Structure

Physi-Chem Properties

Molecular Weight:  552.11
Volume:  539.112
LogP:  6.332
LogD:  2.437
LogS:  -4.444
# Rotatable Bonds:  4
TPSA:  170.8
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.19
Synthetic Accessibility Score:  2.989
Fsp3:  0.032
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.199
MDCK Permeability:  9.413808584213257e-06
Pgp-inhibitor:  0.087
Pgp-substrate:  0.049
Human Intestinal Absorption (HIA):  0.534
20% Bioavailability (F20%):  0.931
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  96.4674072265625%
Volume Distribution (VD):  0.471
Pgp-substrate:  5.151566982269287%

ADMET: Metabolism

CYP1A2-inhibitor:  0.879
CYP1A2-substrate:  0.194
CYP2C19-inhibitor:  0.751
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.568
CYP2C9-substrate:  0.928
CYP2D6-inhibitor:  0.084
CYP2D6-substrate:  0.859
CYP3A4-inhibitor:  0.19
CYP3A4-substrate:  0.078

ADMET: Excretion

Clearance (CL):  3.659
Half-life (T1/2):  0.286

ADMET: Toxicity

hERG Blockers:  0.061
Human Hepatotoxicity (H-HT):  0.17
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.252
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.885
Skin Sensitization:  0.848
Carcinogencity:  0.039
Eye Corrosion:  0.003
Eye Irritation:  0.885
Respiratory Toxicity:  0.058

Download Data

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

  Natural Product: NPC303485

Natural Product ID:  NPC303485
Common Name*:   Podocarpusflavone A
IUPAC Name:   8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  RBTRUVNXLDXHBJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C31H20O10/c1-39-17-5-2-14(3-6-17)25-13-24(38)30-22(36)11-21(35)28(31(30)41-25)18-8-15(4-7-19(18)33)26-12-23(37)29-20(34)9-16(32)10-27(29)40-26/h2-13,32-36H,1H3
SMILES:  COc1ccc(cc1)c1cc(=O)c2c(o1)c(c(cc2O)O)c1cc(ccc1O)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL220745
PubChem CID:   5320644
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
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(01)00320-X]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. leaf n.a. PMID[11738417]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[15620255]
NPO22706 Aglaia forbesii Species Meliaceae Eukaryota n.a. leaf n.a. PMID[17707871]
NPO21757 Selaginella moellendorfii Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[19422203]
NPO21789 Sciadotenia toxifera Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[20961068]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. fruit n.a. PMID[21462031]
NPO29798 Podocarpus imbricatus Species Podocarpaceae Eukaryota twigs and leaves n.a. n.a. PMID[24953598]
NPO21757 Selaginella moellendorfii Species Selaginellaceae Eukaryota Whole Plants n.a. n.a. PMID[29412669]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota Twigs n.a. n.a. PMID[32786878]
NPO21757 Selaginella moellendorfii Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[9134745]
NPO28364 Zanthoxylum podocarpum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20900 Dendrobium chrysotoxum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29798 Podocarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21757 Selaginella moellendorfii Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20900 Dendrobium chrysotoxum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21757 Selaginella moellendorfii Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28364 Zanthoxylum podocarpum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20900 Dendrobium chrysotoxum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22567 Ectatosoma tiaratum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25305 Penicillium toxicarium Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22892 Valeriana microphylla Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22446 Caloplaca murorum Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28364 Zanthoxylum podocarpum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21757 Selaginella moellendorfii Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22960 Hydnocarpus hainanensis Species Achariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16299 Nitraria sibirica Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20900 Dendrobium chrysotoxum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21789 Sciadotenia toxifera Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22706 Aglaia forbesii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20778 Pinus longifolia Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20588 Soulamea pancheri Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11289 Eurybia divaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20385 Quercus canariensis Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4527 Coprinellus heptemerus Species Psathyrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14252 Erythrophyllum delesserioides Species Kallymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20287 Passalora fulva Species Mycosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11624 Didymella lethalis Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae 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
NPT3595 Individual Protein Cathepsin K Homo sapiens IC50 = 1.39 ug.mL-1 PMID[479514]
NPT81 Cell Line A549 Homo sapiens IC50 = 1.6 ug.mL-1 PMID[479514]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 1.6 ug.mL-1 PMID[479514]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 1.6 ug.mL-1 PMID[479514]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 1.6 ug.mL-1 PMID[479514]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 1.6 ug.mL-1 PMID[479514]
NPT319 Cell Line B16 Mus musculus IC50 = 1.6 ug.mL-1 PMID[479514]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 7900.0 nM PMID[479519]
NPT4717 Individual Protein Cystathionine beta-synthase Homo sapiens IC50 = 8900.0 nM PMID[479519]
NPT27 Others Unspecified IC50 = 1.6 ug.mL-1 PMID[479514]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 = 990.0 nM PMID[479516]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 > 100000.0 nM PMID[479517]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 49.3 % PMID[479518]
NPT2 Others Unspecified IC50 = 19000.0 nM PMID[479519]
NPT2 Others Unspecified Ratio IC50 = 10.0 n.a. PMID[479519]
NPT24914 SINGLE PROTEIN Cystathionine gamma-lyase Homo sapiens IC50 > 400000.0 nM PMID[479519]
NPT78 Individual Protein Beta amyloid A4 protein Homo sapiens IC50 = 4900.0 nM PMID[479520]

