Structure

Physi-Chem Properties

Molecular Weight:  552.11
Volume:  539.112
LogP:  6.07
LogD:  2.474
LogS:  -4.584
# Rotatable Bonds:  5
TPSA:  159.8
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.204
Synthetic Accessibility Score:  2.872
Fsp3:  0.032
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.129
MDCK Permeability:  1.4835260117251892e-05
Pgp-inhibitor:  0.083
Pgp-substrate:  0.139
Human Intestinal Absorption (HIA):  0.17
20% Bioavailability (F20%):  0.97
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  96.66866302490234%
Volume Distribution (VD):  0.462
Pgp-substrate:  6.013087749481201%

ADMET: Metabolism

CYP1A2-inhibitor:  0.874
CYP1A2-substrate:  0.218
CYP2C19-inhibitor:  0.918
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.683
CYP2C9-substrate:  0.958
CYP2D6-inhibitor:  0.185
CYP2D6-substrate:  0.904
CYP3A4-inhibitor:  0.526
CYP3A4-substrate:  0.103

ADMET: Excretion

Clearance (CL):  4.312
Half-life (T1/2):  0.557

ADMET: Toxicity

hERG Blockers:  0.101
Human Hepatotoxicity (H-HT):  0.036
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.186
Rat Oral Acute Toxicity:  0.206
Maximum Recommended Daily Dose:  0.959
Skin Sensitization:  0.948
Carcinogencity:  0.094
Eye Corrosion:  0.003
Eye Irritation:  0.887
Respiratory Toxicity:  0.251

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

  Natural Product: NPC183

Natural Product ID:  NPC183
Common Name*:   2-[4-[5-(5,7-Dihydroxy-4-Oxochromen-2-Yl)-2-Methoxyphenoxy]Phenyl]-5,7-Dihydroxychromen-4-One
IUPAC Name:   2-[4-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenoxy]phenyl]-5,7-dihydroxychromen-4-one
Synonyms:  
Standard InCHIKey:  PRQWQWSKFNQAOG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C31H20O10/c1-38-24-7-4-16(26-14-23(37)31-21(35)10-18(33)12-29(31)41-26)8-27(24)39-19-5-2-15(3-6-19)25-13-22(36)30-20(34)9-17(32)11-28(30)40-25/h2-14,32-35H,1H3
SMILES:  COc1ccc(cc1Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL188147
PubChem CID:   5384799
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[11141124]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. leaf n.a. PMID[11735581]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15844965]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17602526]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5155 Peritassa compta Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5196 Eupatorium argentinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO471 Ardisia neriifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6729 Juniperus brevifolia Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3597 Rheedia acuminata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6237 Cryptocarya aschersoniana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 1.8 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition n.a. 1.2 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 12.1 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 2.9 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 0.1 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 1.6 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 13.0 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 0.9 uM PMID[463287]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition n.a. 14.8 uM PMID[463287]

