Structure

Physi-Chem Properties

Molecular Weight:  820.31
Volume:  812.426
LogP:  2.242
LogD:  1.105
LogS:  -3.749
# Rotatable Bonds:  16
TPSA:  226.95
# H-Bond Aceptor:  17
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.196
Synthetic Accessibility Score:  6.036
Fsp3:  0.476
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:  -5.353
MDCK Permeability:  0.00012253083696123213
Pgp-inhibitor:  1.0
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.909
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.125
Plasma Protein Binding (PPB):  65.69682312011719%
Volume Distribution (VD):  1.698
Pgp-substrate:  23.312894821166992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.028
CYP2C19-inhibitor:  0.153
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.398
CYP2C9-substrate:  0.027
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.018
CYP3A4-inhibitor:  0.901
CYP3A4-substrate:  0.338

ADMET: Excretion

Clearance (CL):  2.967
Half-life (T1/2):  0.895

ADMET: Toxicity

hERG Blockers:  0.109
Human Hepatotoxicity (H-HT):  0.992
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.289
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.248
Carcinogencity:  0.039
Eye Corrosion:  0.004
Eye Irritation:  0.209
Respiratory Toxicity:  0.02

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

  Natural Product: NPC207531

Natural Product ID:  NPC207531
Common Name*:   Euphosalicin
IUPAC Name:   [(1S,2R,4R,6R,7R,9E,11R,13R,15R,16R)-2,4,7,13,16-pentaacetyloxy-7,11,15-trimethyl-3-methylidene-12-oxo-15-(pyridine-3-carbonyloxy)-6-bicyclo[11.3.0]hexadec-9-enyl] pyridine-3-carboxylate
Synonyms:   Euphosalicin
Standard InCHIKey:  VCNSIDRPGQLVOC-XQFXQYKMSA-N
Standard InCHI:  InChI=1S/C42H48N2O15/c1-23-13-10-16-40(8,57-28(6)48)33(56-38(51)30-14-11-17-43-20-30)19-32(53-25(3)45)24(2)35(54-26(4)46)34-37(55-27(5)47)41(9,22-42(34,36(23)50)58-29(7)49)59-39(52)31-15-12-18-44-21-31/h10-15,17-18,20-21,23,32-35,37H,2,16,19,22H2,1,3-9H3/b13-10+/t23-,32-,33-,34+,35+,37-,40-,41-,42-/m1/s1
SMILES:  CC(=O)O[C@@H]1C[C@@H](OC(=O)c2cccnc2)[C@@](C)(C/C=C/[C@H](C(=O)[C@@]2([C@@H]([C@H](C1=C)OC(=O)C)[C@@H](OC(=O)C)[C@](C2)(C)OC(=O)c1cccnc1)OC(=O)C)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1812481
PubChem CID:   10259855
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0001322] Pyridinecarboxylic acids and derivatives
          • [CHEMONTID:0002414] Pyridinecarboxylic acids

*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
NPO20289 Dracocephalum tanguticum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19499937]
NPO20289 Dracocephalum tanguticum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20932762]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[21612217]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21612217]
NPO10441 Euphorbia salicifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[21612217]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[27447736]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[32233482]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17973 Sinapis arvensis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17973 Sinapis arvensis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22664 Uapaca paludosa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18416 Streptomyces fulvoviolaceus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17916 Monoon viride Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20289 Dracocephalum tanguticum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20895 Lotus suaveolens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17973 Sinapis arvensis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23112 Rubia tinctoria Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22613 Helichrysum sutherlandi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10441 Euphorbia salicifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20783 Fissistigma bracteolatum Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9653 Corynebacterium pseudotuberculosis Species Corynebacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21966 Funiculina quadrangularis Species Funiculinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20156 Bolbitis subcordata Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22849 Glaucidium palmatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22534 Lonicera tatarica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21842 Musanga cecropioides Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3099 Euphorbia esula Species Euphorbiaceae 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
NPT165 Cell Line HeLa Homo sapiens GI = 14.5 % PMID[528923]
NPT2738 Cell Line Ishikawa Homo sapiens GI = 0.9 % PMID[528923]
NPT83 Cell Line MCF7 Homo sapiens GI = 6.3 % PMID[528923]
NPT165 Cell Line HeLa Homo sapiens GI = 18.1 % PMID[528923]
NPT2738 Cell Line Ishikawa Homo sapiens GI = 7.6 % PMID[528923]
NPT83 Cell Line MCF7 Homo sapiens GI = 20.0 % PMID[528923]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 1.9 n.a. PMID[528923]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 12.3 n.a. PMID[528923]