☑ 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 NPC303485 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 NPC71061
1.0 High Similarity NPC72425
1.0 High Similarity NPC290830
1.0 High Similarity NPC194593
0.9932 High Similarity NPC158027
0.9932 High Similarity NPC265624
0.9932 High Similarity NPC52611
0.9932 High Similarity NPC100049
0.9932 High Similarity NPC159707
0.9932 High Similarity NPC186227
0.9932 High Similarity NPC121649
0.9932 High Similarity NPC248739
0.9932 High Similarity NPC14606
0.9932 High Similarity NPC150908
0.9932 High Similarity NPC215203
0.9932 High Similarity NPC205026
0.9863 High Similarity NPC222713
0.9863 High Similarity NPC67322
0.9863 High Similarity NPC138299
0.9863 High Similarity NPC111112
0.9664 High Similarity NPC182555
0.9664 High Similarity NPC66441
0.9603 High Similarity NPC18699
0.9603 High Similarity NPC55443
0.9592 High Similarity NPC288840
0.9592 High Similarity NPC291746
0.9539 High Similarity NPC186325
0.9533 High Similarity NPC134171
0.9533 High Similarity NPC254351
0.9533 High Similarity NPC300668
0.9477 High Similarity NPC273467
0.9477 High Similarity NPC189552
0.9474 High Similarity NPC51760
0.9474 High Similarity NPC177650
0.947 High Similarity NPC32867
0.9412 High Similarity NPC312993
0.9412 High Similarity NPC121647
0.9408 High Similarity NPC475184
0.94 High Similarity NPC174086
0.9346 High Similarity NPC295090
0.9342 High Similarity NPC56049
0.9342 High Similarity NPC69531
0.9342 High Similarity NPC54830
0.9338 High Similarity NPC324447
0.9329 High Similarity NPC3642
0.9295 High Similarity NPC469664
0.9281 High Similarity NPC257166
0.9281 High Similarity NPC1796
0.9262 High Similarity NPC122894
0.9262 High Similarity NPC244407
0.9247 High Similarity NPC14871
0.9247 High Similarity NPC26238
0.9226 High Similarity NPC312273
0.9226 High Similarity NPC301256
0.9221 High Similarity NPC15815
0.9221 High Similarity NPC51247
0.9221 High Similarity NPC105584
0.9216 High Similarity NPC61112
0.9216 High Similarity NPC198489
0.9211 High Similarity NPC121568
0.92 High Similarity NPC5173
0.9195 High Similarity NPC14001
0.9195 High Similarity NPC97716
0.9195 High Similarity NPC261271
0.9195 High Similarity NPC24673
0.9195 High Similarity NPC475348
0.9195 High Similarity NPC166757
0.9195 High Similarity NPC237635
0.9195 High Similarity NPC201731
0.9195 High Similarity NPC104406
0.9195 High Similarity NPC79469
0.9189 High Similarity NPC319752
0.9189 High Similarity NPC273538
0.9189 High Similarity NPC278175
0.9189 High Similarity NPC282957
0.9189 High Similarity NPC194949
0.9189 High Similarity NPC216538
0.9189 High Similarity NPC257236
0.9184 High Similarity NPC299080
0.9184 High Similarity NPC78803
0.9184 High Similarity NPC62840
0.9184 High Similarity NPC214236
0.9184 High Similarity NPC293852
0.9184 High Similarity NPC59739
0.9184 High Similarity NPC217083
0.9178 High Similarity NPC241100
0.9178 High Similarity NPC159275
0.9172 High Similarity NPC259757
0.9167 High Similarity NPC473012
0.9161 High Similarity NPC98023
0.9161 High Similarity NPC42965
0.9161 High Similarity NPC226462
0.9161 High Similarity NPC195136
0.9156 High Similarity NPC271741
0.9156 High Similarity NPC183
0.9156 High Similarity NPC287789
0.915 High Similarity NPC258474
0.915 High Similarity NPC201227
0.915 High Similarity NPC79375
