Structure

Physi-Chem Properties

Molecular Weight:  472.1
Volume:  442.466
LogP:  2.28
LogD:  1.053
LogS:  -3.951
# Rotatable Bonds:  5
TPSA:  186.37
# H-Bond Aceptor:  11
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.218
Synthetic Accessibility Score:  3.685
Fsp3:  0.174
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.574
MDCK Permeability:  5.617112947220448e-06
Pgp-inhibitor:  0.035
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.55
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  89.82464599609375%
Volume Distribution (VD):  0.523
Pgp-substrate:  9.706511497497559%

ADMET: Metabolism

CYP1A2-inhibitor:  0.229
CYP1A2-substrate:  0.164
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.611
CYP2C9-substrate:  0.321
CYP2D6-inhibitor:  0.027
CYP2D6-substrate:  0.198
CYP3A4-inhibitor:  0.124
CYP3A4-substrate:  0.128

ADMET: Excretion

Clearance (CL):  12.973
Half-life (T1/2):  0.932

ADMET: Toxicity

hERG Blockers:  0.159
Human Hepatotoxicity (H-HT):  0.166
Drug-inuced Liver Injury (DILI):  0.924
AMES Toxicity:  0.174
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.522
Skin Sensitization:  0.962
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.926
Respiratory Toxicity:  0.027

Download Data

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

  Natural Product: NPC87317

Natural Product ID:  NPC87317
Common Name*:   (-)-Epigallocatechin-3-(3''-O-Methyl)Gallate
IUPAC Name:   [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4-dihydroxy-5-methoxybenzoate
Synonyms:  
Standard InCHIKey:  WVRDOLPMKOCJRJ-DENIHFKCSA-N
Standard InCHI:  InChI=1S/C23H20O11/c1-32-18-5-10(4-16(28)21(18)30)23(31)34-19-8-12-13(25)6-11(24)7-17(12)33-22(19)9-2-14(26)20(29)15(27)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1
SMILES:  COc1cc(cc(c1O)O)C(=O)O[C@@H]1Cc2c(O)cc(cc2O[C@@H]1c1cc(O)c(c(c1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL562716
PubChem CID:   9804842
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0003012] Flavan-3-ols
            • [CHEMONTID:0001584] Catechins
              • [CHEMONTID:0001587] Catechin gallates

*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
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.foodchem.2013.08.121]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Flowers n.a. n.a. PMID[16180814]
NPO8258 Camellia sinensis Species Theaceae Eukaryota seeds Shizuoka prefecture, Japan n.a. PMID[16499314]
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. PMID[17887722]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[21434603]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota roots n.a. n.a. PMID[21911291]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. flower n.a. PMID[21922925]
NPO8258 Camellia sinensis Species Theaceae Eukaryota flower buds n.a. n.a. PMID[21925888]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[22312717]
NPO8258 Camellia sinensis Species Theaceae Eukaryota leaves n.a. n.a. PMID[22377672]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. leaf n.a. PMID[23265489]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaves Bandung, West Java, Indonesia PMID[23621359]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26848504]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[28802670]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[31675225]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae Eukaryota n.a. n.a. n.a. PMID[8450325]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8609085]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11657 Angelica lucida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1697 Bitis gabonica Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3995 Limonium sinense Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13472 Cotula cinerea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11934 Castanea vesca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9252 Adina sessilifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5735 Solidago serotina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14564 Oophaga pumilio Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6845 Mimusops caffra Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11823 Marine actinobacterium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21255 Hymenoxys insignis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae 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
NPO8258 NPC87317 Tea Or Coffee Leaf 19.7 19.7 19.7 mg/100g Database [DUKE]

☑ 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
NPT4015 Individual Protein Matrix metalloproteinase 14 Homo sapiens IC50 = 1700.0 nM PMID[448641]
NPT4016 Individual Protein Matrix metalloproteinase 7 Homo sapiens IC50 = 20000.0 nM PMID[448641]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 8700.0 nM PMID[448641]

