Structure

Physi-Chem Properties

Molecular Weight:  578.31
Volume:  597.066
LogP:  1.346
LogD:  1.369
LogS:  -3.81
# Rotatable Bonds:  4
TPSA:  155.14
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.314
Synthetic Accessibility Score:  5.632
Fsp3:  0.581
Lipinski Rule-of-5:  Accepted
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:  -5.19
MDCK Permeability:  4.194099165033549e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.231
20% Bioavailability (F20%):  0.914
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.152
Plasma Protein Binding (PPB):  89.18187713623047%
Volume Distribution (VD):  0.655
Pgp-substrate:  5.2439422607421875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.057
CYP2C19-inhibitor:  0.06
CYP2C19-substrate:  0.524
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.829
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.755
CYP3A4-inhibitor:  0.575
CYP3A4-substrate:  0.125

ADMET: Excretion

Clearance (CL):  1.266
Half-life (T1/2):  0.665

ADMET: Toxicity

hERG Blockers:  0.806
Human Hepatotoxicity (H-HT):  0.917
Drug-inuced Liver Injury (DILI):  0.034
AMES Toxicity:  0.534
Rat Oral Acute Toxicity:  0.08
Maximum Recommended Daily Dose:  0.991
Skin Sensitization:  0.975
Carcinogencity:  0.591
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.958

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

  Natural Product: NPC251026

Natural Product ID:  NPC251026
Common Name*:   Gageomacrolactin 2
IUPAC Name:   (3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24R)-14-hydroxy-16-methoxy-24-methyl-8-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one
Synonyms:  
Standard InCHIKey:  RQTSCDVSKIOZMR-DEKVHSLYSA-N
Standard InCHI:  InChI=1S/C31H46O10/c1-22-14-8-4-3-5-10-18-25(38-2)20-23(33)15-9-6-11-16-24(17-12-7-13-19-27(34)39-22)40-31-30(37)29(36)28(35)26(21-32)41-31/h3,5-7,9-13,16,18-19,22-26,28-33,35-37H,4,8,14-15,17,20-21H2,1-2H3/b5-3+,9-6-,12-7+,16-11+,18-10+,19-13-/t22-,23+,24-,25+,26+,28+,29-,30+,31+/m1/s1
SMILES:  CO[C@H]1/C=C/C=C/CCC[C@@H](C)OC(=O)/C=CC=CC[C@@H](/C=C/C=CC[C@@H](C1)O)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2289502
PubChem CID:   76320318
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[11112781]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[153409]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[21673922]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23265519]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23317005]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23488669]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[27524650]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[29115831]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[31287310]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria 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
NPT306 Cell Line PC-3 Homo sapiens GI50 > 30.0 ug.mL-1 PMID[545168]
NPT2477 Cell Line NUGC-3 Homo sapiens GI50 > 30.0 ug.mL-1 PMID[545168]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 > 30.0 ug.mL-1 PMID[545168]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 > 30.0 ug.mL-1 PMID[545168]
NPT148 Cell Line HCT-15 Homo sapiens GI50 > 30.0 ug.mL-1 PMID[545168]
NPT369 Cell Line ACHN Homo sapiens GI50 > 30.0 ug.mL-1 PMID[545168]