0.915 High Similarity NPC37253
0.9145 High Similarity NPC208011
0.9145 High Similarity NPC115601
0.9145 High Similarity NPC39154
0.9145 High Similarity NPC78324
0.9139 High Similarity NPC29777
0.9139 High Similarity NPC471115
0.9133 High Similarity NPC152233
0.9133 High Similarity NPC161191
0.9133 High Similarity NPC6511
0.9133 High Similarity NPC321623
0.9133 High Similarity NPC189087
0.9133 High Similarity NPC266572
0.9133 High Similarity NPC296869
0.9128 High Similarity NPC220418
0.9128 High Similarity NPC473078
0.9128 High Similarity NPC178343
0.9128 High Similarity NPC306488
0.9128 High Similarity NPC474161
0.9128 High Similarity NPC470132
0.9128 High Similarity NPC109183
0.9128 High Similarity NPC228779
0.9128 High Similarity NPC476088
0.9128 High Similarity NPC470133
0.9128 High Similarity NPC5820
0.9128 High Similarity NPC124729
0.9128 High Similarity NPC470134
0.9128 High Similarity NPC470131
0.9122 High Similarity NPC212932
0.9122 High Similarity NPC190637
0.9122 High Similarity NPC9117
0.9122 High Similarity NPC24821
0.9122 High Similarity NPC11700
0.9122 High Similarity NPC219915
0.9122 High Similarity NPC293053
0.9116 High Similarity NPC282300
0.9116 High Similarity NPC110969
0.911 High Similarity NPC220062
0.911 High Similarity NPC78913
0.911 High Similarity NPC96565
0.911 High Similarity NPC53181
0.911 High Similarity NPC303633
0.911 High Similarity NPC18260
0.911 High Similarity NPC217186
0.911 High Similarity NPC216978
0.911 High Similarity NPC301217
0.911 High Similarity NPC55018
0.9108 High Similarity NPC473009
0.9108 High Similarity NPC38591
0.9103 High Similarity NPC18380
0.9097 High Similarity NPC90497
0.9097 High Similarity NPC123544
0.9091 High Similarity NPC192587
0.9091 High Similarity NPC309648
0.9085 High Similarity NPC329844
0.9079 High Similarity NPC178484
0.9067 High Similarity NPC296998
0.9067 High Similarity NPC473077
0.9067 High Similarity NPC308200
0.906 High Similarity NPC470136
0.906 High Similarity NPC311741
0.906 High Similarity NPC470135
0.906 High Similarity NPC271288
0.906 High Similarity NPC326500
0.906 High Similarity NPC39045
0.906 High Similarity NPC234629
0.906 High Similarity NPC224714
0.9054 High Similarity NPC473042
0.9054 High Similarity NPC226636
0.9054 High Similarity NPC200694
0.9054 High Similarity NPC11561
0.9051 High Similarity NPC473010
0.9048 High Similarity NPC261227
0.9048 High Similarity NPC172986
0.9048 High Similarity NPC270883
0.9048 High Similarity NPC150522
0.9045 High Similarity NPC15374
0.9045 High Similarity NPC473011
0.9041 High Similarity NPC251681
0.9041 High Similarity NPC201395
0.9041 High Similarity NPC243528
0.9038 High Similarity NPC292863
0.9038 High Similarity NPC184326
0.9032 High Similarity NPC324358
0.9032 High Similarity NPC318527
0.9032 High Similarity NPC65504
0.9032 High Similarity NPC322459
0.9032 High Similarity NPC323627
0.9032 High Similarity NPC208258
0.9026 High Similarity NPC470681
0.902 High Similarity NPC161881
0.902 High Similarity NPC10807
0.902 High Similarity NPC43345
0.902 High Similarity NPC150123
0.902 High Similarity NPC56232
0.902 High Similarity NPC244583
0.9013 High Similarity NPC321896
0.9013 High Similarity NPC151973
0.9013 High Similarity NPC476185
0.9013 High Similarity NPC472633
0.9013 High Similarity NPC188403

