Structure

Physi-Chem Properties

Molecular Weight:  208.07
Volume:  212.234
LogP:  0.521
LogD:  1.015
LogS:  -1.642
# Rotatable Bonds:  4
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.658
Synthetic Accessibility Score:  3.765
Fsp3:  0.182
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.543
MDCK Permeability:  1.5297009667847306e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.058
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.404
Plasma Protein Binding (PPB):  62.75688934326172%
Volume Distribution (VD):  0.336
Pgp-substrate:  32.552345275878906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.727
CYP1A2-substrate:  0.07
CYP2C19-inhibitor:  0.066
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.936
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.442
CYP3A4-inhibitor:  0.035
CYP3A4-substrate:  0.154

ADMET: Excretion

Clearance (CL):  3.61
Half-life (T1/2):  0.901

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.984
Drug-inuced Liver Injury (DILI):  0.97
AMES Toxicity:  0.975
Rat Oral Acute Toxicity:  0.58
Maximum Recommended Daily Dose:  0.866
Skin Sensitization:  0.951
Carcinogencity:  0.881
Eye Corrosion:  0.419
Eye Irritation:  0.951
Respiratory Toxicity:  0.932

Download Data

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

  Natural Product: NPC98519

Natural Product ID:  NPC98519
Common Name*:   Lissoclinolide
IUPAC Name:   (5Z)-5-[(E)-4-hydroxybut-2-enylidene]-3-[(E)-3-hydroxyprop-1-enyl]furan-2-one
Synonyms:   Lissoclinolide
Standard InCHIKey:  ZYNGLDJNLYFSIV-CZFMBXACSA-N
Standard InCHI:  InChI=1S/C11H12O4/c12-6-2-1-5-10-8-9(4-3-7-13)11(14)15-10/h1-5,8,12-13H,6-7H2/b2-1+,4-3+,10-5-
SMILES:  OC/C=C/C=C1/C=C(C(=O)O1)/C=C/CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465684
PubChem CID:   5472800
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
NPO4712 Lissoclinum patella Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[1593285]
NPO21754 Diplosoma virens Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[18463568]
NPO4712 Lissoclinum patella Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[2095371]
NPO4712 Lissoclinum patella Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[2809606]
NPO4712 Lissoclinum patella Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[7623037]
NPO4712 Lissoclinum patella Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[9868162]
NPO23150 Anemone obtusiloba Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20599 Croton glabellus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23150 Anemone obtusiloba Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4712 Lissoclinum patella Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21754 Diplosoma virens Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20267 Pternistria bispina n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21699 Delphinium majus Species Ranunculaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 27925.44 nM PMID[573432]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 21330.45 nM PMID[573432]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 24154.61 nM PMID[573432]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 18450.15 nM PMID[573432]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 16519.62 nM PMID[573432]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 29308.93 nM PMID[573432]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 24099.05 nM PMID[573432]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 20989.4 nM PMID[573432]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 22080.05 nM PMID[573432]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 13835.66 nM PMID[573432]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 31188.9 nM PMID[573432]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 50582.47 nM PMID[573432]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 24210.29 nM PMID[573432]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 33342.64 nM PMID[573432]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 40831.94 nM PMID[573432]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 19230.92 nM PMID[573432]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 20044.72 nM PMID[573432]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 21281.39 nM PMID[573432]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 23496.33 nM PMID[573432]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 34914.03 nM PMID[573432]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 19098.53 nM PMID[573432]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 18197.01 nM PMID[573432]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 10327.61 nM PMID[573432]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 36897.76 nM PMID[573432]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 20183.66 nM PMID[573432]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 31188.9 nM PMID[573432]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 16443.72 nM PMID[573432]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 45498.81 nM PMID[573432]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 35563.13 nM PMID[573432]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 19998.62 nM PMID[573432]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 19319.68 nM PMID[573432]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 36391.5 nM PMID[573432]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[573432]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 14028.14 nM PMID[573432]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 12331.05 nM PMID[573432]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 24490.63 nM PMID[573432]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 15346.17 nM PMID[573432]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 36307.81 nM PMID[573432]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 14288.94 nM PMID[573432]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 61235.04 nM PMID[573432]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 32062.69 nM PMID[573432]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 20701.41 nM PMID[573432]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 18923.44 nM PMID[573432]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 35727.28 nM PMID[573432]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 14521.12 nM PMID[573432]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 16032.45 nM PMID[573432]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 38994.2 nM PMID[573432]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 12473.84 nM PMID[573432]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 22855.99 nM PMID[573432]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 36475.39 nM PMID[573432]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 22961.49 nM PMID[573432]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 24378.11 nM PMID[573432]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 2228.44 nM PMID[573432]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 18967.06 nM PMID[573432]