☑ 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 NPC251026 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
0.987 High Similarity NPC142111
0.987 High Similarity NPC473315
0.9744 High Similarity NPC473308
0.95 High Similarity NPC208473
0.9359 High Similarity NPC469469
0.9268 High Similarity NPC470137
0.9048 High Similarity NPC473311
0.8916 High Similarity NPC118077
0.8916 High Similarity NPC475186
0.878 High Similarity NPC266718
0.8718 High Similarity NPC326661
0.8706 High Similarity NPC285588
0.8675 High Similarity NPC470124
0.8554 High Similarity NPC475035
0.8519 High Similarity NPC163362
0.8519 High Similarity NPC127295
0.8506 High Similarity NPC110072
0.8471 Intermediate Similarity NPC475037
0.8462 Intermediate Similarity NPC472173
0.8395 Intermediate Similarity NPC180725
0.8391 Intermediate Similarity NPC327253
0.8375 Intermediate Similarity NPC474026
0.8315 Intermediate Similarity NPC294293
0.8312 Intermediate Similarity NPC476012
0.8295 Intermediate Similarity NPC469410
0.8293 Intermediate Similarity NPC470147
0.8293 Intermediate Similarity NPC133226
0.8272 Intermediate Similarity NPC248775
0.8272 Intermediate Similarity NPC133377
0.8235 Intermediate Similarity NPC475034
0.8228 Intermediate Similarity NPC472174
0.8202 Intermediate Similarity NPC238090
0.8202 Intermediate Similarity NPC472195
0.8202 Intermediate Similarity NPC472196
0.8202 Intermediate Similarity NPC320552
0.8182 Intermediate Similarity NPC118078
0.8172 Intermediate Similarity NPC154132
0.8172 Intermediate Similarity NPC475157
0.8172 Intermediate Similarity NPC475655
0.8172 Intermediate Similarity NPC471637
0.8172 Intermediate Similarity NPC2313
0.8172 Intermediate Similarity NPC57586
0.8171 Intermediate Similarity NPC1180
0.8171 Intermediate Similarity NPC470148
0.8171 Intermediate Similarity NPC470149
0.8148 Intermediate Similarity NPC110813
0.8111 Intermediate Similarity NPC159698
0.8101 Intermediate Similarity NPC132938
0.8101 Intermediate Similarity NPC329914
0.8077 Intermediate Similarity NPC476037
0.8022 Intermediate Similarity NPC170204
0.8 Intermediate Similarity NPC197736
0.7952 Intermediate Similarity NPC179933
0.7927 Intermediate Similarity NPC233071
0.7901 Intermediate Similarity NPC327041
0.7901 Intermediate Similarity NPC285840
0.7889 Intermediate Similarity NPC477749
0.7875 Intermediate Similarity NPC185186
0.7875 Intermediate Similarity NPC329890
0.7875 Intermediate Similarity NPC327383
0.7865 Intermediate Similarity NPC477748
0.7848 Intermediate Similarity NPC474078
0.7835 Intermediate Similarity NPC315070
0.7831 Intermediate Similarity NPC477314
0.7805 Intermediate Similarity NPC188860
0.7805 Intermediate Similarity NPC229655
0.7802 Intermediate Similarity NPC61201
0.7792 Intermediate Similarity NPC146811
0.7778 Intermediate Similarity NPC202886
0.7778 Intermediate Similarity NPC6414
0.7778 Intermediate Similarity NPC303451
0.7778 Intermediate Similarity NPC107654
0.7765 Intermediate Similarity NPC236649
0.7765 Intermediate Similarity NPC21693
0.7763 Intermediate Similarity NPC294813
0.7763 Intermediate Similarity NPC13143
0.775 Intermediate Similarity NPC475762
0.7742 Intermediate Similarity NPC288350
0.7742 Intermediate Similarity NPC173329
0.7717 Intermediate Similarity NPC256368
0.7711 Intermediate Similarity NPC475711
0.7662 Intermediate Similarity NPC19769
0.7654 Intermediate Similarity NPC284006
0.764 Intermediate Similarity NPC313658
0.764 Intermediate Similarity NPC316138
0.7634 Intermediate Similarity NPC469543
0.7614 Intermediate Similarity NPC471494
0.76 Intermediate Similarity NPC133625
0.7595 Intermediate Similarity NPC63873
0.7586 Intermediate Similarity NPC470313
0.7586 Intermediate Similarity NPC156089
0.7586 Intermediate Similarity NPC473500
0.7586 Intermediate Similarity NPC38295
0.7579 Intermediate Similarity NPC203627
0.7564 Intermediate Similarity NPC201356
0.7564 Intermediate Similarity NPC276299
0.7561 Intermediate Similarity NPC315843
0.7558 Intermediate Similarity NPC184208
0.7558 Intermediate Similarity NPC8538
0.7558 Intermediate Similarity NPC280367
