Structure

Physi-Chem Properties

Molecular Weight:  252.21
Volume:  294.963
LogP:  5.124
LogD:  2.835
LogS:  -4.432
# Rotatable Bonds:  11
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.424
Synthetic Accessibility Score:  2.207
Fsp3:  0.812
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.816
MDCK Permeability:  2.042264532065019e-05
Pgp-inhibitor:  0.348
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.99
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.273
Plasma Protein Binding (PPB):  97.66345977783203%
Volume Distribution (VD):  0.803
Pgp-substrate:  0.6964880228042603%

ADMET: Metabolism

CYP1A2-inhibitor:  0.476
CYP1A2-substrate:  0.202
CYP2C19-inhibitor:  0.612
CYP2C19-substrate:  0.318
CYP2C9-inhibitor:  0.459
CYP2C9-substrate:  0.99
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.085
CYP3A4-inhibitor:  0.084
CYP3A4-substrate:  0.025

ADMET: Excretion

Clearance (CL):  2.837
Half-life (T1/2):  0.773

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.041
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.04
Skin Sensitization:  0.929
Carcinogencity:  0.128
Eye Corrosion:  0.976
Eye Irritation:  0.975
Respiratory Toxicity:  0.826

Download Data

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

  Natural Product: NPC163746

Natural Product ID:  NPC163746
Common Name*:   6-Hexadecynoic Acid
IUPAC Name:   hexadec-6-ynoic acid
Synonyms:   6-Hexadecynoic Acid
Standard InCHIKey:  OMEMMZJIJNUXIH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-9,12-15H2,1H3,(H,17,18)
SMILES:  CCCCCCCCCC#CCCCCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1269413
PubChem CID:   49770727
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000262] Fatty acids and conjugates
          • [CHEMONTID:0002949] Long-chain fatty 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
NPO7415 Sommera sabiceoides Species Rubiaceae 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
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum IC50 = 3.6 ug.mL-1 PMID[506870]
NPT1332 Individual Protein Fatty acid synthase Plasmodium falciparum IC50 = 12.0 ug.mL-1 PMID[506870]
NPT1334 Individual Protein 3-oxoacyl-acyl-carrier protein reductase Plasmodium falciparum IC50 > 100.0 ug.mL-1 PMID[506870]
NPT839 Cell Line L6 Rattus norvegicus IC50 = 30.3 ug.mL-1 PMID[506870]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 22.5 ug.mL-1 PMID[506870]
NPT475 Organism Plasmodium yoelii Plasmodium yoelii IC50 > 25.0 ug.mL-1 PMID[506870]
NPT2 Others Unspecified Ratio IC50 = 10.0 n.a. PMID[506870]
NPT2 Others Unspecified Ratio IC50 = 50.0 n.a. PMID[506870]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 31.7 ug.mL-1 PMID[506870]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 30.0 ug.mL-1 PMID[506870]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 9.8 ug.mL-1 PMID[506870]
NPT20 Organism Candida albicans Candida albicans IC50 = 81800.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans IC50 = 85900.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans IC50 = 50300.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans MIC = 198100.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans IC50 = 56800.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans MIC = 99100.0 nM PMID[506871]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 1200.0 nM PMID[506871]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes IC50 = 2300.0 nM PMID[506871]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii IC50 = 2900.0 nM PMID[506871]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum IC50 = 3800.0 nM PMID[506871]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes IC50 = 3900.0 nM PMID[506871]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 4600.0 nM PMID[506871]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii MIC = 6200.0 nM PMID[506871]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MFC = 6.2 uM PMID[506871]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum IC50 = 8700.0 nM PMID[506871]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 9300.0 nM PMID[506871]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus IC50 = 9400.0 nM PMID[506871]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MFC = 12.4 uM PMID[506871]
NPT20 Organism Candida albicans Candida albicans IC50 = 23300.0 nM PMID[506871]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 24800.0 nM PMID[506871]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MFC = 24.8 uM PMID[506871]
NPT186 Organism Candida tropicalis Candida tropicalis IC50 = 29500.0 nM PMID[506871]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 31000.0 nM PMID[506871]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 37100.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans IC50 = 40500.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans IC50 = 47800.0 nM PMID[506871]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii MFC = 49.5 uM PMID[506871]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 49500.0 nM PMID[506871]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 52400.0 nM PMID[506871]
NPT186 Organism Candida tropicalis Candida tropicalis MIC = 74300.0 nM PMID[506871]
NPT186 Organism Candida tropicalis Candida tropicalis MFC = 99.1 uM PMID[506871]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC = 99.1 uM PMID[506871]
NPT21 Organism Aspergillus niger Aspergillus niger IC50 = 100900.0 nM PMID[506871]
NPT185 Organism Aspergillus flavus Aspergillus flavus IC50 = 105900.0 nM PMID[506871]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus IC50 = 165600.0 nM PMID[506871]
NPT20 Organism Candida albicans Candida albicans MFC = 198.1 uM PMID[506871]
NPT554 Organism Candida glabrata Candida glabrata IC50 > 198100.0 nM PMID[506871]
NPT188 Organism Candida parapsilosis Candida parapsilosis IC50 > 198100.0 nM PMID[506871]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MFC = 198.1 uM PMID[506871]
NPT185 Organism Aspergillus flavus Aspergillus flavus MIC = 198100.0 nM PMID[506871]
NPT185 Organism Aspergillus flavus Aspergillus flavus MFC = 198.1 uM PMID[506871]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MFC = 198.1 uM PMID[506871]