☑ 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 NPC207531 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
0.9896 High Similarity NPC319556
0.9585 High Similarity NPC40919
0.9585 High Similarity NPC470189
0.943 High Similarity NPC470190
0.9394 High Similarity NPC187494
0.9118 High Similarity NPC233727
0.91 High Similarity NPC193361
0.91 High Similarity NPC62844
0.9095 High Similarity NPC165837
0.9045 High Similarity NPC476467
0.9 High Similarity NPC51008
0.9 High Similarity NPC41724
0.895 High Similarity NPC323551
0.895 High Similarity NPC280473
0.8857 High Similarity NPC213143
0.8804 High Similarity NPC311196
0.8804 High Similarity NPC134384
0.8756 High Similarity NPC14116
0.8756 High Similarity NPC285411
0.8726 High Similarity NPC238278
0.8706 High Similarity NPC472752
0.8571 High Similarity NPC26881
0.8476 Intermediate Similarity NPC235364
0.8469 Intermediate Similarity NPC477901
0.8411 Intermediate Similarity NPC91125
0.8404 Intermediate Similarity NPC475601
0.8396 Intermediate Similarity NPC477899
0.8396 Intermediate Similarity NPC477900
0.8389 Intermediate Similarity NPC477911
0.8372 Intermediate Similarity NPC96801
0.8372 Intermediate Similarity NPC477906
0.8372 Intermediate Similarity NPC150698
0.8333 Intermediate Similarity NPC472555
0.8317 Intermediate Similarity NPC264674
0.8317 Intermediate Similarity NPC4421
0.831 Intermediate Similarity NPC328154
0.8255 Intermediate Similarity NPC477912
0.8255 Intermediate Similarity NPC477903
0.8238 Intermediate Similarity NPC477908
0.8238 Intermediate Similarity NPC206343
0.8233 Intermediate Similarity NPC211920
0.8233 Intermediate Similarity NPC124029
0.823 Intermediate Similarity NPC319128
0.823 Intermediate Similarity NPC228331
0.8199 Intermediate Similarity NPC62367
0.8199 Intermediate Similarity NPC158020
0.8199 Intermediate Similarity NPC6576
0.8199 Intermediate Similarity NPC75600
0.8199 Intermediate Similarity NPC473089
0.8199 Intermediate Similarity NPC473115
0.8199 Intermediate Similarity NPC212768
0.8186 Intermediate Similarity NPC148860
0.8174 Intermediate Similarity NPC35208
0.8165 Intermediate Similarity NPC469748
0.816 Intermediate Similarity NPC216428
0.816 Intermediate Similarity NPC301368
0.816 Intermediate Similarity NPC84815
0.8152 Intermediate Similarity NPC471016
0.8146 Intermediate Similarity NPC289086
0.814 Intermediate Similarity NPC477902
0.8134 Intermediate Similarity NPC472553
0.8108 Intermediate Similarity NPC253482
0.8104 Intermediate Similarity NPC477907
0.8104 Intermediate Similarity NPC477910
0.8104 Intermediate Similarity NPC470306
0.8104 Intermediate Similarity NPC477909
0.8104 Intermediate Similarity NPC42678