  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 NPC303485 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
0.9189 High Similarity NPD7410 Clinical (unspecified phase)
0.9189 High Similarity NPD4378 Clinical (unspecified phase)
0.9103 High Similarity NPD6959 Discontinued
0.9051 High Similarity NPD7852 Clinical (unspecified phase)
0.9026 High Similarity NPD8443 Clinical (unspecified phase)
0.8846 High Similarity NPD7768 Phase 2
0.8831 High Similarity NPD7411 Suspended
0.8766 High Similarity NPD4380 Phase 2
0.8599 High Similarity NPD2393 Clinical (unspecified phase)
0.8591 High Similarity NPD1552 Clinical (unspecified phase)
0.8591 High Similarity NPD1550 Clinical (unspecified phase)
0.8581 High Similarity NPD1510 Phase 2
0.8533 High Similarity NPD1549 Phase 2
0.8523 High Similarity NPD2796 Approved
0.8497 Intermediate Similarity NPD7390 Discontinued
0.8481 Intermediate Similarity NPD7819 Suspended
0.8466 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD6166 Phase 2
0.8438 Intermediate Similarity NPD7075 Discontinued
0.8438 Intermediate Similarity NPD3749 Approved
0.8438 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8435 Intermediate Similarity NPD1240 Approved
0.8424 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8377 Intermediate Similarity NPD1511 Approved
0.8365 Intermediate Similarity NPD2801 Approved
0.8344 Intermediate Similarity NPD6232 Discontinued
0.8322 Intermediate Similarity NPD1607 Approved
0.8303 Intermediate Similarity NPD7473 Discontinued
0.8302 Intermediate Similarity NPD1934 Approved
0.8302 Intermediate Similarity NPD6801 Discontinued
0.8301 Intermediate Similarity NPD3750 Approved
0.8269 Intermediate Similarity NPD1512 Approved
0.825 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD2800 Approved
0.8235 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD7054 Approved
0.8086 Intermediate Similarity NPD3817 Phase 2
0.8054 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD7074 Phase 3
0.8047 Intermediate Similarity NPD7472 Approved
0.8037 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6799 Approved
0.8 Intermediate Similarity NPD1243 Approved
0.8 Intermediate Similarity NPD5494 Approved
0.8 Intermediate Similarity NPD6797 Phase 2
0.7988 Intermediate Similarity NPD5844 Phase 1
0.7987 Intermediate Similarity NPD920 Approved
0.7987 Intermediate Similarity NPD5403 Approved
0.7987 Intermediate Similarity NPD2344 Approved
0.7974 Intermediate Similarity NPD3748 Approved
0.7961 Intermediate Similarity NPD6651 Approved
0.7953 Intermediate Similarity NPD6559 Discontinued
0.7953 Intermediate Similarity NPD7251 Discontinued
0.795 Intermediate Similarity NPD6599 Discontinued
0.7929 Intermediate Similarity NPD3818 Discontinued
0.7927 Intermediate Similarity NPD3882 Suspended
0.7922 Intermediate Similarity NPD2935 Discontinued
0.7919 Intermediate Similarity NPD4908 Phase 1
0.7907 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD7808 Phase 3
0.7895 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD3226 Approved
0.7866 Intermediate Similarity NPD5402 Approved
0.7862 Intermediate Similarity NPD2532 Approved
0.7862 Intermediate Similarity NPD2534 Approved
0.7862 Intermediate Similarity NPD5401 Approved
0.7862 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD2533 Approved
0.7857 Intermediate Similarity NPD2799 Discontinued
0.7848 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD2313 Discontinued
0.7806 Intermediate Similarity NPD1551 Phase 2
0.7791 Intermediate Similarity NPD5953 Discontinued
0.7785 Intermediate Similarity NPD2309 Approved
0.7742 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7003 Approved
0.7701 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD8455 Phase 2
0.7692 Intermediate Similarity NPD5408 Approved
0.7692 Intermediate Similarity NPD5405 Approved
0.7692 Intermediate Similarity NPD5406 Approved
0.7692 Intermediate Similarity NPD5404 Approved
0.7674 Intermediate Similarity NPD7286 Phase 2
0.7667 Intermediate Similarity NPD4363 Phase 3
0.7667 Intermediate Similarity NPD4360 Phase 2
0.7657 Intermediate Similarity NPD8313 Approved
0.7657 Intermediate Similarity NPD8312 Approved
0.7647 Intermediate Similarity NPD3926 Phase 2
0.764 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD1465 Phase 2
0.7582 Intermediate Similarity NPD3268 Approved
0.7582 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD6100 Approved
0.758 Intermediate Similarity NPD6099 Approved
