Structure

Physi-Chem Properties

Molecular Weight:  867.29
Volume:  833.255
LogP:  2.34
LogD:  1.336
LogS:  -4.163
# Rotatable Bonds:  14
TPSA:  252.75
# H-Bond Aceptor:  19
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.295
Synthetic Accessibility Score:  7.591
Fsp3:  0.558
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:  -5.313
MDCK Permeability:  0.0001363008632324636
Pgp-inhibitor:  1.0
Pgp-substrate:  0.028
Human Intestinal Absorption (HIA):  0.836
20% Bioavailability (F20%):  0.99
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.048
Plasma Protein Binding (PPB):  34.11607360839844%
Volume Distribution (VD):  1.626
Pgp-substrate:  22.79641342163086%

ADMET: Metabolism

CYP1A2-inhibitor:  0.059
CYP1A2-substrate:  0.014
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.007
CYP2D6-inhibitor:  0.934
CYP2D6-substrate:  0.024
CYP3A4-inhibitor:  0.822
CYP3A4-substrate:  0.268

ADMET: Excretion

Clearance (CL):  2.926
Half-life (T1/2):  0.36

ADMET: Toxicity

hERG Blockers:  0.061
Human Hepatotoxicity (H-HT):  0.964
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.041
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.23
Carcinogencity:  0.062
Eye Corrosion:  0.003
Eye Irritation:  0.032
Respiratory Toxicity:  0.041

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

  Natural Product: NPC87152

Natural Product ID:  NPC87152
Common Name*:   KEGLSEMSUHHFTM-CRCCJMMFSA-N
IUPAC Name:   n.a.
Synonyms:   Aquifoliunine E-I
Standard InCHIKey:  KEGLSEMSUHHFTM-CRCCJMMFSA-N
Standard InCHI:  InChI=1S/C43H49NO18/c1-20-21(2)37(50)61-34-32(56-23(4)46)36(59-26(7)49)42(19-54-22(3)45)35(58-25(6)48)31(60-38(51)27-14-11-10-12-15-27)29-33(57-24(5)47)43(42,41(34,9)53)62-40(29,8)18-55-39(52)28-16-13-17-44-30(20)28/h10-17,20-21,29,31-36,53H,18-19H2,1-9H3/t20-,21-,29+,31-,32-,33+,34-,35+,36-,40-,41-,42+,43-/m0/s1
SMILES:  CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@H]3[C@]([C@@]42O[C@@]([C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)c1ccccc1)[C@H]4OC(=O)C)(C)COC(=O)c1c([C@H]([C@@H](C(=O)O3)C)C)nccc1)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2047341
PubChem CID:   70684079
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO18922 Maytenus ilicifolia Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[15043435]
NPO22471 Maytenus cuzcoina Species Celastraceae Eukaryota root bark;leaves Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador n.a. PMID[16038541]
NPO18922 Maytenus ilicifolia Species Celastraceae Eukaryota root bark n.a. n.a. PMID[17555350]
NPO18922 Maytenus ilicifolia Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[22559947]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO11296 Arthrinium arundinis Species Apiosporaceae Eukaryota n.a. n.a. n.a. PMID[25626143]
NPO22471 Maytenus cuzcoina Species Celastraceae Eukaryota root bark Urubamba, Cusco, Peru n.a. PMID[25927586]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO22524 Ranunculus sceleratus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18922 Maytenus ilicifolia Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22524 Ranunculus sceleratus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22409 Cyanostegia microphylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2217 Valeriana wolgensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1118 Elymus repens Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22806 Euphorbia leuconeura Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22409 Cyanostegia microphylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16652 Centipeda cunninghami Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13457 Acacia pachyphloia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19626 Lavandula dentata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21358 Pyrus ussuriensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20702 Discodermia dissoluta Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22593 Graphis rikuzensis Species Aclididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22524 Ranunculus sceleratus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22471 Maytenus cuzcoina Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11296 Arthrinium arundinis Species Apiosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9876 Isocoma pluriflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20567 Montipora mollis Species Acroporidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22006 Maytenus aquifolium Species Celastraceae 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
NPT634 Organism Leishmania amazonensis Leishmania amazonensis IC50 > 100000.0 nM PMID[564048]
NPT1219 Organism Leishmania chagasi Leishmania chagasi IC50 = 1400.0 nM PMID[564048]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 41900.0 nM PMID[564048]
NPT27 Others Unspecified IC50 = 1847000.0 nM PMID[564048]
NPT2 Others Unspecified Ratio IC50 = 44.0 n.a. PMID[564048]

