0.763 Intermediate Similarity NPD3144 Approved
0.763 Intermediate Similarity NPD3145 Approved
0.7622 Intermediate Similarity NPD1511 Approved
0.7615 Intermediate Similarity NPD3705 Approved
0.7606 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD2219 Phase 1
0.7589 Intermediate Similarity NPD3060 Approved
0.7574 Intermediate Similarity NPD2674 Phase 3
0.7552 Intermediate Similarity NPD7124 Phase 2
0.755 Intermediate Similarity NPD6234 Discontinued
0.7537 Intermediate Similarity NPD9494 Approved
0.7517 Intermediate Similarity NPD1512 Approved
0.75 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4005 Discontinued
0.7481 Intermediate Similarity NPD422 Phase 1
0.748 Intermediate Similarity NPD2684 Approved
0.7464 Intermediate Similarity NPD230 Phase 1
0.7463 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD37 Approved
0.7447 Intermediate Similarity NPD7266 Discontinued
0.7419 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6166 Phase 2
0.7417 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD940 Approved
0.7417 Intermediate Similarity NPD846 Approved
0.7407 Intermediate Similarity NPD2861 Phase 2
0.7391 Intermediate Similarity NPD4060 Phase 1
0.7381 Intermediate Similarity NPD7843 Approved
0.7379 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD6111 Discontinued
0.7351 Intermediate Similarity NPD3817 Phase 2
0.735 Intermediate Similarity NPD2933 Approved
0.735 Intermediate Similarity NPD2934 Approved
0.7348 Intermediate Similarity NPD1091 Approved
0.7347 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD7157 Approved
0.7343 Intermediate Similarity NPD4237 Approved
0.7343 Intermediate Similarity NPD4236 Phase 3
0.7329 Intermediate Similarity NPD4123 Phase 3
0.7317 Intermediate Similarity NPD968 Approved
0.7313 Intermediate Similarity NPD2922 Phase 1
0.7303 Intermediate Similarity NPD4965 Approved
0.7303 Intermediate Similarity NPD4966 Approved
0.7303 Intermediate Similarity NPD4967 Phase 2
0.729 Intermediate Similarity NPD6232 Discontinued
0.7288 Intermediate Similarity NPD2860 Approved
0.7288 Intermediate Similarity NPD2859 Approved
0.728 Intermediate Similarity NPD4750 Phase 3
0.7278 Intermediate Similarity NPD7054 Approved
0.7273 Intermediate Similarity NPD291 Approved
0.7266 Intermediate Similarity NPD1240 Approved
0.726 Intermediate Similarity NPD5297 Approved
0.7258 Intermediate Similarity NPD290 Approved
0.7255 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD3020 Approved
0.7246 Intermediate Similarity NPD5111 Phase 2
0.7246 Intermediate Similarity NPD5109 Approved
0.7246 Intermediate Similarity NPD5110 Phase 2
0.7241 Intermediate Similarity NPD6190 Approved
0.7233 Intermediate Similarity NPD7074 Phase 3
0.7233 Intermediate Similarity NPD7472 Approved
0.7226 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD7199 Phase 2
0.7215 Intermediate Similarity NPD3818 Discontinued
0.7215 Intermediate Similarity NPD7228 Approved
0.7209 Intermediate Similarity NPD6671 Approved
0.7206 Intermediate Similarity NPD6584 Phase 3
0.7183 Intermediate Similarity NPD1510 Phase 2
0.7174 Intermediate Similarity NPD7095 Approved
0.7171 Intermediate Similarity NPD2977 Approved
0.7171 Intermediate Similarity NPD2978 Approved
0.7163 Intermediate Similarity NPD1607 Approved
0.7162 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7473 Discontinued
0.7143 Intermediate Similarity NPD943 Approved
0.7143 Intermediate Similarity NPD4055 Discovery
0.7143 Intermediate Similarity NPD5451 Approved
0.7134 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD9094 Approved
0.7124 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD5718 Phase 2
0.712 Intermediate Similarity NPD1358 Approved
0.7113 Intermediate Similarity NPD4538 Approved
0.7113 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD4536 Approved
0.7103 Intermediate Similarity NPD5177 Phase 3
0.7103 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4162 Approved
0.7095 Intermediate Similarity NPD7447 Phase 1
0.7095 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4380 Phase 2
0.7083 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6797 Phase 2
0.707 Intermediate Similarity NPD4606 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD5846 Approved
0.7068 Intermediate Similarity NPD6516 Phase 2
0.7059 Intermediate Similarity NPD8651 Approved
0.7059 Intermediate Similarity NPD1465 Phase 2
0.7047 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7251 Discontinued
0.7034 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD7213 Phase 3
0.7027 Intermediate Similarity NPD6799 Approved
0.7027 Intermediate Similarity NPD7212 Phase 2
0.7021 Intermediate Similarity NPD2238 Phase 2
0.7015 Intermediate Similarity NPD3847 Discontinued
0.7014 Intermediate Similarity NPD2935 Discontinued
0.7014 Intermediate Similarity NPD6100 Approved
0.7014 Intermediate Similarity NPD6099 Approved
0.7012 Intermediate Similarity NPD8053 Approved
0.7012 Intermediate Similarity NPD8054 Approved
0.7007 Intermediate Similarity NPD5241 Discontinued
0.6994 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7808 Phase 3
0.6993 Remote Similarity NPD6896 Approved
0.6993 Remote Similarity NPD6895 Approved
0.6986 Remote Similarity NPD6674 Discontinued
0.6986 Remote Similarity NPD1652 Phase 2
0.6985 Remote Similarity NPD6582 Phase 2
0.6985 Remote Similarity NPD6583 Phase 3
0.698 Remote Similarity NPD1424 Approved
0.6977 Remote Similarity NPD5535 Approved
0.6972 Remote Similarity NPD4340 Discontinued
0.697 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1375 Discontinued
0.6966 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5844 Phase 1
0.695 Remote Similarity NPD6233 Phase 2
0.695 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5588 Approved
0.6944 Remote Similarity NPD5960 Phase 3
0.694 Remote Similarity NPD4626 Approved
0.694 Remote Similarity NPD2668 Approved
0.694 Remote Similarity NPD2667 Approved
0.6939 Remote Similarity NPD3892 Phase 2
0.6939 Remote Similarity NPD6331 Phase 2
0.6939 Remote Similarity NPD3750 Approved
0.6939 Remote Similarity NPD4628 Phase 3
0.6939 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6939 Remote Similarity NPD4110 Phase 3
0.6928 Remote Similarity NPD5089 Approved
0.6928 Remote Similarity NPD5090 Approved
0.6923 Remote Similarity NPD7075 Discontinued
0.6918 Remote Similarity NPD1549 Phase 2
0.6917 Remote Similarity NPD7533 Approved
0.6917 Remote Similarity NPD7534 Approved
0.6912 Remote Similarity NPD1608 Approved
0.6912 Remote Similarity NPD2230 Approved
0.6912 Remote Similarity NPD9269 Phase 2
0.6912 Remote Similarity NPD2233 Approved
0.6912 Remote Similarity NPD2232 Approved
0.6909 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6905 Remote Similarity NPD3134 Approved
0.6901 Remote Similarity NPD3062 Approved
0.6901 Remote Similarity NPD3059 Approved
0.6901 Remote Similarity NPD3061 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