Structure

Physi-Chem Properties

Molecular Weight:  740.33
Volume:  719.175
LogP:  2.963
LogD:  1.545
LogS:  -4.042
# Rotatable Bonds:  13
TPSA:  216.86
# H-Bond Aceptor:  16
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.214
Synthetic Accessibility Score:  6.921
Fsp3:  0.806
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:  -5.268
MDCK Permeability:  0.00011627611092990264
Pgp-inhibitor:  1.0
Pgp-substrate:  0.05
Human Intestinal Absorption (HIA):  0.815
20% Bioavailability (F20%):  0.068
30% Bioavailability (F30%):  0.706

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.08
Plasma Protein Binding (PPB):  44.959659576416016%
Volume Distribution (VD):  1.409
Pgp-substrate:  30.448875427246094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.013
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.008
CYP2D6-inhibitor:  0.718
CYP2D6-substrate:  0.037
CYP3A4-inhibitor:  0.46
CYP3A4-substrate:  0.289

ADMET: Excretion

Clearance (CL):  2.92
Half-life (T1/2):  0.917

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.968
Drug-inuced Liver Injury (DILI):  0.928
AMES Toxicity:  0.032
Rat Oral Acute Toxicity:  0.308
Maximum Recommended Daily Dose:  0.009
Skin Sensitization:  0.104
Carcinogencity:  0.03
Eye Corrosion:  0.027
Eye Irritation:  0.023
Respiratory Toxicity:  0.011

Download Data

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

  Natural Product: NPC470191

Natural Product ID:  NPC470191
Common Name*:   Salicinolide
IUPAC Name:   n.a.
Synonyms:   Salicinolide
Standard InCHIKey:  WVAYGRRRXZJRLY-XEIURFSESA-N
Standard InCHI:  InChI=1S/C36H52O16/c1-16(2)14-45-32-26(46-18(4)37)31-33(9,10)30-25(50-30)17(3)27(43)36(52-22(8)41)15-34(11,51-21(7)40)28(47-19(5)38)24(36)29(48-20(6)39)35(32,44)13-12-23(42)49-31/h16-17,24-26,28-32,44H,12-15H2,1-11H3/t17-,24-,25-,26+,28-,29-,30+,31-,32-,34-,35-,36-/m1/s1
SMILES:  CC(CO[C@@H]1[C@@H](OC(=O)C)[C@H]2OC(=O)CC[C@@]1(O)[C@H](OC(=O)C)[C@@H]1[C@](OC(=O)C)(C[C@@]([C@@H]1OC(=O)C)(C)OC(=O)C)C(=O)[C@@H]([C@@H]1[C@@H](C2(C)C)O1)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1812480
PubChem CID:   56659231
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002967] Hexacarboxylic acids 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
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]
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]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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 = 5.3 % PMID[479529]
NPT2738 Cell Line Ishikawa Homo sapiens GI = 31.5 % PMID[479529]
NPT83 Cell Line MCF7 Homo sapiens GI = 24.8 % PMID[479529]
NPT165 Cell Line HeLa Homo sapiens GI = 20.8 % PMID[479529]
NPT2738 Cell Line Ishikawa Homo sapiens GI = 33.0 % PMID[479529]
NPT83 Cell Line MCF7 Homo sapiens GI = 29.2 % PMID[479529]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 5.9 n.a. PMID[479529]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 17.5 n.a. PMID[479529]