0.7553 Intermediate Similarity NPC306041
0.7532 Intermediate Similarity NPC148233
0.7532 Intermediate Similarity NPC25747
0.7531 Intermediate Similarity NPC293114
0.7528 Intermediate Similarity NPC311163
0.7526 Intermediate Similarity NPC201191
0.75 Intermediate Similarity NPC9447
0.75 Intermediate Similarity NPC288471
0.7474 Intermediate Similarity NPC475332
0.7439 Intermediate Similarity NPC55652
0.7436 Intermediate Similarity NPC96414
0.7423 Intermediate Similarity NPC219038
0.7419 Intermediate Similarity NPC320089
0.7391 Intermediate Similarity NPC471569
0.7391 Intermediate Similarity NPC117596
0.7391 Intermediate Similarity NPC177668
0.7386 Intermediate Similarity NPC315559
0.7375 Intermediate Similarity NPC475760
0.7368 Intermediate Similarity NPC255410
0.7363 Intermediate Similarity NPC137368
0.7356 Intermediate Similarity NPC315731
0.7349 Intermediate Similarity NPC477305
0.7349 Intermediate Similarity NPC477312
0.7349 Intermediate Similarity NPC477313
0.7349 Intermediate Similarity NPC477309
0.7349 Intermediate Similarity NPC477316
0.7349 Intermediate Similarity NPC477304
0.7349 Intermediate Similarity NPC477308
0.7349 Intermediate Similarity NPC477315
0.7347 Intermediate Similarity NPC13171
0.7347 Intermediate Similarity NPC195510
0.7347 Intermediate Similarity NPC222062
0.7347 Intermediate Similarity NPC471599
0.7342 Intermediate Similarity NPC124586
0.7333 Intermediate Similarity NPC47937
0.7326 Intermediate Similarity NPC139712
0.7326 Intermediate Similarity NPC321728
0.732 Intermediate Similarity NPC255677
0.732 Intermediate Similarity NPC22149
0.732 Intermediate Similarity NPC306344
0.732 Intermediate Similarity NPC244878
0.7317 Intermediate Similarity NPC316185
0.7312 Intermediate Similarity NPC472125
0.7312 Intermediate Similarity NPC472126
0.7312 Intermediate Similarity NPC472124
0.7312 Intermediate Similarity NPC472197
0.7312 Intermediate Similarity NPC472199
0.7308 Intermediate Similarity NPC31496
0.7308 Intermediate Similarity NPC287075
0.73 Intermediate Similarity NPC82251
0.7292 Intermediate Similarity NPC120299
0.7283 Intermediate Similarity NPC133450
0.7273 Intermediate Similarity NPC234304
0.7273 Intermediate Similarity NPC26810
0.7273 Intermediate Similarity NPC118761
0.7273 Intermediate Similarity NPC267869
0.7273 Intermediate Similarity NPC284929
0.7273 Intermediate Similarity NPC313677
0.7273 Intermediate Similarity NPC197541
0.7263 Intermediate Similarity NPC300710
0.7262 Intermediate Similarity NPC477306
0.7253 Intermediate Similarity NPC199382
0.7253 Intermediate Similarity NPC45409
0.7253 Intermediate Similarity NPC125142
0.7245 Intermediate Similarity NPC198992
0.7245 Intermediate Similarity NPC20673
0.7245 Intermediate Similarity NPC28304
0.7245 Intermediate Similarity NPC298255
0.7234 Intermediate Similarity NPC473561
0.7234 Intermediate Similarity NPC473723
0.7234 Intermediate Similarity NPC475173
0.7234 Intermediate Similarity NPC473663
0.7229 Intermediate Similarity NPC477311
0.7229 Intermediate Similarity NPC477303
0.7222 Intermediate Similarity NPC73166
0.7222 Intermediate Similarity NPC182383
0.7216 Intermediate Similarity NPC151093
0.7216 Intermediate Similarity NPC198422
0.7216 Intermediate Similarity NPC40182
0.7216 Intermediate Similarity NPC65700
0.7216 Intermediate Similarity NPC475653
0.7212 Intermediate Similarity NPC470025
0.7212 Intermediate Similarity NPC328074
0.7212 Intermediate Similarity NPC317460
0.7212 Intermediate Similarity NPC321272
0.7209 Intermediate Similarity NPC182292
0.7204 Intermediate Similarity NPC473904
0.7204 Intermediate Similarity NPC3952
0.7204 Intermediate Similarity NPC307699
0.7204 Intermediate Similarity NPC475995
0.7204 Intermediate Similarity NPC474098
0.72 Intermediate Similarity NPC86095
0.72 Intermediate Similarity NPC469869
0.7191 Intermediate Similarity NPC27314
0.7191 Intermediate Similarity NPC286770
0.7191 Intermediate Similarity NPC229799
0.7191 Intermediate Similarity NPC2379
0.7191 Intermediate Similarity NPC284472
0.7191 Intermediate Similarity NPC263087
0.7191 Intermediate Similarity NPC106912