☑ 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 NPC87317 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
0.9934 High Similarity NPC53889
0.9867 High Similarity NPC250436
0.9867 High Similarity NPC104983
0.9867 High Similarity NPC88803
0.9867 High Similarity NPC300845
0.9867 High Similarity NPC291948
0.9801 High Similarity NPC38779
0.9801 High Similarity NPC289322
0.9801 High Similarity NPC114179
0.9801 High Similarity NPC160512
0.9801 High Similarity NPC68324
0.9801 High Similarity NPC156818
0.9735 High Similarity NPC318432
0.9673 High Similarity NPC24164
0.9551 High Similarity NPC142614
0.9536 High Similarity NPC474656
0.943 High Similarity NPC473818
0.9423 High Similarity NPC476372
0.9423 High Similarity NPC476371
0.9419 High Similarity NPC24627
0.9342 High Similarity NPC75695
0.9313 High Similarity NPC476365
0.9304 High Similarity NPC471788
0.9299 High Similarity NPC33298
0.9299 High Similarity NPC285108
0.9295 High Similarity NPC476373
0.9286 High Similarity NPC222185
0.9245 High Similarity NPC207575
0.9245 High Similarity NPC13481
0.9236 High Similarity NPC158188
0.9231 High Similarity NPC37502
0.9231 High Similarity NPC267627
0.9231 High Similarity NPC40702
0.9211 High Similarity NPC473091
0.9202 High Similarity NPC79736
0.9202 High Similarity NPC67629
0.9198 High Similarity NPC88560
0.9198 High Similarity NPC175230
0.9198 High Similarity NPC172033
0.9193 High Similarity NPC149011
0.9193 High Similarity NPC180768
0.9193 High Similarity NPC204937
0.9187 High Similarity NPC243877
0.9187 High Similarity NPC14662
0.9177 High Similarity NPC476247
0.9172 High Similarity NPC101731
0.9172 High Similarity NPC289346
0.9172 High Similarity NPC203020
0.9172 High Similarity NPC239966
0.9167 High Similarity NPC1913
0.9167 High Similarity NPC247713
0.9146 High Similarity NPC267549
0.9145 High Similarity NPC476394
0.9145 High Similarity NPC107636
0.9145 High Similarity NPC98809
0.9136 High Similarity NPC271848
0.9136 High Similarity NPC212038
0.9136 High Similarity NPC262580
0.9136 High Similarity NPC476370
0.9136 High Similarity NPC289396
0.9136 High Similarity NPC65333
0.9136 High Similarity NPC100251
0.9136 High Similarity NPC81332
0.9119 High Similarity NPC121290
0.9114 High Similarity NPC305987
0.9114 High Similarity NPC84324
0.9114 High Similarity NPC142252
0.9114 High Similarity NPC165970
0.9114 High Similarity NPC134783
0.9114 High Similarity NPC112418
0.9114 High Similarity NPC113163
0.9114 High Similarity NPC66618
0.9114 High Similarity NPC288131
0.9108 High Similarity NPC284127
0.9108 High Similarity NPC160780
0.9108 High Similarity NPC289811
0.9108 High Similarity NPC476410
0.9108 High Similarity NPC172202
0.9103 High Similarity NPC165483
0.9097 High Similarity NPC43872
0.9097 High Similarity NPC18727
0.9097 High Similarity NPC116850
0.9097 High Similarity NPC238672
0.9097 High Similarity NPC144801
0.9097 High Similarity NPC469888
0.9097 High Similarity NPC291510
0.9097 High Similarity NPC197188
0.9085 High Similarity NPC297574
0.908 High Similarity NPC472993
0.908 High Similarity NPC476374
0.908 High Similarity NPC98583
0.9079 High Similarity NPC142528
0.9079 High Similarity NPC472969
0.9073 High Similarity NPC268515
0.9073 High Similarity NPC40222
0.9068 High Similarity NPC116745
0.9062 High Similarity NPC125039
0.9062 High Similarity NPC7154