☑ 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 NPC470191 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
0.8211 Intermediate Similarity NPC474699
0.82 Intermediate Similarity NPC250594
0.81 Intermediate Similarity NPC471767
0.7788 Intermediate Similarity NPC168890
0.7706 Intermediate Similarity NPC470116
0.7706 Intermediate Similarity NPC470115
0.7692 Intermediate Similarity NPC177518
0.7692 Intermediate Similarity NPC132304
0.7692 Intermediate Similarity NPC154962
0.7692 Intermediate Similarity NPC88890
0.7692 Intermediate Similarity NPC114365
0.7692 Intermediate Similarity NPC18433
0.7692 Intermediate Similarity NPC169089
0.7692 Intermediate Similarity NPC123070
0.7692 Intermediate Similarity NPC18044
0.7685 Intermediate Similarity NPC98870
0.7658 Intermediate Similarity NPC475401
0.7642 Intermediate Similarity NPC220773
0.7642 Intermediate Similarity NPC278693
0.7634 Intermediate Similarity NPC212340
0.7589 Intermediate Similarity NPC477092
0.7568 Intermediate Similarity NPC475305
0.75 Intermediate Similarity NPC49393
0.75 Intermediate Similarity NPC182185
0.75 Intermediate Similarity NPC292803
0.7477 Intermediate Similarity NPC329876
0.7477 Intermediate Similarity NPC167044
0.7473 Intermediate Similarity NPC214030
0.7473 Intermediate Similarity NPC83108
0.7453 Intermediate Similarity NPC474101
0.7451 Intermediate Similarity NPC278028
0.7451 Intermediate Similarity NPC328180
0.7407 Intermediate Similarity NPC217041
0.7404 Intermediate Similarity NPC259654
0.7404 Intermediate Similarity NPC298266
0.7383 Intermediate Similarity NPC176756
0.7379 Intermediate Similarity NPC274695
0.7374 Intermediate Similarity NPC65359
0.7368 Intermediate Similarity NPC157328
0.7364 Intermediate Similarity NPC475277
0.7364 Intermediate Similarity NPC473522
0.7364 Intermediate Similarity NPC477093
0.7333 Intermediate Similarity NPC78127
0.7333 Intermediate Similarity NPC105725
0.7333 Intermediate Similarity NPC471757
0.7327 Intermediate Similarity NPC470423
0.7315 Intermediate Similarity NPC117604
0.729 Intermediate Similarity NPC228311
0.729 Intermediate Similarity NPC469441
0.729 Intermediate Similarity NPC41674
0.7273 Intermediate Similarity NPC475495
0.7245 Intermediate Similarity NPC31349
0.7228 Intermediate Similarity NPC476189
0.7222 Intermediate Similarity NPC469788
0.7222 Intermediate Similarity NPC469787
0.7222 Intermediate Similarity NPC290247
0.7212 Intermediate Similarity NPC470188
0.7212 Intermediate Similarity NPC253995
0.717 Intermediate Similarity NPC470172
0.7157 Intermediate Similarity NPC206878
0.7143 Intermediate Similarity NPC97002
0.7143 Intermediate Similarity NPC470657
0.7129 Intermediate Similarity NPC469627
0.7117 Intermediate Similarity NPC473062
0.7111 Intermediate Similarity NPC96322
0.7105 Intermediate Similarity NPC179429
0.7103 Intermediate Similarity NPC471253
0.7103 Intermediate Similarity NPC469350
0.7103 Intermediate Similarity NPC473406
0.7097 Intermediate Similarity NPC474003
0.7091 Intermediate Similarity NPC208333
0.7091 Intermediate Similarity NPC227879
0.7087 Intermediate Similarity NPC287354
0.7087 Intermediate Similarity NPC62407
0.7087 Intermediate Similarity NPC322188
0.7087 Intermediate Similarity NPC470031
0.7087 Intermediate Similarity NPC17336
0.7075 Intermediate Similarity NPC178853
0.7059 Intermediate Similarity NPC228700
0.7048 Intermediate Similarity NPC476294
0.7037 Intermediate Similarity NPC473701
0.7037 Intermediate Similarity NPC327093
0.7037 Intermediate Similarity NPC473526
0.703 Intermediate Similarity NPC477444
0.703 Intermediate Similarity NPC477433
0.703 Intermediate Similarity NPC477442
0.7021 Intermediate Similarity NPC470014
0.7019 Intermediate Similarity NPC116683
0.7018 Intermediate Similarity NPC475490
0.701 Intermediate Similarity NPC472847
0.7 Intermediate Similarity NPC470009