☑ 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 NPC163746 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 NPC103286
0.9744 High Similarity NPC301528
0.9744 High Similarity NPC71317
0.9744 High Similarity NPC129972
0.95 High Similarity NPC255837
0.95 High Similarity NPC19305
0.9268 High Similarity NPC8219
0.9211 High Similarity NPC73245
0.8947 High Similarity NPC158179
0.8537 High Similarity NPC171736
0.8537 High Similarity NPC209970
0.8537 High Similarity NPC307783
0.8537 High Similarity NPC196924
0.8537 High Similarity NPC216630
0.8537 High Similarity NPC149184
0.85 High Similarity NPC14227
0.85 High Similarity NPC154186
0.85 High Similarity NPC301696
0.85 High Similarity NPC301585
0.85 High Similarity NPC279026
0.85 High Similarity NPC261080
0.85 High Similarity NPC201844
0.85 High Similarity NPC113928
0.8444 Intermediate Similarity NPC304162
0.8333 Intermediate Similarity NPC67462
0.814 Intermediate Similarity NPC74845
0.8085 Intermediate Similarity NPC470412
0.8085 Intermediate Similarity NPC470410
0.8049 Intermediate Similarity NPC118968
0.8049 Intermediate Similarity NPC214610
0.8049 Intermediate Similarity NPC294085
0.8049 Intermediate Similarity NPC183424
0.7895 Intermediate Similarity NPC175342
0.7805 Intermediate Similarity NPC268826
0.7778 Intermediate Similarity NPC30195
0.7778 Intermediate Similarity NPC12438
0.775 Intermediate Similarity NPC155263
0.7708 Intermediate Similarity NPC100096
0.7674 Intermediate Similarity NPC325452
0.7674 Intermediate Similarity NPC248763
0.7609 Intermediate Similarity NPC21844
0.7609 Intermediate Similarity NPC328497
0.7609 Intermediate Similarity NPC324004
0.7556 Intermediate Similarity NPC55023
0.7551 Intermediate Similarity NPC18357
0.75 Intermediate Similarity NPC156630
0.7447 Intermediate Similarity NPC324793
0.7447 Intermediate Similarity NPC106872
0.7447 Intermediate Similarity NPC477878
0.7442 Intermediate Similarity NPC12156
0.7442 Intermediate Similarity NPC161097
0.7442 Intermediate Similarity NPC28598
0.7436 Intermediate Similarity NPC18224
0.7436 Intermediate Similarity NPC328710
0.7391 Intermediate Similarity NPC314679
0.7381 Intermediate Similarity NPC201622
0.7381 Intermediate Similarity NPC305660
0.7381 Intermediate Similarity NPC54980
0.7381 Intermediate Similarity NPC22903
0.7347 Intermediate Similarity NPC284212
0.7317 Intermediate Similarity NPC134782
0.7308 Intermediate Similarity NPC187777
0.7308 Intermediate Similarity NPC179764
0.7209 Intermediate Similarity NPC219536
0.7209 Intermediate Similarity NPC3531
0.7209 Intermediate Similarity NPC31551
0.7143 Intermediate Similarity NPC252843
0.7143 Intermediate Similarity NPC90904
0.7143 Intermediate Similarity NPC109026
0.7115 Intermediate Similarity NPC473863
0.7115 Intermediate Similarity NPC54766
0.7115 Intermediate Similarity NPC274290
0.7111 Intermediate Similarity NPC236579
0.7111 Intermediate Similarity NPC203531
0.7105 Intermediate Similarity NPC174368
0.7083 Intermediate Similarity NPC131770
0.7083 Intermediate Similarity NPC200618
0.7073 Intermediate Similarity NPC317203
0.7045 Intermediate Similarity NPC149299
0.7045 Intermediate Similarity NPC165533
0.7045 Intermediate Similarity NPC40597
0.7045 Intermediate Similarity NPC256163
0.7045 Intermediate Similarity NPC250028
0.7 Intermediate Similarity NPC28205
0.7 Intermediate Similarity NPC470411
0.6957 Remote Similarity NPC317128
0.6939 Remote Similarity NPC26253
0.6905 Remote Similarity NPC80396
0.6905 Remote Similarity NPC154642
0.6889 Remote Similarity NPC53541
0.6863 Remote Similarity NPC161366
0.6863 Remote Similarity NPC92114
0.6852 Remote Similarity NPC225929
0.6829 Remote Similarity NPC57499