☑ 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 NPC87152 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 NPC475600
1.0 High Similarity NPC475631
1.0 High Similarity NPC476110
0.995 High Similarity NPC471977
0.995 High Similarity NPC471190
0.995 High Similarity NPC475644
0.995 High Similarity NPC470486
0.9853 High Similarity NPC475303
0.9853 High Similarity NPC475596
0.9851 High Similarity NPC473506
0.9851 High Similarity NPC76565
0.9805 High Similarity NPC30456
0.9803 High Similarity NPC328186
0.9803 High Similarity NPC122968
0.9803 High Similarity NPC477787
0.9803 High Similarity NPC228377
0.9802 High Similarity NPC475137
0.9802 High Similarity NPC475498
0.9756 High Similarity NPC473689
0.9756 High Similarity NPC292416
0.971 High Similarity NPC327769
0.9709 High Similarity NPC244839
0.9709 High Similarity NPC320324
0.9709 High Similarity NPC319880
0.9662 High Similarity NPC237702
0.966 High Similarity NPC316841
0.9655 High Similarity NPC57797
0.9655 High Similarity NPC250807
0.9652 High Similarity NPC84815
0.9652 High Similarity NPC301368
0.9615 High Similarity NPC475406
0.961 High Similarity NPC146824
0.9608 High Similarity NPC473850
0.9606 High Similarity NPC477788
0.9569 High Similarity NPC38959
0.9569 High Similarity NPC327904
0.9563 High Similarity NPC475362
0.9552 High Similarity NPC6981
0.9552 High Similarity NPC471016
0.9522 High Similarity NPC170751
0.9512 High Similarity NPC328154
0.951 High Similarity NPC127026
0.951 High Similarity NPC127720
0.9505 High Similarity NPC294579
0.9505 High Similarity NPC144779
0.9502 High Similarity NPC470306
0.9463 High Similarity NPC471980
0.9455 High Similarity NPC475408
0.9455 High Similarity NPC471014
0.9453 High Similarity NPC4421
0.9434 High Similarity NPC253482
0.9429 High Similarity NPC475426
0.9429 High Similarity NPC35208
0.9409 High Similarity NPC62367
0.9363 High Similarity NPC216428
0.9314 High Similarity NPC75600
0.9314 High Similarity NPC158020
0.9314 High Similarity NPC473115
0.9314 High Similarity NPC6576
0.9314 High Similarity NPC212768
0.9314 High Similarity NPC473089
0.931 High Similarity NPC477909
0.931 High Similarity NPC477907
0.931 High Similarity NPC42678
0.9302 High Similarity NPC475648
0.9272 High Similarity NPC477912
0.9234 High Similarity NPC211920
0.9231 High Similarity NPC477902
0.9194 High Similarity NPC96801
0.9194 High Similarity NPC150698
0.9163 High Similarity NPC472553
0.9143 High Similarity NPC475601
0.9143 High Similarity NPC124029
0.9095 High Similarity NPC148860
0.9087 High Similarity NPC477903
0.9082 High Similarity NPC472555
0.9015 High Similarity NPC304179
0.9015 High Similarity NPC472550
0.9015 High Similarity NPC48042
0.8986 High Similarity NPC477908
0.8986 High Similarity NPC206343
0.8981 High Similarity NPC264674
0.8981 High Similarity NPC319128
0.8972 High Similarity NPC469748
0.8952 High Similarity NPC477911
0.8937 High Similarity NPC477910
0.8925 High Similarity NPC477906
0.8889 High Similarity NPC228331
0.8873 High Similarity NPC63041
0.8868 High Similarity NPC477899
0.8868 High Similarity NPC477900
0.8863 High Similarity NPC235364
0.8844 High Similarity NPC326930
0.8844 High Similarity NPC475301
0.8779 High Similarity NPC26881
0.8768 High Similarity NPC477901
0.8722 High Similarity NPC13603
0.8696 High Similarity NPC328928
0.869 High Similarity NPC473833
0.8678 High Similarity NPC85879
0.8678 High Similarity NPC53255
0.8618 High Similarity NPC91125
0.8612 High Similarity NPC476467
0.8534 High Similarity NPC471978
0.8533 High Similarity NPC475533
0.8525 High Similarity NPC14116
0.8525 High Similarity NPC285411
0.8496 Intermediate Similarity NPC475315
0.8496 Intermediate Similarity NPC324619