☑ 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 NPC98519 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
0.9649 High Similarity NPC130953
0.9298 High Similarity NPC189700
0.8689 High Similarity NPC473737
0.8305 Intermediate Similarity NPC51846
0.8095 Intermediate Similarity NPC2328
0.8 Intermediate Similarity NPC150717
0.7969 Intermediate Similarity NPC471611
0.7966 Intermediate Similarity NPC218486
0.7857 Intermediate Similarity NPC478194
0.7857 Intermediate Similarity NPC478191
0.7857 Intermediate Similarity NPC478193
0.7857 Intermediate Similarity NPC478195
0.7857 Intermediate Similarity NPC478196
0.7857 Intermediate Similarity NPC478192
0.7794 Intermediate Similarity NPC59558
0.7778 Intermediate Similarity NPC309408
0.7761 Intermediate Similarity NPC287705
0.7727 Intermediate Similarity NPC37382
0.7705 Intermediate Similarity NPC221763
0.7627 Intermediate Similarity NPC191643
0.7619 Intermediate Similarity NPC133600
0.7586 Intermediate Similarity NPC15789
0.7581 Intermediate Similarity NPC135863
0.7581 Intermediate Similarity NPC129150
0.7576 Intermediate Similarity NPC273600
0.7538 Intermediate Similarity NPC179087
0.7538 Intermediate Similarity NPC475073
0.7538 Intermediate Similarity NPC44343
0.7538 Intermediate Similarity NPC210303
0.75 Intermediate Similarity NPC474823
0.7465 Intermediate Similarity NPC470686
0.746 Intermediate Similarity NPC254095
0.746 Intermediate Similarity NPC223679
0.7419 Intermediate Similarity NPC230296
0.7391 Intermediate Similarity NPC475004
0.7361 Intermediate Similarity NPC161038
0.7353 Intermediate Similarity NPC132286
0.7344 Intermediate Similarity NPC82465
0.7313 Intermediate Similarity NPC476589
0.7313 Intermediate Similarity NPC471566
0.7313 Intermediate Similarity NPC282760
0.7313 Intermediate Similarity NPC470123
0.7313 Intermediate Similarity NPC471565
0.7302 Intermediate Similarity NPC293437
0.7302 Intermediate Similarity NPC294938
0.7302 Intermediate Similarity NPC249850
0.7288 Intermediate Similarity NPC221467
0.7273 Intermediate Similarity NPC68110
0.726 Intermediate Similarity NPC470705
0.7258 Intermediate Similarity NPC173157
0.7258 Intermediate Similarity NPC478117
0.7246 Intermediate Similarity NPC238223
0.7206 Intermediate Similarity NPC475555
0.7206 Intermediate Similarity NPC146811
0.7206 Intermediate Similarity NPC475675
0.7188 Intermediate Similarity NPC21946
0.7183 Intermediate Similarity NPC316185
0.7167 Intermediate Similarity NPC43053
0.7164 Intermediate Similarity NPC475618
0.7162 Intermediate Similarity NPC275530
0.7119 Intermediate Similarity NPC234084
0.7119 Intermediate Similarity NPC126184
0.7101 Intermediate Similarity NPC225272
0.7097 Intermediate Similarity NPC478120
0.7077 Intermediate Similarity NPC302564
0.7077 Intermediate Similarity NPC97570
0.7059 Intermediate Similarity NPC7940
0.7059 Intermediate Similarity NPC471556
0.7059 Intermediate Similarity NPC182794
0.7059 Intermediate Similarity NPC133904
0.7015 Intermediate Similarity NPC132243
0.7 Intermediate Similarity NPC477117
0.7 Intermediate Similarity NPC236338
0.7 Intermediate Similarity NPC63873
0.6986 Remote Similarity NPC315843
0.6957 Remote Similarity NPC276299
0.6957 Remote Similarity NPC470033
0.6949 Remote Similarity NPC90490
0.6949 Remote Similarity NPC128520
0.6944 Remote Similarity NPC293114
0.6944 Remote Similarity NPC178575
0.6923 Remote Similarity NPC474084
0.6912 Remote Similarity NPC470808
0.6901 Remote Similarity NPC470693