0.8066 Intermediate Similarity NPC471014
0.8066 Intermediate Similarity NPC6981
0.8066 Intermediate Similarity NPC475408
0.8047 Intermediate Similarity NPC477788
0.8047 Intermediate Similarity NPC127026
0.8047 Intermediate Similarity NPC127720
0.8028 Intermediate Similarity NPC144779
0.8028 Intermediate Similarity NPC294579
0.8009 Intermediate Similarity NPC471980
0.8009 Intermediate Similarity NPC327769
0.8 Intermediate Similarity NPC244839
0.8 Intermediate Similarity NPC320324
0.8 Intermediate Similarity NPC319880
0.8 Intermediate Similarity NPC475648
0.799 Intermediate Similarity NPC48042
0.799 Intermediate Similarity NPC472550
0.799 Intermediate Similarity NPC304179
0.7982 Intermediate Similarity NPC146824
0.7964 Intermediate Similarity NPC237702
0.7955 Intermediate Similarity NPC292416
0.7955 Intermediate Similarity NPC473689
0.7945 Intermediate Similarity NPC475362
0.7936 Intermediate Similarity NPC473506
0.7926 Intermediate Similarity NPC250807
0.7926 Intermediate Similarity NPC76565
0.7926 Intermediate Similarity NPC57797
0.79 Intermediate Similarity NPC475600
0.79 Intermediate Similarity NPC228377
0.79 Intermediate Similarity NPC476110
0.79 Intermediate Similarity NPC475631
0.79 Intermediate Similarity NPC87152
0.79 Intermediate Similarity NPC328186
0.79 Intermediate Similarity NPC122968
0.79 Intermediate Similarity NPC477787
0.7892 Intermediate Similarity NPC327904
0.7892 Intermediate Similarity NPC38959
0.789 Intermediate Similarity NPC475498
0.789 Intermediate Similarity NPC473850
0.789 Intermediate Similarity NPC475137
0.7864 Intermediate Similarity NPC475644
0.7864 Intermediate Similarity NPC471190
0.7864 Intermediate Similarity NPC471977
0.7864 Intermediate Similarity NPC470486
0.7857 Intermediate Similarity NPC63041
0.7848 Intermediate Similarity NPC475426
0.7848 Intermediate Similarity NPC475406
0.7847 Intermediate Similarity NPC309498
0.7817 Intermediate Similarity NPC475315
0.7817 Intermediate Similarity NPC324619
0.7793 Intermediate Similarity NPC316841
0.7793 Intermediate Similarity NPC475596
0.7793 Intermediate Similarity NPC475303
0.7773 Intermediate Similarity NPC475533
0.7758 Intermediate Similarity NPC30456
0.771 Intermediate Similarity NPC292517
0.7692 Intermediate Similarity NPC470279
0.7689 Intermediate Similarity NPC170751
0.7685 Intermediate Similarity NPC30570
0.7681 Intermediate Similarity NPC324245
0.7681 Intermediate Similarity NPC320748
0.7656 Intermediate Similarity NPC32451
0.7656 Intermediate Similarity NPC328559
0.7647 Intermediate Similarity NPC328928
0.7637 Intermediate Similarity NPC473833
0.7617 Intermediate Similarity NPC326930