0.9062 High Similarity NPC36
0.9062 High Similarity NPC72787
0.9062 High Similarity NPC58223
0.9062 High Similarity NPC36916
0.9062 High Similarity NPC477840
0.9062 High Similarity NPC7688
0.9057 High Similarity NPC219927
0.9057 High Similarity NPC90905
0.9057 High Similarity NPC471745
0.9057 High Similarity NPC4013
0.9057 High Similarity NPC477841
0.9051 High Similarity NPC119125
0.9051 High Similarity NPC471744
0.9051 High Similarity NPC166277
0.9045 High Similarity NPC475267
0.9045 High Similarity NPC299520
0.9045 High Similarity NPC183851
0.9045 High Similarity NPC129684
0.9045 High Similarity NPC48208
0.9045 High Similarity NPC156057
0.9045 High Similarity NPC474836
0.9045 High Similarity NPC291508
0.9045 High Similarity NPC472860
0.9045 High Similarity NPC35598
0.9045 High Similarity NPC133984
0.9045 High Similarity NPC474208
0.9045 High Similarity NPC162869
0.9045 High Similarity NPC210084
0.9045 High Similarity NPC222689
0.9045 High Similarity NPC63454
0.9045 High Similarity NPC108456
0.9045 High Similarity NPC99597
0.9038 High Similarity NPC470327
0.9038 High Similarity NPC45849
0.9038 High Similarity NPC477503
0.9038 High Similarity NPC145425
0.9038 High Similarity NPC200761
0.9036 High Similarity NPC117668
0.9032 High Similarity NPC236637
0.9032 High Similarity NPC257648
0.9032 High Similarity NPC219582
0.9032 High Similarity NPC289968
0.9032 High Similarity NPC302950
0.9032 High Similarity NPC477231
0.903 High Similarity NPC476618
0.903 High Similarity NPC472387
0.903 High Similarity NPC476622
0.903 High Similarity NPC476623
0.903 High Similarity NPC476620
0.903 High Similarity NPC476619
0.903 High Similarity NPC476621
0.9026 High Similarity NPC243891
0.9026 High Similarity NPC338131
0.9018 High Similarity NPC67134
0.9018 High Similarity NPC47140
0.9012 High Similarity NPC280493
0.9012 High Similarity NPC229687
0.9012 High Similarity NPC197708
0.9012 High Similarity NPC658
0.9012 High Similarity NPC476279
0.9006 High Similarity NPC43065
0.9 High Similarity NPC45943
0.9 High Similarity NPC67959
0.8994 High Similarity NPC471211
0.8994 High Similarity NPC469889
0.8994 High Similarity NPC109061
0.8994 High Similarity NPC311803
0.8994 High Similarity NPC25389
0.8994 High Similarity NPC26326
0.8994 High Similarity NPC472859
0.8994 High Similarity NPC471212
0.8981 High Similarity NPC235165
0.8981 High Similarity NPC209614
0.8981 High Similarity NPC195796
0.8981 High Similarity NPC470328
0.8981 High Similarity NPC35038
0.8981 High Similarity NPC227062
0.8981 High Similarity NPC54928
0.8981 High Similarity NPC472916
0.8981 High Similarity NPC250922
0.8981 High Similarity NPC255106
0.8981 High Similarity NPC278778
0.8981 High Similarity NPC472626
0.8981 High Similarity NPC291878
0.8976 High Similarity NPC80956
0.8974 High Similarity NPC178134
0.897 High Similarity NPC472991
0.897 High Similarity NPC472992
0.897 High Similarity NPC472723
0.8968 High Similarity NPC228662
0.8968 High Similarity NPC476434
0.8968 High Similarity NPC267091
0.8968 High Similarity NPC31363
0.8963 High Similarity NPC46640
0.8963 High Similarity NPC263119
0.8963 High Similarity NPC34436
0.8963 High Similarity NPC166674
0.8963 High Similarity NPC473550
0.8963 High Similarity NPC219600
0.8957 High Similarity NPC224462
0.8951 High Similarity NPC45400
0.8951 High Similarity NPC295082