☑ 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 NPC183 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
0.9735 High Similarity NPC112954
0.9675 High Similarity NPC272064
0.9545 High Similarity NPC34089
0.9545 High Similarity NPC196179
0.9542 High Similarity NPC190487
0.9542 High Similarity NPC154304
0.9484 High Similarity NPC219927
0.9481 High Similarity NPC188967
0.9477 High Similarity NPC183851
0.9477 High Similarity NPC63454
0.9463 High Similarity NPC195202
0.9419 High Similarity NPC66618
0.9419 High Similarity NPC288131
0.9419 High Similarity NPC84324
0.9419 High Similarity NPC305987
0.9419 High Similarity NPC165970
0.9419 High Similarity NPC113163
0.9416 High Similarity NPC172202
0.9416 High Similarity NPC284127
0.9416 High Similarity NPC476410
0.9396 High Similarity NPC12200
0.9396 High Similarity NPC62536
0.9396 High Similarity NPC33265
0.9363 High Similarity NPC477840
0.9359 High Similarity NPC477841
0.9355 High Similarity NPC101731
0.9338 High Similarity NPC219330
0.9338 High Similarity NPC50728
0.9338 High Similarity NPC166753
0.9308 High Similarity NPC475212
0.9276 High Similarity NPC308451
0.9276 High Similarity NPC208043
0.9276 High Similarity NPC226973
0.9276 High Similarity NPC236769
0.9276 High Similarity NPC76376
0.9272 High Similarity NPC183950
0.9272 High Similarity NPC177298
0.9272 High Similarity NPC287101
0.9272 High Similarity NPC137062
0.9272 High Similarity NPC159103
0.9272 High Similarity NPC52005
0.9272 High Similarity NPC223579
0.9272 High Similarity NPC48479
0.9272 High Similarity NPC328119
0.9226 High Similarity NPC185526
0.9221 High Similarity NPC138360
0.9221 High Similarity NPC280339
0.9221 High Similarity NPC92659
0.9221 High Similarity NPC167815
0.9221 High Similarity NPC201136
0.9221 High Similarity NPC146165
0.9221 High Similarity NPC196439
0.9221 High Similarity NPC128863
0.9221 High Similarity NPC2476
0.9221 High Similarity NPC50715
0.9221 High Similarity NPC183597
0.9221 High Similarity NPC227325
0.9221 High Similarity NPC163780
0.9221 High Similarity NPC4455
0.9216 High Similarity NPC60972
0.9216 High Similarity NPC39732
0.9211 High Similarity NPC306821
0.9205 High Similarity NPC261548
0.9205 High Similarity NPC120464
0.9198 High Similarity NPC99591
0.9172 High Similarity NPC158188
0.9161 High Similarity NPC178854
0.9161 High Similarity NPC471985
0.9156 High Similarity NPC179126
0.9156 High Similarity NPC176775
0.9156 High Similarity NPC145379
0.9156 High Similarity NPC231018
0.9156 High Similarity NPC22519
0.9156 High Similarity NPC276409
0.9156 High Similarity NPC194593
0.9156 High Similarity NPC303485
0.9156 High Similarity NPC58382
0.9156 High Similarity NPC71061
0.9156 High Similarity NPC274327
0.9156 High Similarity NPC162351
0.9156 High Similarity NPC86485
0.9156 High Similarity NPC270620
0.9156 High Similarity NPC255350
0.9156 High Similarity NPC250822
0.9156 High Similarity NPC69394
0.9156 High Similarity NPC78326
0.9156 High Similarity NPC47781
0.9156 High Similarity NPC246204
0.9156 High Similarity NPC75279
0.9156 High Similarity NPC236223
0.9156 High Similarity NPC160951
0.9156 High Similarity NPC183878
0.9156 High Similarity NPC72425
0.9156 High Similarity NPC290830
0.915 High Similarity NPC133953
0.915 High Similarity NPC252933
0.915 High Similarity NPC125062
0.915 High Similarity NPC200740