0.7561 Intermediate Similarity NPD7458 Discontinued
0.7556 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD2798 Approved
0.7532 Intermediate Similarity NPD2346 Discontinued
0.7531 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD1247 Approved
0.7515 Intermediate Similarity NPD919 Approved
0.75 Intermediate Similarity NPD4628 Phase 3
0.7485 Intermediate Similarity NPD7229 Phase 3
0.7483 Intermediate Similarity NPD1203 Approved
0.7483 Intermediate Similarity NPD2797 Approved
0.7455 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD6832 Phase 2
0.745 Intermediate Similarity NPD1610 Phase 2
0.7444 Intermediate Similarity NPD4287 Approved
0.7439 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5124 Phase 1
0.7436 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4361 Phase 2
0.7423 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD3225 Approved
0.7415 Intermediate Similarity NPD1548 Phase 1
0.7414 Intermediate Similarity NPD7177 Discontinued
0.7405 Intermediate Similarity NPD7033 Discontinued
0.7403 Intermediate Similarity NPD4625 Phase 3
0.7391 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD3787 Discontinued
0.7372 Intermediate Similarity NPD943 Approved
0.7337 Intermediate Similarity NPD4288 Approved
0.7333 Intermediate Similarity NPD422 Phase 1
0.7333 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD8151 Discontinued
0.7314 Intermediate Similarity NPD3751 Discontinued
0.7312 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4308 Phase 3
0.7285 Intermediate Similarity NPD9717 Approved
0.7283 Intermediate Similarity NPD5710 Approved
0.7283 Intermediate Similarity NPD5711 Approved
0.7273 Intermediate Similarity NPD6778 Approved
0.7273 Intermediate Similarity NPD6780 Approved
0.7273 Intermediate Similarity NPD6782 Approved
0.7273 Intermediate Similarity NPD6781 Approved
0.7273 Intermediate Similarity NPD6776 Approved
0.7273 Intermediate Similarity NPD6777 Approved
0.7273 Intermediate Similarity NPD6779 Approved
0.7262 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD3267 Approved
0.7255 Intermediate Similarity NPD3266 Approved
0.7244 Intermediate Similarity NPD3764 Approved
0.7235 Intermediate Similarity NPD2296 Approved
0.7225 Intermediate Similarity NPD7199 Phase 2
0.7225 Intermediate Similarity NPD7584 Approved
0.7222 Intermediate Similarity NPD2654 Approved
0.7219 Intermediate Similarity NPD1201 Approved
0.7212 Intermediate Similarity NPD7447 Phase 1
0.7211 Intermediate Similarity NPD7870 Phase 2
0.7211 Intermediate Similarity NPD7871 Phase 2
0.7181 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD3972 Approved
0.7171 Intermediate Similarity NPD1608 Approved
0.7165 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD7783 Phase 2
0.7158 Intermediate Similarity NPD7696 Phase 3
0.7158 Intermediate Similarity NPD7697 Approved
0.7158 Intermediate Similarity NPD7435 Discontinued
0.7158 Intermediate Similarity NPD7698 Approved
0.7152 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7213 Phase 3
0.7152 Intermediate Similarity NPD7212 Phase 2
0.7143 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1164 Approved
0.7143 Intermediate Similarity NPD1470 Approved
0.7135 Intermediate Similarity NPD1729 Discontinued
0.7134 Intermediate Similarity NPD6798 Discontinued
0.7119 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6273 Approved
0.7059 Intermediate Similarity NPD5889 Approved
0.7059 Intermediate Similarity NPD5890 Approved
0.7051 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD8150 Discontinued
0.7044 Intermediate Similarity NPD4307 Phase 2
0.7044 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1613 Approved
0.7025 Intermediate Similarity NPD1296 Phase 2
0.7018 Intermediate Similarity NPD6844 Discontinued
0.7018 Intermediate Similarity NPD7577 Discontinued
0.7018 Intermediate Similarity NPD37 Approved
0.7018 Intermediate Similarity NPD6280 Approved
0.7018 Intermediate Similarity NPD6279 Approved
0.7016 Intermediate Similarity NPD6823 Phase 2
0.7013 Intermediate Similarity NPD4749 Approved
0.7011 Intermediate Similarity NPD6234 Discontinued
0.701 Intermediate Similarity NPD7701 Phase 2
0.7006 Intermediate Similarity NPD2403 Approved
0.7005 Intermediate Similarity NPD6534 Approved
0.7005 Intermediate Similarity NPD6535 Approved
0.7 Intermediate Similarity NPD230 Phase 1
0.7 Intermediate Similarity NPD447 Suspended

  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