0.8486 Intermediate Similarity NPC134384
0.8486 Intermediate Similarity NPC311196
0.8436 Intermediate Similarity NPC280473
0.8436 Intermediate Similarity NPC323551
0.8426 Intermediate Similarity NPC471979
0.8416 Intermediate Similarity NPC238278
0.8407 Intermediate Similarity NPC148896
0.8407 Intermediate Similarity NPC476090
0.8407 Intermediate Similarity NPC180668
0.8407 Intermediate Similarity NPC471013
0.8396 Intermediate Similarity NPC51008
0.8396 Intermediate Similarity NPC41724
0.8371 Intermediate Similarity NPC213143
0.8365 Intermediate Similarity NPC289086
0.8312 Intermediate Similarity NPC471015
0.8294 Intermediate Similarity NPC472752
0.8265 Intermediate Similarity NPC233727
0.8261 Intermediate Similarity NPC10904
0.8233 Intermediate Similarity NPC30570
0.8194 Intermediate Similarity NPC162812
0.8178 Intermediate Similarity NPC292517
0.8173 Intermediate Similarity NPC470279
0.814 Intermediate Similarity NPC165837
0.8113 Intermediate Similarity NPC475835
0.8073 Intermediate Similarity NPC187494
0.8065 Intermediate Similarity NPC193361
0.8065 Intermediate Similarity NPC62844
0.8047 Intermediate Similarity NPC40919
0.8047 Intermediate Similarity NPC470189
0.7991 Intermediate Similarity NPC319556
0.7991 Intermediate Similarity NPC470190
0.79 Intermediate Similarity NPC207531
0.7897 Intermediate Similarity NPC309498
0.7807 Intermediate Similarity NPC471004
0.7803 Intermediate Similarity NPC253314
0.7799 Intermediate Similarity NPC103230
0.7725 Intermediate Similarity NPC37473
0.771 Intermediate Similarity NPC32451
0.771 Intermediate Similarity NPC328559
0.7682 Intermediate Similarity NPC111732
0.757 Intermediate Similarity NPC320748
0.757 Intermediate Similarity NPC324245
0.7559 Intermediate Similarity NPC109922
0.7511 Intermediate Similarity NPC314834
0.7511 Intermediate Similarity NPC141385
0.75 Intermediate Similarity NPC79223
0.75 Intermediate Similarity NPC470280
0.7488 Intermediate Similarity NPC317672
0.7468 Intermediate Similarity NPC70155
0.7455 Intermediate Similarity NPC156044
0.7448 Intermediate Similarity NPC107123
0.7445 Intermediate Similarity NPC140311
0.7442 Intermediate Similarity NPC329024
0.743 Intermediate Similarity NPC135950
0.7427 Intermediate Similarity NPC476516
0.7411 Intermediate Similarity NPC317752
0.7397 Intermediate Similarity NPC183537
0.7391 Intermediate Similarity NPC235885
0.7381 Intermediate Similarity NPC282103
0.738 Intermediate Similarity NPC106593
0.7378 Intermediate Similarity NPC274842
0.7376 Intermediate Similarity NPC314297
0.7376 Intermediate Similarity NPC315545
0.7373 Intermediate Similarity NPC103361
0.7366 Intermediate Similarity NPC244856
0.7366 Intermediate Similarity NPC318299
0.7364 Intermediate Similarity NPC25442
0.7364 Intermediate Similarity NPC12944
0.7364 Intermediate Similarity NPC15406
0.7358 Intermediate Similarity NPC44354
0.7356 Intermediate Similarity NPC317010
0.7356 Intermediate Similarity NPC471997
0.7353 Intermediate Similarity NPC210296
0.735 Intermediate Similarity NPC233334
0.7348 Intermediate Similarity NPC473667
0.7339 Intermediate Similarity NPC24019
0.7336 Intermediate Similarity NPC473441
0.7336 Intermediate Similarity NPC131273
0.7333 Intermediate Similarity NPC124313
0.7333 Intermediate Similarity NPC236424
0.7333 Intermediate Similarity NPC306644
0.7333 Intermediate Similarity NPC207851
0.7331 Intermediate Similarity NPC108342
0.733 Intermediate Similarity NPC315638
0.733 Intermediate Similarity NPC314855
0.733 Intermediate Similarity NPC313796
0.733 Intermediate Similarity NPC313345
0.7327 Intermediate Similarity NPC149708
0.7327 Intermediate Similarity NPC59033
0.7325 Intermediate Similarity NPC77878
0.7317 Intermediate Similarity NPC249614