0.7 Intermediate Similarity NPC477614
0.7 Intermediate Similarity NPC226491
0.7 Intermediate Similarity NPC316930
0.699 Remote Similarity NPC470424
0.699 Remote Similarity NPC329713
0.699 Remote Similarity NPC217567
0.699 Remote Similarity NPC76136
0.699 Remote Similarity NPC477495
0.6981 Remote Similarity NPC186861
0.6972 Remote Similarity NPC44004
0.697 Remote Similarity NPC476717
0.697 Remote Similarity NPC64862
0.6966 Remote Similarity NPC319007
0.6964 Remote Similarity NPC472003
0.6964 Remote Similarity NPC469824
0.6961 Remote Similarity NPC216137
0.6957 Remote Similarity NPC477867
0.6957 Remote Similarity NPC215030
0.6937 Remote Similarity NPC321661
0.6937 Remote Similarity NPC320475
0.6937 Remote Similarity NPC228190
0.6937 Remote Similarity NPC236753
0.6931 Remote Similarity NPC477440
0.6931 Remote Similarity NPC477443
0.6916 Remote Similarity NPC162024
0.6916 Remote Similarity NPC477356
0.6915 Remote Similarity NPC108014
0.6909 Remote Similarity NPC470192
0.6909 Remote Similarity NPC203974
0.6907 Remote Similarity NPC477936
0.6903 Remote Similarity NPC477489
0.6893 Remote Similarity NPC475488
0.6893 Remote Similarity NPC474379
0.6889 Remote Similarity NPC98711
0.6887 Remote Similarity NPC477355
0.6887 Remote Similarity NPC211087
0.6882 Remote Similarity NPC179922
0.6881 Remote Similarity NPC88469
0.6869 Remote Similarity NPC473350
0.6863 Remote Similarity NPC246173
0.6854 Remote Similarity NPC286842
0.6852 Remote Similarity NPC471254
0.6847 Remote Similarity NPC472079
0.6842 Remote Similarity NPC475616
0.6837 Remote Similarity NPC259173
0.6833 Remote Similarity NPC169818
0.6832 Remote Similarity NPC191221
0.6822 Remote Similarity NPC471381
0.6818 Remote Similarity NPC291643
0.6814 Remote Similarity NPC287311
0.6814 Remote Similarity NPC470281
0.68 Remote Similarity NPC477441
0.68 Remote Similarity NPC92139
0.68 Remote Similarity NPC469626
0.68 Remote Similarity NPC475491
0.6792 Remote Similarity NPC471241
0.6792 Remote Similarity NPC87090
0.6789 Remote Similarity NPC329704
0.6789 Remote Similarity NPC34562
0.6768 Remote Similarity NPC291310
0.6768 Remote Similarity NPC475689
0.6762 Remote Similarity NPC215570
0.6762 Remote Similarity NPC475900
0.6754 Remote Similarity NPC477492
0.675 Remote Similarity NPC267822
0.6739 Remote Similarity NPC470243
0.6735 Remote Similarity NPC242771
0.6735 Remote Similarity NPC164289
0.6735 Remote Similarity NPC477935
0.6735 Remote Similarity NPC311642
0.6735 Remote Similarity NPC100366
0.6733 Remote Similarity NPC314364
0.6733 Remote Similarity NPC239938
0.6731 Remote Similarity NPC470187
0.6731 Remote Similarity NPC475788
0.6727 Remote Similarity NPC310586
0.6727 Remote Similarity NPC470167
0.6726 Remote Similarity NPC50223
0.6703 Remote Similarity NPC475062
0.6702 Remote Similarity NPC228411
0.6701 Remote Similarity NPC472853
0.67 Remote Similarity NPC51267
0.6698 Remote Similarity NPC76862
0.6698 Remote Similarity NPC476728
0.6698 Remote Similarity NPC477354
0.6698 Remote Similarity NPC470883
0.6698 Remote Similarity NPC477264
0.6698 Remote Similarity NPC158416
0.6698 Remote Similarity NPC39859
0.6698 Remote Similarity NPC476009
0.6697 Remote Similarity NPC118405
0.6696 Remote Similarity NPC169888
0.6696 Remote Similarity NPC55972
0.6696 Remote Similarity NPC327286
0.6696 Remote Similarity NPC469826
0.6695 Remote Similarity NPC473203
0.6667 Remote Similarity NPC196528
0.6667 Remote Similarity NPC474266
0.6667 Remote Similarity NPC65858
0.6667 Remote Similarity NPC474100
0.6667 Remote Similarity NPC166079
0.6667 Remote Similarity NPC475232
0.6667 Remote Similarity NPC53158
0.6667 Remote Similarity NPC9303
0.6667 Remote Similarity NPC473775
0.6667 Remote Similarity NPC54737
0.6667 Remote Similarity NPC306776
0.6667 Remote Similarity NPC51249
0.6667 Remote Similarity NPC157476