  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 NPC87317 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
0.9867 High Similarity NPD4868 Clinical (unspecified phase)
0.9136 High Similarity NPD7993 Clinical (unspecified phase)
0.9062 High Similarity NPD6166 Phase 2
0.9062 High Similarity NPD6167 Clinical (unspecified phase)
0.9062 High Similarity NPD6168 Clinical (unspecified phase)
0.9032 High Similarity NPD1934 Approved
0.8974 High Similarity NPD1465 Phase 2
0.8896 High Similarity NPD5844 Phase 1
0.8854 High Similarity NPD2393 Clinical (unspecified phase)
0.8734 High Similarity NPD2801 Approved
0.8727 High Similarity NPD7074 Phase 3
0.872 High Similarity NPD3818 Discontinued
0.8683 High Similarity NPD4338 Clinical (unspecified phase)
0.8679 High Similarity NPD3817 Phase 2
0.8667 High Similarity NPD7054 Approved
0.8625 High Similarity NPD3882 Suspended
0.8614 High Similarity NPD7472 Approved
0.8589 High Similarity NPD6232 Discontinued
0.8571 High Similarity NPD7075 Discontinued
0.8491 Intermediate Similarity NPD7411 Suspended
0.8457 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6797 Phase 2
0.8434 Intermediate Similarity NPD7473 Discontinued
0.8428 Intermediate Similarity NPD4380 Phase 2
0.8402 Intermediate Similarity NPD7251 Discontinued
0.84 Intermediate Similarity NPD230 Phase 1
0.8397 Intermediate Similarity NPD1511 Approved
0.8385 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD5494 Approved
0.8353 Intermediate Similarity NPD7808 Phase 3
0.8293 Intermediate Similarity NPD6234 Discontinued
0.8291 Intermediate Similarity NPD1512 Approved
0.8272 Intermediate Similarity NPD7819 Suspended
0.8221 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8221 Intermediate Similarity NPD5402 Approved
0.821 Intermediate Similarity NPD6801 Discontinued
0.8194 Intermediate Similarity NPD1549 Phase 2
0.8193 Intermediate Similarity NPD7199 Phase 2
0.8193 Intermediate Similarity NPD6959 Discontinued
0.8166 Intermediate Similarity NPD7228 Approved
0.8165 Intermediate Similarity NPD6799 Approved
0.8155 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD6190 Approved
0.8141 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD37 Approved
0.8095 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD1613 Approved
0.8089 Intermediate Similarity NPD4628 Phase 3
0.8089 Intermediate Similarity NPD3750 Approved
0.8081 Intermediate Similarity NPD6559 Discontinued
0.8075 Intermediate Similarity NPD1653 Approved
0.8061 Intermediate Similarity NPD7768 Phase 2
0.8061 Intermediate Similarity NPD4967 Phase 2
0.8061 Intermediate Similarity NPD4965 Approved
0.8061 Intermediate Similarity NPD4966 Approved
0.805 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD5403 Approved
0.8012 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD3749 Approved
0.8 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD7685 Pre-registration
0.7975 Intermediate Similarity NPD6599 Discontinued
0.7966 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD2796 Approved
0.7947 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD3027 Phase 3
0.7888 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD5401 Approved
0.7885 Intermediate Similarity NPD1510 Phase 2
0.7848 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD447 Suspended
0.7784 Intermediate Similarity NPD5353 Approved
0.7778 Intermediate Similarity NPD2533 Approved
0.7778 Intermediate Similarity NPD3926 Phase 2
0.7778 Intermediate Similarity NPD2534 Approved
0.7778 Intermediate Similarity NPD2532 Approved
0.7771 Intermediate Similarity NPD3748 Approved
0.7751 Intermediate Similarity NPD919 Approved
0.775 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD1240 Approved
0.7742 Intermediate Similarity NPD943 Approved
0.7727 Intermediate Similarity NPD6798 Discontinued
0.7722 Intermediate Similarity NPD2935 Discontinued
0.7722 Intermediate Similarity NPD1551 Phase 2
0.7712 Intermediate Similarity NPD4908 Phase 1
0.7697 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD8313 Approved
0.7684 Intermediate Similarity NPD8312 Approved
0.768 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD5242 Approved
0.7673 Intermediate Similarity NPD7266 Discontinued
0.767 Intermediate Similarity NPD7240 Approved
0.7667 Intermediate Similarity NPD9269 Phase 2
0.7647 Intermediate Similarity NPD9494 Approved