  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 NPC87152 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
0.8533 High Similarity NPD8468 Phase 2
0.791 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD7396 Approved
0.7647 Intermediate Similarity NPD3794 Approved
0.7647 Intermediate Similarity NPD3795 Approved
0.7554 Intermediate Similarity NPD5891 Approved
0.7431 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD3389 Approved
0.7422 Intermediate Similarity NPD3393 Approved
0.7422 Intermediate Similarity NPD3394 Approved
0.7421 Intermediate Similarity NPD2510 Approved
0.7421 Intermediate Similarity NPD2509 Approved
0.7395 Intermediate Similarity NPD1483 Discontinued
0.7373 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD7069 Discontinued
0.7364 Intermediate Similarity NPD6987 Phase 1
0.7364 Intermediate Similarity NPD3947 Discontinued
0.7358 Intermediate Similarity NPD7233 Approved
0.7358 Intermediate Similarity NPD7234 Approved
0.7318 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD3280 Approved
0.7252 Intermediate Similarity NPD7010 Phase 3
0.7248 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD4417 Approved
0.7237 Intermediate Similarity NPD8325 Phase 3
0.7237 Intermediate Similarity NPD8326 Phase 3
0.7237 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD820 Phase 3
0.7191 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD7708 Approved
0.7169 Intermediate Similarity NPD53 Approved
0.7169 Intermediate Similarity NPD7778 Approved
0.7169 Intermediate Similarity NPD7777 Approved
0.7156 Intermediate Similarity NPD6529 Discontinued
0.7156 Intermediate Similarity NPD4506 Discontinued
0.7143 Intermediate Similarity NPD7803 Approved
0.713 Intermediate Similarity NPD7878 Phase 2
0.71 Intermediate Similarity NPD6770 Approved
0.7093 Intermediate Similarity NPD5475 Discontinued
0.7083 Intermediate Similarity NPD8063 Discontinued
0.708 Intermediate Similarity NPD7955 Approved
0.708 Intermediate Similarity NPD7956 Approved
0.7073 Intermediate Similarity NPD6635 Approved
0.7069 Intermediate Similarity NPD8479 Phase 2
0.7066 Intermediate Similarity NPD7417 Discontinued
0.7061 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD4427 Phase 2
0.7025 Intermediate Similarity NPD7886 Phase 2
0.7025 Intermediate Similarity NPD7885 Phase 2
0.7022 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.6986 Remote Similarity NPD485 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4301 Approved
0.6964 Remote Similarity NPD7187 Phase 2
0.6951 Remote Similarity NPD8248 Clinical (unspecified phase)
0.694 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6934 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6934 Remote Similarity NPD6641 Approved
0.6934 Remote Similarity NPD6642 Approved
0.6926 Remote Similarity NPD7707 Approved
0.6923 Remote Similarity NPD7061 Clinical (unspecified phase)
0.692 Remote Similarity NPD8289 Discontinued
0.6912 Remote Similarity NPD4948 Discontinued
0.6909 Remote Similarity NPD4528 Approved
0.6909 Remote Similarity NPD4529 Approved
0.6909 Remote Similarity NPD4526 Approved
0.6905 Remote Similarity NPD8091 Phase 3
0.6904 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5901 Discontinued
0.6901 Remote Similarity NPD3006 Discontinued
0.6895 Remote Similarity NPD2336 Approved
0.6892 Remote Similarity NPD5003 Discontinued
0.6892 Remote Similarity NPD8485 Approved
0.6889 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6883 Remote Similarity NPD7571 Clinical (unspecified phase)
0.688 Remote Similarity NPD7404 Approved
0.6875 Remote Similarity NPD6962 Phase 2
0.6875 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4862 Clinical (unspecified phase)
0.687 Remote Similarity NPD7470 Discontinued
0.6866 Remote Similarity NPD9271 Approved
0.6864 Remote Similarity NPD8356 Approved
0.6864 Remote Similarity NPD4376 Phase 3
0.6857 Remote Similarity NPD6790 Phase 1
0.6853 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6849 Remote Similarity NPD6281 Approved
0.684 Remote Similarity NPD5866 Approved
0.6838 Remote Similarity NPD7395 Discontinued
0.6833 Remote Similarity NPD5022 Discontinued
0.6829 Remote Similarity NPD6716 Phase 1
0.6826 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6826 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5398 Clinical (unspecified phase)
0.682 Remote Similarity NPD7268 Clinical (unspecified phase)
0.682 Remote Similarity NPD4889 Approved