0.6818 Remote Similarity NPC80234
0.6818 Remote Similarity NPC223249
0.6809 Remote Similarity NPC47363
0.6809 Remote Similarity NPC469781
0.6809 Remote Similarity NPC287231
0.6739 Remote Similarity NPC289686
0.6735 Remote Similarity NPC180534
0.6731 Remote Similarity NPC294548
0.6731 Remote Similarity NPC36061
0.6731 Remote Similarity NPC72722
0.6731 Remote Similarity NPC139029
0.6731 Remote Similarity NPC1813
0.6667 Remote Similarity NPC166287
0.6604 Remote Similarity NPC25417
0.6604 Remote Similarity NPC261831
0.6604 Remote Similarity NPC281972
0.6604 Remote Similarity NPC154245
0.6604 Remote Similarity NPC88966
0.6604 Remote Similarity NPC87564
0.6604 Remote Similarity NPC424
0.6604 Remote Similarity NPC469937
0.6604 Remote Similarity NPC320588
0.6604 Remote Similarity NPC32467
0.6604 Remote Similarity NPC23155
0.6604 Remote Similarity NPC6095
0.6604 Remote Similarity NPC290563
0.6604 Remote Similarity NPC53463
0.6604 Remote Similarity NPC87394
0.6604 Remote Similarity NPC85813
0.66 Remote Similarity NPC5413
0.66 Remote Similarity NPC149821
0.6596 Remote Similarity NPC76051
0.6538 Remote Similarity NPC281245
0.6531 Remote Similarity NPC42304
0.6522 Remote Similarity NPC474361
0.6512 Remote Similarity NPC80641
0.6491 Remote Similarity NPC235242
0.6481 Remote Similarity NPC45626
0.6471 Remote Similarity NPC59051
0.6471 Remote Similarity NPC50457
0.6444 Remote Similarity NPC81263
0.6441 Remote Similarity NPC226592
0.6429 Remote Similarity NPC127142
0.6429 Remote Similarity NPC329819
0.6429 Remote Similarity NPC7814
0.6429 Remote Similarity NPC267817
0.6429 Remote Similarity NPC154396
0.6415 Remote Similarity NPC321062
0.6415 Remote Similarity NPC70387
0.64 Remote Similarity NPC207292
0.6364 Remote Similarity NPC18951
0.6364 Remote Similarity NPC477201
0.6364 Remote Similarity NPC128996
0.6327 Remote Similarity NPC145045
0.6327 Remote Similarity NPC52700
0.6327 Remote Similarity NPC105329
0.6327 Remote Similarity NPC63182
0.6327 Remote Similarity NPC308301
0.6316 Remote Similarity NPC149209
0.6296 Remote Similarity NPC289979
0.6279 Remote Similarity NPC301398
0.6279 Remote Similarity NPC86545
0.6279 Remote Similarity NPC223374
0.6279 Remote Similarity NPC196442
0.6226 Remote Similarity NPC129458
0.6222 Remote Similarity NPC326532
0.62 Remote Similarity NPC326957
0.62 Remote Similarity NPC249754
0.619 Remote Similarity NPC286695
0.619 Remote Similarity NPC322892
0.619 Remote Similarity NPC125575
0.6167 Remote Similarity NPC470320
0.6154 Remote Similarity NPC224227
0.6154 Remote Similarity NPC55678
0.6122 Remote Similarity NPC273545
0.6111 Remote Similarity NPC10081
0.6111 Remote Similarity NPC225066
0.6098 Remote Similarity NPC168982
0.6087 Remote Similarity NPC471282
0.6078 Remote Similarity NPC216130
0.6078 Remote Similarity NPC91495
0.6047 Remote Similarity NPC286498
0.6042 Remote Similarity NPC144829
0.6038 Remote Similarity NPC262968
0.6038 Remote Similarity NPC287811
0.6034 Remote Similarity NPC469924
0.6034 Remote Similarity NPC470363
0.6034 Remote Similarity NPC274927
0.6034 Remote Similarity NPC106851
0.6032 Remote Similarity NPC82315
0.6 Remote Similarity NPC117572
0.6 Remote Similarity NPC74352
0.6 Remote Similarity NPC14608
0.6 Remote Similarity NPC295442
0.6 Remote Similarity NPC206924
0.5962 Remote Similarity NPC476469
0.5952 Remote Similarity NPC225318
0.5952 Remote Similarity NPC12904
0.5952 Remote Similarity NPC40965
0.5952 Remote Similarity NPC280532
0.5952 Remote Similarity NPC76608
0.5952 Remote Similarity NPC149101
0.5952 Remote Similarity NPC16578
0.5932 Remote Similarity NPC469921
0.5932 Remote Similarity NPC122521
0.5932 Remote Similarity NPC174447