  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 NPC470191 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
0.7692 Intermediate Similarity NPD4057 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD4056 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD1700 Approved
0.6667 Remote Similarity NPD4238 Approved
0.6667 Remote Similarity NPD4802 Phase 2
0.6639 Remote Similarity NPD6319 Approved
0.646 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7909 Approved
0.6325 Remote Similarity NPD8297 Approved
0.632 Remote Similarity NPD8293 Discontinued
0.6293 Remote Similarity NPD6371 Approved
0.629 Remote Similarity NPD7492 Approved
0.627 Remote Similarity NPD7736 Approved
0.6261 Remote Similarity NPD5345 Clinical (unspecified phase)
0.624 Remote Similarity NPD6616 Approved
0.6238 Remote Similarity NPD6435 Approved
0.623 Remote Similarity NPD6054 Approved
0.623 Remote Similarity NPD6059 Approved
0.6207 Remote Similarity NPD6372 Approved
0.6207 Remote Similarity NPD6373 Approved
0.619 Remote Similarity NPD7078 Approved
0.6186 Remote Similarity NPD3702 Approved
0.6129 Remote Similarity NPD6370 Approved
0.6106 Remote Similarity NPD8301 Approved
0.6106 Remote Similarity NPD8300 Approved
0.6106 Remote Similarity NPD8138 Approved
0.6106 Remote Similarity NPD8139 Approved
0.6106 Remote Similarity NPD8085 Approved
0.6106 Remote Similarity NPD8084 Approved
0.6106 Remote Similarity NPD8086 Approved
0.6106 Remote Similarity NPD8082 Approved
0.6106 Remote Similarity NPD8083 Approved
0.6102 Remote Similarity NPD6650 Approved
0.6102 Remote Similarity NPD6649 Approved
0.6087 Remote Similarity NPD6402 Approved
0.6087 Remote Similarity NPD7128 Approved
0.6087 Remote Similarity NPD5739 Approved
0.6087 Remote Similarity NPD8393 Approved
0.6087 Remote Similarity NPD6675 Approved
0.6067 Remote Similarity NPD3198 Approved
0.6053 Remote Similarity NPD8276 Approved
0.6053 Remote Similarity NPD8275 Approved
0.6048 Remote Similarity NPD6015 Approved
0.6048 Remote Similarity NPD6016 Approved
0.604 Remote Similarity NPD5368 Approved
0.6019 Remote Similarity NPD7983 Approved
0.6 Remote Similarity NPD4632 Approved
0.6 Remote Similarity NPD8081 Approved
0.6 Remote Similarity NPD5988 Approved
0.5984 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5983 Remote Similarity NPD6881 Approved
0.5983 Remote Similarity NPD6899 Approved
0.5983 Remote Similarity NPD7320 Approved
0.598 Remote Similarity NPD5369 Approved
0.5966 Remote Similarity NPD8130 Phase 1
0.5952 Remote Similarity NPD7604 Phase 2
0.5952 Remote Similarity NPD8328 Phase 3
0.5917 Remote Similarity NPD6882 Approved
0.5897 Remote Similarity NPD5697 Approved
0.5897 Remote Similarity NPD5701 Approved
0.5893 Remote Similarity NPD6083 Phase 2
0.5893 Remote Similarity NPD6084 Phase 2
0.5882 Remote Similarity NPD7102 Approved
0.5882 Remote Similarity NPD7290 Approved
0.5882 Remote Similarity NPD4634 Approved
0.5882 Remote Similarity NPD6883 Approved
0.5876 Remote Similarity NPD5777 Approved
0.5868 Remote Similarity NPD8133 Approved
0.5856 Remote Similarity NPD5695 Phase 3
0.5854 Remote Similarity NPD6009 Approved
0.5849 Remote Similarity NPD5786 Approved
0.5842 Remote Similarity NPD6115 Approved
0.5842 Remote Similarity NPD6118 Approved
0.5842 Remote Similarity NPD6114 Approved
0.5842 Remote Similarity NPD6697 Approved
0.5841 Remote Similarity NPD5696 Approved
0.5833 Remote Similarity NPD6847 Approved
0.5833 Remote Similarity NPD6869 Approved
0.5833 Remote Similarity NPD6617 Approved
0.5812 Remote Similarity NPD6008 Approved
0.5798 Remote Similarity NPD6013 Approved
0.5798 Remote Similarity NPD6014 Approved
0.5798 Remote Similarity NPD6012 Approved
0.5794 Remote Similarity NPD5983 Phase 2
0.5794 Remote Similarity NPD6921 Approved
0.5784 Remote Similarity NPD7329 Approved
0.5769 Remote Similarity NPD6033 Approved
0.5766 Remote Similarity NPD5282 Discontinued
0.5743 Remote Similarity NPD6116 Phase 1
0.5736 Remote Similarity NPD6336 Discontinued
0.573 Remote Similarity NPD73 Approved
0.5725 Remote Similarity NPD7319 Approved
0.5714 Remote Similarity NPD6011 Approved
0.5702 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5669 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5644 Remote Similarity NPD6117 Approved
0.5636 Remote Similarity NPD6698 Approved
0.5636 Remote Similarity NPD46 Approved
0.5636 Remote Similarity NPD5785 Approved
0.563 Remote Similarity NPD8140 Approved
0.563 Remote Similarity NPD8307 Discontinued
0.563 Remote Similarity NPD6412 Phase 2
0.5625 Remote Similarity NPD896 Approved
0.5625 Remote Similarity NPD898 Approved
0.5625 Remote Similarity NPD8080 Discontinued
0.5625 Remote Similarity NPD897 Approved
0.5619 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5619 Remote Similarity NPD4269 Approved
0.5619 Remote Similarity NPD4270 Approved
0.5615 Remote Similarity NPD7507 Approved
0.5612 Remote Similarity NPD4245 Approved
0.5612 Remote Similarity NPD4244 Approved
0.5612 Remote Similarity NPD4789 Approved
0.56 Remote Similarity NPD6113 Clinical (unspecified phase)
0.56 Remote Similarity NPD7115 Discovery

  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