0.7644 Intermediate Similarity NPD3751 Discontinued
0.7643 Intermediate Similarity NPD1607 Approved
0.7619 Intermediate Similarity NPD8455 Phase 2
0.7613 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD3226 Approved
0.758 Intermediate Similarity NPD1933 Approved
0.7564 Intermediate Similarity NPD6233 Phase 2
0.7558 Intermediate Similarity NPD1247 Approved
0.7558 Intermediate Similarity NPD8127 Discontinued
0.7539 Intermediate Similarity NPD8151 Discontinued
0.7528 Intermediate Similarity NPD7549 Discontinued
0.7514 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5953 Discontinued
0.7514 Intermediate Similarity NPD7229 Phase 3
0.7514 Intermediate Similarity NPD3787 Discontinued
0.75 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6100 Approved
0.75 Intermediate Similarity NPD6385 Approved
0.75 Intermediate Similarity NPD6386 Approved
0.75 Intermediate Similarity NPD6099 Approved
0.7472 Intermediate Similarity NPD7039 Approved
0.7472 Intermediate Similarity NPD7038 Approved
0.747 Intermediate Similarity NPD920 Approved
0.7423 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD7286 Phase 2
0.74 Intermediate Similarity NPD9268 Approved
0.7394 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD3764 Approved
0.7386 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7458 Discontinued
0.7372 Intermediate Similarity NPD6832 Phase 2
0.7363 Intermediate Similarity NPD8150 Discontinued
0.7363 Intermediate Similarity NPD8434 Phase 2
0.7362 Intermediate Similarity NPD1652 Phase 2
0.7362 Intermediate Similarity NPD1243 Approved
0.7362 Intermediate Similarity NPD2800 Approved
0.7358 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD5124 Phase 1
0.7358 Intermediate Similarity NPD6355 Discontinued
0.7349 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2346 Discontinued
0.734 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4308 Phase 3
0.7329 Intermediate Similarity NPD2799 Discontinued
0.7329 Intermediate Similarity NPD7033 Discontinued
0.732 Intermediate Similarity NPD1608 Approved
0.7314 Intermediate Similarity NPD5711 Approved
0.7314 Intermediate Similarity NPD5710 Approved
0.7305 Intermediate Similarity NPD6273 Approved
0.729 Intermediate Similarity NPD1203 Approved
0.729 Intermediate Similarity NPD2797 Approved
0.7289 Intermediate Similarity NPD7390 Discontinued
0.7283 Intermediate Similarity NPD6971 Discontinued
0.7282 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD7783 Phase 2
0.7278 Intermediate Similarity NPD3268 Approved
0.7278 Intermediate Similarity NPD2313 Discontinued
0.7277 Intermediate Similarity NPD7680 Approved
0.7277 Intermediate Similarity NPD7435 Discontinued
0.7267 Intermediate Similarity NPD7097 Phase 1
0.7267 Intermediate Similarity NPD4288 Approved
0.7255 Intermediate Similarity NPD1610 Phase 2
0.7255 Intermediate Similarity NPD422 Phase 1
0.7253 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD7177 Discontinued
0.7239 Intermediate Similarity NPD2344 Approved
0.7229 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3225 Approved
0.7222 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD9545 Approved
0.7216 Intermediate Similarity NPD7585 Approved
0.7212 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7003 Approved
0.7212 Intermediate Similarity NPD4110 Phase 3
0.7212 Intermediate Similarity NPD8166 Discontinued
0.7211 Intermediate Similarity NPD6777 Approved
0.7211 Intermediate Similarity NPD6780 Approved
0.7211 Intermediate Similarity NPD6776 Approved
0.7211 Intermediate Similarity NPD6779 Approved
0.7211 Intermediate Similarity NPD6781 Approved
0.7211 Intermediate Similarity NPD6778 Approved
0.7211 Intermediate Similarity NPD6782 Approved
0.7188 Intermediate Similarity NPD4060 Phase 1
0.7176 Intermediate Similarity NPD3455 Phase 2
0.7165 Intermediate Similarity NPD7583 Approved
0.7152 Intermediate Similarity NPD6674 Discontinued
0.7134 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7440 Discontinued
0.7124 Intermediate Similarity NPD17 Approved
0.7107 Intermediate Similarity NPD7095 Approved
0.7105 Intermediate Similarity NPD1548 Phase 1
0.7099 Intermediate Similarity NPD6651 Approved
0.7097 Intermediate Similarity NPD9717 Approved
0.7097 Intermediate Similarity NPD4287 Approved
0.7089 Intermediate Similarity NPD3018 Phase 2

  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