0.7617 Intermediate Similarity NPC53255
0.7617 Intermediate Similarity NPC85879
0.7617 Intermediate Similarity NPC475301
0.7608 Intermediate Similarity NPC79223
0.7585 Intermediate Similarity NPC13603
0.7574 Intermediate Similarity NPC471015
0.7548 Intermediate Similarity NPC329024
0.7546 Intermediate Similarity NPC111732
0.7536 Intermediate Similarity NPC135950
0.7513 Intermediate Similarity NPC249614
0.7489 Intermediate Similarity NPC162812
0.7488 Intermediate Similarity NPC103230
0.7477 Intermediate Similarity NPC475835
0.7477 Intermediate Similarity NPC156044
0.7476 Intermediate Similarity NPC123395
0.7476 Intermediate Similarity NPC103361
0.7445 Intermediate Similarity NPC471004
0.7435 Intermediate Similarity NPC107287
0.7429 Intermediate Similarity NPC317672
0.7429 Intermediate Similarity NPC59033
0.7425 Intermediate Similarity NPC471013
0.7425 Intermediate Similarity NPC180668
0.7425 Intermediate Similarity NPC148896
0.7416 Intermediate Similarity NPC109922
0.7383 Intermediate Similarity NPC12944
0.7383 Intermediate Similarity NPC25442
0.7379 Intermediate Similarity NPC44354
0.7355 Intermediate Similarity NPC471978
0.735 Intermediate Similarity NPC476090
0.7324 Intermediate Similarity NPC155792
0.73 Intermediate Similarity NPC10904
0.73 Intermediate Similarity NPC191310
0.7265 Intermediate Similarity NPC471979
0.7227 Intermediate Similarity NPC318299
0.7225 Intermediate Similarity NPC112741
0.722 Intermediate Similarity NPC314270
0.7206 Intermediate Similarity NPC317010
0.7195 Intermediate Similarity NPC317752
0.719 Intermediate Similarity NPC471546
0.711 Intermediate Similarity NPC238457
0.7095 Intermediate Similarity NPC469489
0.7081 Intermediate Similarity NPC328798
0.7081 Intermediate Similarity NPC325775
0.7067 Intermediate Similarity NPC282103
0.7062 Intermediate Similarity NPC114974
0.7053 Intermediate Similarity NPC327373
0.7019 Intermediate Similarity NPC207851
0.6991 Remote Similarity NPC50997
0.6991 Remote Similarity NPC160127
0.699 Remote Similarity NPC164340
0.6982 Remote Similarity NPC314834
0.6974 Remote Similarity NPC253314
0.6944 Remote Similarity NPC149708
0.6938 Remote Similarity NPC46895
0.6937 Remote Similarity NPC472070
0.6933 Remote Similarity NPC37473
0.6916 Remote Similarity NPC141385
0.6909 Remote Similarity NPC327592
0.6906 Remote Similarity NPC123839
0.6901 Remote Similarity NPC138370
0.6901 Remote Similarity NPC127647
0.6895 Remote Similarity NPC143977
0.6893 Remote Similarity NPC84347
0.6891 Remote Similarity NPC159630
0.6891 Remote Similarity NPC230085
0.689 Remote Similarity NPC322043
0.689 Remote Similarity NPC325093
0.6889 Remote Similarity NPC221100