0.915 High Similarity NPC50403
0.915 High Similarity NPC54394
0.915 High Similarity NPC28274
0.9139 High Similarity NPC108406
0.913 High Similarity NPC476365
0.9128 High Similarity NPC9966
0.9128 High Similarity NPC70853
0.9125 High Similarity NPC295082
0.9125 High Similarity NPC243877
0.9119 High Similarity NPC58223
0.9119 High Similarity NPC7688
0.9119 High Similarity NPC7154
0.9119 High Similarity NPC125039
0.9119 High Similarity NPC72787
0.9119 High Similarity NPC36
0.9119 High Similarity NPC259757
0.9119 High Similarity NPC36916
0.9103 High Similarity NPC189179
0.9103 High Similarity NPC284820
0.9103 High Similarity NPC473272
0.9103 High Similarity NPC227192
0.9103 High Similarity NPC75215
0.9103 High Similarity NPC224137
0.9103 High Similarity NPC93376
0.9097 High Similarity NPC213622
0.9097 High Similarity NPC265624
0.9097 High Similarity NPC186227
0.9097 High Similarity NPC205026
0.9097 High Similarity NPC52611
0.9097 High Similarity NPC32557
0.9097 High Similarity NPC189960
0.9097 High Similarity NPC100049
0.9097 High Similarity NPC158027
0.9097 High Similarity NPC215203
0.9097 High Similarity NPC20830
0.9097 High Similarity NPC150908
0.9097 High Similarity NPC14606
0.9097 High Similarity NPC159707
0.9097 High Similarity NPC256612
0.9097 High Similarity NPC121649
0.9097 High Similarity NPC248739
0.9097 High Similarity NPC208197
0.9091 High Similarity NPC55205
0.9091 High Similarity NPC156222
0.9091 High Similarity NPC131624
0.9091 High Similarity NPC239128
0.9091 High Similarity NPC187498
0.9091 High Similarity NPC142540
0.9091 High Similarity NPC188203
0.9091 High Similarity NPC134677
0.9091 High Similarity NPC83508
0.9091 High Similarity NPC82325
0.9091 High Similarity NPC301323
0.9091 High Similarity NPC471982
0.9091 High Similarity NPC279989
0.9091 High Similarity NPC198826
0.9091 High Similarity NPC275722
0.9091 High Similarity NPC100887
0.9091 High Similarity NPC212678
0.9091 High Similarity NPC256283
0.9091 High Similarity NPC241498
0.9091 High Similarity NPC293183
0.9091 High Similarity NPC25270
0.9091 High Similarity NPC120163
0.9091 High Similarity NPC123886
0.9091 High Similarity NPC71334
0.9091 High Similarity NPC222830
0.9091 High Similarity NPC301123
0.9091 High Similarity NPC275836
0.9091 High Similarity NPC162313
0.9091 High Similarity NPC57030
0.9085 High Similarity NPC338131
0.9068 High Similarity NPC188079
0.9067 High Similarity NPC113089
0.9062 High Similarity NPC320741
0.9062 High Similarity NPC171985
0.906 High Similarity NPC29536
0.9051 High Similarity NPC26326
0.9051 High Similarity NPC40037
0.9051 High Similarity NPC142252
0.9045 High Similarity NPC143828
0.9045 High Similarity NPC19687
0.9045 High Similarity NPC280680
0.9045 High Similarity NPC7846
0.9045 High Similarity NPC18607
0.9045 High Similarity NPC184755
0.9045 High Similarity NPC4481
0.9045 High Similarity NPC204854
0.9045 High Similarity NPC288669
0.9045 High Similarity NPC152166
0.9045 High Similarity NPC74178
0.9045 High Similarity NPC25495
0.9045 High Similarity NPC261004
0.9045 High Similarity NPC55443
0.9045 High Similarity NPC18699
0.9045 High Similarity NPC105242
0.9045 High Similarity NPC130894
0.9045 High Similarity NPC300943
0.9045 High Similarity NPC191459
0.9045 High Similarity NPC9609
0.9045 High Similarity NPC18772
0.9045 High Similarity NPC176300