0.6818 Remote Similarity NPD4373 Phase 2
0.6805 Remote Similarity NPD7688 Phase 1
0.68 Remote Similarity NPD5482 Discontinued
0.68 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7001 Phase 3
0.6798 Remote Similarity NPD7957 Phase 1
0.6798 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6795 Remote Similarity NPD4989 Phase 2
0.6793 Remote Similarity NPD6995 Phase 1
0.6787 Remote Similarity NPD3921 Approved
0.6787 Remote Similarity NPD3924 Approved
0.6787 Remote Similarity NPD3922 Approved
0.6787 Remote Similarity NPD3923 Approved
0.6778 Remote Similarity NPD5640 Discontinued
0.6773 Remote Similarity NPD8435 Approved
0.6773 Remote Similarity NPD8360 Approved
0.6773 Remote Similarity NPD8361 Approved
0.6771 Remote Similarity NPD2307 Discontinued
0.6768 Remote Similarity NPD8466 Approved
0.6768 Remote Similarity NPD8465 Approved
0.6768 Remote Similarity NPD8467 Approved
0.6758 Remote Similarity NPD6791 Phase 2
0.6756 Remote Similarity NPD6999 Discontinued
0.6756 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6754 Remote Similarity NPD2831 Approved
0.675 Remote Similarity NPD8430 Approved
0.6748 Remote Similarity NPD6026 Approved
0.6746 Remote Similarity NPD5088 Discontinued
0.6739 Remote Similarity NPD7191 Phase 2
0.6736 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6736 Remote Similarity NPD3925 Approved
0.6735 Remote Similarity NPD5805 Approved
0.6733 Remote Similarity NPD8101 Phase 3
0.6731 Remote Similarity NPD8364 Approved
0.6731 Remote Similarity NPD8363 Approved
0.6726 Remote Similarity NPD4601 Approved
0.6726 Remote Similarity NPD6479 Discontinued
0.6726 Remote Similarity NPD4600 Approved
0.6723 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7576 Discontinued
0.672 Remote Similarity NPD6276 Discontinued
0.6715 Remote Similarity NPD2582 Approved
0.6715 Remote Similarity NPD2581 Approved
0.6711 Remote Similarity NPD6176 Phase 1
0.6708 Remote Similarity NPD7426 Phase 1
0.6707 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6698 Remote Similarity NPD1573 Approved
0.6698 Remote Similarity NPD1575 Approved
0.6697 Remote Similarity NPD2565 Phase 2
0.6697 Remote Similarity NPD2564 Approved
0.6696 Remote Similarity NPD5429 Discontinued
0.6696 Remote Similarity NPD7562 Approved
0.6695 Remote Similarity NPD3815 Phase 1
0.6695 Remote Similarity NPD3816 Phase 1
0.6695 Remote Similarity NPD3354 Phase 2
0.6694 Remote Similarity NPD4952 Phase 3
0.6694 Remote Similarity NPD8412 Phase 1
0.6683 Remote Similarity NPD9075 Approved
0.6683 Remote Similarity NPD9074 Approved
0.6682 Remote Similarity NPD3178 Discontinued
0.6682 Remote Similarity NPD6361 Phase 2
0.6682 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6681 Remote Similarity NPD8160 Phase 2
0.668 Remote Similarity NPD6494 Phase 2
0.668 Remote Similarity NPD6292 Clinical (unspecified phase)
0.668 Remote Similarity NPD6553 Clinical (unspecified phase)
0.668 Remote Similarity NPD5488 Discontinued
0.6679 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8426 Approved
0.6667 Remote Similarity NPD1631 Approved
0.6667 Remote Similarity NPD7424 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8460 Approved
0.6667 Remote Similarity NPD8459 Approved
0.6667 Remote Similarity NPD8425 Approved
0.6654 Remote Similarity NPD6228 Discontinued
0.6654 Remote Similarity NPD8463 Approved
0.6652 Remote Similarity NPD5416 Discontinued
0.6652 Remote Similarity NPD7944 Discontinued
0.6652 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6642 Remote Similarity NPD8428 Approved
0.6642 Remote Similarity NPD8429 Approved
0.6642 Remote Similarity NPD8427 Approved
0.6641 Remote Similarity NPD7169 Suspended
0.6639 Remote Similarity NPD6242 Discontinued
0.6639 Remote Similarity NPD1996 Discontinued
0.6638 Remote Similarity NPD4897 Phase 2
0.6638 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6627 Remote Similarity NPD8102 Discontinued
0.6624 Remote Similarity NPD4429 Discontinued
0.6622 Remote Similarity NPD7818 Clinical (unspecified phase)
0.662 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6614 Remote Similarity NPD8100 Phase 3
0.6613 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6612 Remote Similarity NPD4086 Phase 1
0.6612 Remote Similarity NPD3259 Approved
0.6612 Remote Similarity NPD7558 Phase 2
0.6611 Remote Similarity NPD5147 Discontinued
0.6611 Remote Similarity NPD5507 Approved
0.6611 Remote Similarity NPD6298 Discontinued

  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