  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 NPC207531 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
0.8325 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD7396 Approved
0.7592 Intermediate Similarity NPD820 Phase 3
0.7328 Intermediate Similarity NPD7885 Phase 2
0.7328 Intermediate Similarity NPD7886 Phase 2
0.7285 Intermediate Similarity NPD3394 Approved
0.7285 Intermediate Similarity NPD3393 Approved
0.7285 Intermediate Similarity NPD3389 Approved
0.7252 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD8325 Phase 3
0.7252 Intermediate Similarity NPD8326 Phase 3
0.7246 Intermediate Similarity NPD8468 Phase 2
0.7225 Intermediate Similarity NPD9271 Approved
0.7222 Intermediate Similarity NPD2831 Approved
0.7222 Intermediate Similarity NPD3947 Discontinued
0.7202 Intermediate Similarity NPD2510 Approved
0.7202 Intermediate Similarity NPD2509 Approved
0.7172 Intermediate Similarity NPD5088 Discontinued
0.7169 Intermediate Similarity NPD4506 Discontinued
0.7164 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3795 Approved
0.7117 Intermediate Similarity NPD3794 Approved
0.7097 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6529 Discontinued
0.6979 Remote Similarity NPD5891 Approved
0.6963 Remote Similarity NPD5975 Clinical (unspecified phase)
0.696 Remote Similarity NPD6770 Approved
0.6959 Remote Similarity NPD1270 Approved
0.6955 Remote Similarity NPD7010 Phase 3
0.6951 Remote Similarity NPD4417 Approved
0.6947 Remote Similarity NPD4989 Phase 2
0.693 Remote Similarity NPD8479 Phase 2
0.692 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6911 Remote Similarity NPD107 Approved
0.69 Remote Similarity NPD4301 Approved
0.6866 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6856 Remote Similarity NPD3280 Approved
0.6854 Remote Similarity NPD8063 Discontinued
0.6838 Remote Similarity NPD4952 Phase 3
0.6833 Remote Similarity NPD1483 Discontinued
0.6803 Remote Similarity NPD6525 Clinical (unspecified phase)
0.68 Remote Similarity NPD5475 Discontinued
0.6781 Remote Similarity NPD5640 Discontinued
0.6779 Remote Similarity NPD6642 Approved
0.6779 Remote Similarity NPD6641 Approved
0.6774 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6771 Remote Similarity NPD3371 Approved
0.6769 Remote Similarity NPD9074 Approved
0.6769 Remote Similarity NPD9075 Approved
0.6765 Remote Similarity NPD3006 Discontinued
0.6751 Remote Similarity NPD4373 Phase 2
0.6749 Remote Similarity NPD6635 Approved
0.6744 Remote Similarity NPD2336 Approved
0.6736 Remote Similarity NPD8409 Suspended
0.6725 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6716 Remote Similarity NPD2582 Approved
0.6716 Remote Similarity NPD2581 Approved
0.6712 Remote Similarity NPD7777 Approved
0.6712 Remote Similarity NPD53 Approved
0.6712 Remote Similarity NPD7778 Approved
0.6696 Remote Similarity NPD7878 Phase 2
0.6694 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6682 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7404 Approved
0.6667 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6653 Remote Similarity NPD7708 Approved
0.6653 Remote Similarity NPD8370 Discontinued
0.6652 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6652 Remote Similarity NPD4500 Approved
0.6652 Remote Similarity NPD4501 Approved
0.6651 Remote Similarity NPD7234 Approved
0.6651 Remote Similarity NPD7233 Approved
0.665 Remote Similarity NPD2511 Approved
0.6638 Remote Similarity NPD7707 Approved
0.6638 Remote Similarity NPD8289 Discontinued
0.6636 Remote Similarity NPD4376 Phase 3
0.6624 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6621 Remote Similarity NPD2307 Discontinued
0.6614 Remote Similarity NPD7803 Approved
0.6609 Remote Similarity NPD8160 Phase 2
0.6606 Remote Similarity NPD4526 Approved
0.6606 Remote Similarity NPD4529 Approved
0.6606 Remote Similarity NPD4528 Approved
0.6605 Remote Similarity NPD8021 Approved
0.6605 Remote Similarity NPD8020 Approved
0.6599 Remote Similarity NPD5482 Discontinued
0.6581 Remote Similarity NPD8356 Approved
0.6577 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6575 Remote Similarity NPD4427 Phase 2
0.6567 Remote Similarity NPD1996 Discontinued
0.6559 Remote Similarity NPD4369 Phase 2
0.6555 Remote Similarity NPD5801 Clinical (unspecified phase)
0.655 Remote Similarity NPD7069 Discontinued
0.654 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6987 Phase 1
0.6533 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6528 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6527 Remote Similarity NPD6962 Phase 2
0.6522 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6518 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6517 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6512 Remote Similarity NPD4889 Approved