  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 NPC183 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
0.9156 High Similarity NPD2801 Approved
0.9119 High Similarity NPD6167 Clinical (unspecified phase)
0.9119 High Similarity NPD6168 Clinical (unspecified phase)
0.9119 High Similarity NPD6166 Phase 2
0.8968 High Similarity NPD1934 Approved
0.894 High Similarity NPD1511 Approved
0.8854 High Similarity NPD3817 Phase 2
0.8834 High Similarity NPD7054 Approved
0.8824 High Similarity NPD1512 Approved
0.879 High Similarity NPD2393 Clinical (unspecified phase)
0.878 High Similarity NPD7472 Approved
0.8679 High Similarity NPD3882 Suspended
0.8667 High Similarity NPD7074 Phase 3
0.8636 High Similarity NPD7410 Clinical (unspecified phase)
0.8636 High Similarity NPD4378 Clinical (unspecified phase)
0.8623 High Similarity NPD7808 Phase 3
0.8614 High Similarity NPD6797 Phase 2
0.858 High Similarity NPD6959 Discontinued
0.8563 High Similarity NPD7251 Discontinued
0.8562 High Similarity NPD4868 Clinical (unspecified phase)
0.8545 High Similarity NPD3818 Discontinued
0.8528 High Similarity NPD6232 Discontinued
0.8485 Intermediate Similarity NPD7473 Discontinued
0.8481 Intermediate Similarity NPD4380 Phase 2
0.8402 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7411 Suspended
0.8301 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD5494 Approved
0.8289 Intermediate Similarity NPD1510 Phase 2
0.8247 Intermediate Similarity NPD1549 Phase 2
0.8235 Intermediate Similarity NPD2796 Approved
0.8171 Intermediate Similarity NPD7075 Discontinued
0.8166 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8166 Intermediate Similarity NPD5844 Phase 1
0.816 Intermediate Similarity NPD5402 Approved
0.8146 Intermediate Similarity NPD1240 Approved
0.811 Intermediate Similarity NPD7768 Phase 2
0.8101 Intermediate Similarity NPD6799 Approved
0.8098 Intermediate Similarity NPD7819 Suspended
0.8063 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD5403 Approved
0.8039 Intermediate Similarity NPD1607 Approved
0.8037 Intermediate Similarity NPD6801 Discontinued
0.8036 Intermediate Similarity NPD3926 Phase 2
0.8013 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD1465 Phase 2
0.7988 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD7390 Discontinued
0.7952 Intermediate Similarity NPD3749 Approved
0.7937 Intermediate Similarity NPD5401 Approved
0.7911 Intermediate Similarity NPD3750 Approved
0.7816 Intermediate Similarity NPD6559 Discontinued
0.7811 Intermediate Similarity NPD1247 Approved
0.7809 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD6599 Discontinued
0.7798 Intermediate Similarity NPD919 Approved
0.7792 Intermediate Similarity NPD943 Approved
0.7764 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD447 Suspended
0.7736 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD7199 Phase 2
0.7662 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1551 Phase 2
0.7658 Intermediate Similarity NPD2935 Discontinued
0.7647 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD2800 Approved
0.7616 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD3748 Approved
0.7582 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD1613 Approved
0.7558 Intermediate Similarity NPD3787 Discontinued
0.7532 Intermediate Similarity NPD4908 Phase 1
0.753 Intermediate Similarity NPD3226 Approved
0.7528 Intermediate Similarity NPD8313 Approved
0.7528 Intermediate Similarity NPD8312 Approved
0.7516 Intermediate Similarity NPD1933 Approved
0.7516 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD2532 Approved
0.75 Intermediate Similarity NPD2534 Approved
0.75 Intermediate Similarity NPD2533 Approved
0.7486 Intermediate Similarity NPD3751 Discontinued
0.7484 Intermediate Similarity NPD3027 Phase 3
0.7469 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6651 Approved
0.7438 Intermediate Similarity NPD6100 Approved
0.7438 Intermediate Similarity NPD6099 Approved
0.7436 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD920 Approved
0.7407 Intermediate Similarity NPD1243 Approved
0.7396 Intermediate Similarity NPD37 Approved
0.7394 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD6234 Discontinued
0.7375 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4966 Approved
0.7368 Intermediate Similarity NPD4965 Approved