  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 NPC251026 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
0.7582 Intermediate Similarity NPD7838 Discovery
0.7579 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD6698 Approved
0.7204 Intermediate Similarity NPD46 Approved
0.699 Remote Similarity NPD6686 Approved
0.6726 Remote Similarity NPD7830 Approved
0.6726 Remote Similarity NPD7829 Approved
0.6696 Remote Similarity NPD7503 Approved
0.6667 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6627 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6598 Remote Similarity NPD7983 Approved
0.6569 Remote Similarity NPD5344 Discontinued
0.6559 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6648 Approved
0.6442 Remote Similarity NPD1407 Approved
0.6429 Remote Similarity NPD7641 Discontinued
0.6404 Remote Similarity NPD8516 Approved
0.6404 Remote Similarity NPD8513 Phase 3
0.6404 Remote Similarity NPD8515 Approved
0.6404 Remote Similarity NPD8444 Approved
0.6404 Remote Similarity NPD8517 Approved
0.633 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6316 Remote Similarity NPD2269 Approved
0.6296 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7642 Approved
0.6283 Remote Similarity NPD7328 Approved
0.6283 Remote Similarity NPD7327 Approved
0.6261 Remote Similarity NPD8033 Approved
0.6228 Remote Similarity NPD7516 Approved
0.6186 Remote Similarity NPD8451 Approved
0.6184 Remote Similarity NPD904 Phase 3
0.6184 Remote Similarity NPD905 Approved
0.6176 Remote Similarity NPD7839 Suspended
0.6174 Remote Similarity NPD8294 Approved
0.6174 Remote Similarity NPD8377 Approved
0.6134 Remote Similarity NPD8448 Approved
0.6121 Remote Similarity NPD8379 Approved
0.6121 Remote Similarity NPD8378 Approved
0.6121 Remote Similarity NPD8335 Approved
0.6121 Remote Similarity NPD8296 Approved
0.6121 Remote Similarity NPD8380 Approved
0.6049 Remote Similarity NPD6109 Phase 1
0.6049 Remote Similarity NPD585 Clinical (unspecified phase)
0.6049 Remote Similarity NPD9119 Approved
0.6049 Remote Similarity NPD69 Approved
0.6026 Remote Similarity NPD892 Phase 3
0.6026 Remote Similarity NPD887 Approved
0.6026 Remote Similarity NPD891 Phase 3
0.6026 Remote Similarity NPD888 Phase 3
0.6026 Remote Similarity NPD890 Clinical (unspecified phase)
0.6026 Remote Similarity NPD895 Approved
0.6026 Remote Similarity NPD894 Approved
0.6026 Remote Similarity NPD889 Approved
0.6026 Remote Similarity NPD893 Approved
0.5984 Remote Similarity NPD8390 Approved
0.5984 Remote Similarity NPD8392 Approved
0.5984 Remote Similarity NPD8391 Approved
0.5966 Remote Similarity NPD8341 Approved
0.5966 Remote Similarity NPD8342 Approved
0.5966 Remote Similarity NPD8299 Approved
0.5966 Remote Similarity NPD8340 Approved
0.5963 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5926 Remote Similarity NPD9118 Approved
0.5917 Remote Similarity NPD7507 Approved
0.5904 Remote Similarity NPD6123 Approved
0.5868 Remote Similarity NPD8074 Phase 3
0.5862 Remote Similarity NPD897 Approved
0.5862 Remote Similarity NPD898 Approved
0.5862 Remote Similarity NPD896 Approved
0.5859 Remote Similarity NPD4251 Approved
0.5859 Remote Similarity NPD4250 Approved
0.5818 Remote Similarity NPD6412 Phase 2
0.5804 Remote Similarity NPD6371 Approved
0.5802 Remote Similarity NPD7266 Discontinued
0.5789 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5784 Remote Similarity NPD7637 Suspended
0.5776 Remote Similarity NPD7505 Discontinued
0.5773 Remote Similarity NPD6110 Phase 1
0.5772 Remote Similarity NPD7319 Approved
0.5758 Remote Similarity NPD4249 Approved
0.5755 Remote Similarity NPD4225 Approved
0.5728 Remote Similarity NPD5778 Approved
0.5728 Remote Similarity NPD5779 Approved
0.5703 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5702 Remote Similarity NPD969 Suspended
0.5698 Remote Similarity NPD3197 Phase 1
0.5684 Remote Similarity NPD7329 Approved
0.5641 Remote Similarity NPD7500 Approved
0.5638 Remote Similarity NPD4756 Discovery
0.5632 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5614 Remote Similarity NPD7116 Clinical (unspecified phase)
0.561 Remote Similarity NPD2267 Suspended

  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