  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 NPC163746 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
0.8537 High Similarity NPD2270 Approved
0.85 High Similarity NPD633 Phase 3
0.85 High Similarity NPD9448 Phase 2
0.8049 Intermediate Similarity NPD9655 Approved
0.7955 Intermediate Similarity NPD3199 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD3206 Approved
0.7442 Intermediate Similarity NPD9635 Discontinued
0.7391 Intermediate Similarity NPD634 Phase 3
0.7209 Intermediate Similarity NPD9450 Approved
0.7209 Intermediate Similarity NPD77 Approved
0.6863 Remote Similarity NPD3186 Phase 1
0.6809 Remote Similarity NPD2699 Approved
0.6744 Remote Similarity NPD9449 Clinical (unspecified phase)
0.6739 Remote Similarity NPD387 Clinical (unspecified phase)
0.6735 Remote Similarity NPD622 Approved
0.6735 Remote Similarity NPD2266 Phase 2
0.6731 Remote Similarity NPD3172 Approved
0.6667 Remote Similarity NPD9431 Approved
0.6667 Remote Similarity NPD9430 Approved
0.6604 Remote Similarity NPD3194 Approved
0.6604 Remote Similarity NPD3195 Phase 2
0.6604 Remote Similarity NPD4266 Approved
0.6604 Remote Similarity NPD3730 Approved
0.6604 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6604 Remote Similarity NPD3196 Approved
0.6604 Remote Similarity NPD3728 Approved
0.66 Remote Similarity NPD3173 Approved
0.6429 Remote Similarity NPD8857 Approved
0.6296 Remote Similarity NPD615 Clinical (unspecified phase)
0.6279 Remote Similarity NPD9447 Approved
0.6222 Remote Similarity NPD9513 Phase 1
0.6078 Remote Similarity NPD6125 Clinical (unspecified phase)
0.6038 Remote Similarity NPD28 Approved
0.6038 Remote Similarity NPD9638 Phase 2
0.6038 Remote Similarity NPD29 Approved
0.6034 Remote Similarity NPD3198 Approved
0.6 Remote Similarity NPD4222 Approved
0.6 Remote Similarity NPD3174 Discontinued
0.5918 Remote Similarity NPD9019 Approved
0.5814 Remote Similarity NPD5383 Approved
0.5814 Remote Similarity NPD2272 Approved
0.5686 Remote Similarity NPD39 Approved
0.566 Remote Similarity NPD9016 Clinical (unspecified phase)
0.5645 Remote Similarity NPD3197 Phase 1
0.5645 Remote Similarity NPD7909 Approved
0.5614 Remote Similarity NPD9454 Approved

  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