0.7368 Intermediate Similarity NPD4967 Phase 2
0.7366 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1653 Approved
0.7362 Intermediate Similarity NPD4628 Phase 3
0.736 Intermediate Similarity NPD5953 Discontinued
0.7338 Intermediate Similarity NPD1203 Approved
0.7325 Intermediate Similarity NPD2313 Discontinued
0.732 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD2309 Approved
0.7317 Intermediate Similarity NPD6190 Approved
0.7308 Intermediate Similarity NPD6832 Phase 2
0.7289 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD7228 Approved
0.7273 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3225 Approved
0.7267 Intermediate Similarity NPD1548 Phase 1
0.7267 Intermediate Similarity NPD2799 Discontinued
0.7253 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8455 Phase 2
0.7247 Intermediate Similarity NPD7286 Phase 2
0.7244 Intermediate Similarity NPD9494 Approved
0.7244 Intermediate Similarity NPD3018 Phase 2
0.7222 Intermediate Similarity NPD7685 Pre-registration
0.7222 Intermediate Similarity NPD5405 Approved
0.7222 Intermediate Similarity NPD5404 Approved
0.7222 Intermediate Similarity NPD5406 Approved
0.7222 Intermediate Similarity NPD5408 Approved
0.7219 Intermediate Similarity NPD7458 Discontinued
0.7216 Intermediate Similarity NPD8151 Discontinued
0.7215 Intermediate Similarity NPD3268 Approved
0.719 Intermediate Similarity NPD422 Phase 1
0.7188 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD7549 Discontinued
0.7179 Intermediate Similarity NPD2798 Approved
0.7178 Intermediate Similarity NPD2346 Discontinued
0.7175 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4360 Phase 2
0.7166 Intermediate Similarity NPD4363 Phase 3
0.716 Intermediate Similarity NPD7033 Discontinued
0.7158 Intermediate Similarity NPD6778 Approved
0.7158 Intermediate Similarity NPD6781 Approved
0.7158 Intermediate Similarity NPD6780 Approved
0.7158 Intermediate Similarity NPD6779 Approved
0.7158 Intermediate Similarity NPD6782 Approved
0.7158 Intermediate Similarity NPD6777 Approved
0.7158 Intermediate Similarity NPD6776 Approved
0.7152 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9717 Approved
0.7119 Intermediate Similarity NPD5242 Approved
0.7115 Intermediate Similarity NPD2797 Approved
0.7107 Intermediate Similarity NPD6798 Discontinued
0.7102 Intermediate Similarity NPD8127 Discontinued
0.7098 Intermediate Similarity NPD7870 Phase 2
0.7098 Intermediate Similarity NPD7871 Phase 2
0.7097 Intermediate Similarity NPD2982 Phase 2
0.7097 Intermediate Similarity NPD2983 Phase 2
0.7093 Intermediate Similarity NPD6844 Discontinued
0.7091 Intermediate Similarity NPD2654 Approved
0.7086 Intermediate Similarity NPD5536 Phase 2
0.7078 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD1610 Phase 2
0.7063 Intermediate Similarity NPD6233 Phase 2
0.7062 Intermediate Similarity NPD7229 Phase 3
0.7055 Intermediate Similarity NPD4308 Phase 3
0.7048 Intermediate Similarity NPD7003 Approved
0.7047 Intermediate Similarity NPD7696 Phase 3
0.7047 Intermediate Similarity NPD7698 Approved
0.7047 Intermediate Similarity NPD7697 Approved
0.7047 Intermediate Similarity NPD7435 Discontinued
0.7043 Intermediate Similarity NPD4287 Approved
0.7035 Intermediate Similarity NPD6386 Approved
0.7035 Intermediate Similarity NPD6385 Approved
0.7033 Intermediate Similarity NPD7038 Approved
0.7033 Intermediate Similarity NPD7039 Approved
0.7032 Intermediate Similarity NPD2981 Phase 2
0.7032 Intermediate Similarity NPD1608 Approved
0.7029 Intermediate Similarity NPD6971 Discontinued
0.7027 Intermediate Similarity NPD8150 Discontinued
0.7026 Intermediate Similarity NPD7584 Approved
0.7024 Intermediate Similarity NPD4357 Discontinued
0.7018 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD5353 Approved
0.7011 Intermediate Similarity NPD4288 Approved
0.7 Intermediate Similarity NPD7177 Discontinued
0.7 Intermediate Similarity NPD411 Approved
0.6983 Remote Similarity NPD2403 Approved
0.6982 Remote Similarity NPD7447 Phase 1
0.6975 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5124 Phase 1
0.697 Remote Similarity NPD7783 Phase 2
0.697 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1201 Approved
0.6966 Remote Similarity NPD5710 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