0.6507 Remote Similarity NPD7470 Discontinued
0.6504 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6504 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6504 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6502 Remote Similarity NPD6825 Phase 1
0.6484 Remote Similarity NPD6665 Discontinued
0.6475 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6471 Remote Similarity NPD8430 Approved
0.6471 Remote Similarity NPD4086 Phase 1
0.6471 Remote Similarity NPD6226 Phase 3
0.6468 Remote Similarity NPD6298 Discontinued
0.6463 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6462 Remote Similarity NPD2896 Discontinued
0.6462 Remote Similarity NPD1032 Phase 2
0.6458 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6458 Remote Similarity NPD7688 Phase 1
0.6456 Remote Similarity NPD3925 Approved
0.6453 Remote Similarity NPD6955 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6276 Discontinued
0.6452 Remote Similarity NPD4948 Discontinued
0.645 Remote Similarity NPD3217 Phase 2
0.6449 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6790 Phase 1
0.6447 Remote Similarity NPD7467 Discontinued
0.6445 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6443 Remote Similarity NPD8091 Phase 3
0.6432 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6479 Discontinued
0.6429 Remote Similarity NPD5228 Phase 3
0.6429 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4804 Approved
0.6417 Remote Similarity NPD5022 Discontinued
0.6417 Remote Similarity NPD7956 Approved
0.6417 Remote Similarity NPD7955 Approved
0.6416 Remote Similarity NPD5513 Phase 2
0.6416 Remote Similarity NPD6176 Phase 1
0.641 Remote Similarity NPD4429 Discontinued
0.641 Remote Similarity NPD1926 Approved
0.641 Remote Similarity NPD1623 Approved
0.6407 Remote Similarity NPD5866 Approved
0.6404 Remote Similarity NPD180 Clinical (unspecified phase)
0.6404 Remote Similarity NPD7562 Approved
0.6393 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6388 Remote Similarity NPD5901 Discontinued
0.6379 Remote Similarity NPD5888 Phase 2
0.6372 Remote Similarity NPD3178 Discontinued
0.6364 Remote Similarity NPD4805 Approved
0.6364 Remote Similarity NPD6446 Discontinued
0.636 Remote Similarity NPD7001 Phase 3
0.6359 Remote Similarity NPD1630 Approved
0.6357 Remote Similarity NPD5450 Discontinued
0.6352 Remote Similarity NPD5293 Phase 2
0.6345 Remote Similarity NPD8375 Approved
0.6333 Remote Similarity NPD1343 Approved
0.6333 Remote Similarity NPD6872 Clinical (unspecified phase)
0.633 Remote Similarity NPD5444 Phase 1
0.633 Remote Similarity NPD4375 Approved
0.6329 Remote Similarity NPD4923 Phase 1
0.6325 Remote Similarity NPD5490 Discontinued
0.6321 Remote Similarity NPD2077 Approved
0.6321 Remote Similarity NPD2076 Approved
0.632 Remote Similarity NPD5072 Discontinued
0.632 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6318 Remote Similarity NPD7269 Clinical (unspecified phase)
0.6313 Remote Similarity NPD1096 Discontinued
0.6311 Remote Similarity NPD8329 Phase 3
0.6306 Remote Similarity NPD1173 Approved
0.6306 Remote Similarity NPD6361 Phase 2
0.63 Remote Similarity NPD751 Clinical (unspecified phase)
0.6296 Remote Similarity NPD3386 Phase 2
0.6295 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6294 Remote Similarity NPD203 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6293 Remote Similarity NPD2809 Approved
0.6292 Remote Similarity NPD7426 Phase 1
0.6287 Remote Similarity NPD6242 Discontinued
0.6282 Remote Similarity NPD4667 Clinical (unspecified phase)
0.628 Remote Similarity NPD5255 Approved
0.6277 Remote Similarity NPD5583 Clinical (unspecified phase)
0.6274 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6271 Remote Similarity NPD6578 Clinical (unspecified phase)
0.627 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6268 Remote Similarity NPD1631 Approved
0.6266 Remote Similarity NPD8097 Phase 3
0.6266 Remote Similarity NPD8096 Phase 3
0.626 Remote Similarity NPD4926 Clinical (unspecified phase)
0.625 Remote Similarity NPD7576 Discontinued
0.625 Remote Similarity NPD7818 Clinical (unspecified phase)
0.625 Remote Similarity NPD1643 Phase 3
0.6245 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6245 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6244 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6244 Remote Similarity NPD2544 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6999 Discontinued
0.6239 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6239 Remote Similarity NPD3569 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