0.6866 Remote Similarity NPC151648
0.6866 Remote Similarity NPC26810
0.6866 Remote Similarity NPC15193
0.6857 Remote Similarity NPC122627
0.6849 Remote Similarity NPC316851
0.6849 Remote Similarity NPC284006
0.6833 Remote Similarity NPC82446
0.6825 Remote Similarity NPC151761
0.6825 Remote Similarity NPC159535
0.6818 Remote Similarity NPC286189
0.6812 Remote Similarity NPC131174
0.6812 Remote Similarity NPC19769
0.6812 Remote Similarity NPC96414
0.6812 Remote Similarity NPC220766
0.6806 Remote Similarity NPC202011
0.6806 Remote Similarity NPC476037
0.68 Remote Similarity NPC127118
0.68 Remote Similarity NPC209113
0.6769 Remote Similarity NPC474825
0.6765 Remote Similarity NPC474723
0.6765 Remote Similarity NPC474729
0.6757 Remote Similarity NPC107654
0.6757 Remote Similarity NPC114727
0.6757 Remote Similarity NPC476590
0.6721 Remote Similarity NPC275316
0.6714 Remote Similarity NPC201356
0.6714 Remote Similarity NPC248125
0.6714 Remote Similarity NPC191233
0.6714 Remote Similarity NPC315115
0.6711 Remote Similarity NPC315394
0.6667 Remote Similarity NPC151481
0.6667 Remote Similarity NPC315552
0.6667 Remote Similarity NPC475982
0.6667 Remote Similarity NPC474424
0.6667 Remote Similarity NPC327103
0.6667 Remote Similarity NPC41409
0.6667 Remote Similarity NPC260396
0.6623 Remote Similarity NPC473471
0.6622 Remote Similarity NPC329890
0.662 Remote Similarity NPC203335
0.6618 Remote Similarity NPC55376
0.6615 Remote Similarity NPC86948
0.6615 Remote Similarity NPC324224
0.6615 Remote Similarity NPC245002
0.6615 Remote Similarity NPC472808
0.6579 Remote Similarity NPC203277
0.6579 Remote Similarity NPC301207
0.6575 Remote Similarity NPC315597
0.6575 Remote Similarity NPC476012
0.6575 Remote Similarity NPC315285
0.6543 Remote Similarity NPC475706
0.6528 Remote Similarity NPC313444
0.65 Remote Similarity NPC474028
0.65 Remote Similarity NPC87137
0.65 Remote Similarity NPC474439
0.6494 Remote Similarity NPC125365
0.6494 Remote Similarity NPC473825
0.6494 Remote Similarity NPC68156
0.6494 Remote Similarity NPC474818
0.6494 Remote Similarity NPC51809
0.6494 Remote Similarity NPC49302
0.6494 Remote Similarity NPC176329
0.6471 Remote Similarity NPC429928
0.6471 Remote Similarity NPC476585
0.6471 Remote Similarity NPC79756
0.6438 Remote Similarity NPC236208
0.6429 Remote Similarity NPC90463
0.6429 Remote Similarity NPC260343
0.6429 Remote Similarity NPC475739
0.6429 Remote Similarity NPC147824
0.642 Remote Similarity NPC475714
0.6418 Remote Similarity NPC187770
0.641 Remote Similarity NPC279532
0.641 Remote Similarity NPC221095
0.641 Remote Similarity NPC279214
0.64 Remote Similarity NPC326126
0.64 Remote Similarity NPC12815
0.64 Remote Similarity NPC215745
0.64 Remote Similarity NPC329914
0.64 Remote Similarity NPC287878
0.64 Remote Similarity NPC238948
0.6386 Remote Similarity NPC211892
0.6379 Remote Similarity NPC57923
0.6377 Remote Similarity NPC263732
0.6364 Remote Similarity NPC238554
0.6364 Remote Similarity NPC68819
0.6364 Remote Similarity NPC188860
0.6364 Remote Similarity NPC225022
0.6351 Remote Similarity NPC329904
0.6351 Remote Similarity NPC473361
0.6351 Remote Similarity NPC316029
0.6341 Remote Similarity NPC161670
0.6338 Remote Similarity NPC478098
0.6338 Remote Similarity NPC478099
0.6333 Remote Similarity NPC26600
0.6333 Remote Similarity NPC270706
0.6333 Remote Similarity NPC47946
0.6329 Remote Similarity NPC99651
0.6324 Remote Similarity NPC222852
0.6324 Remote Similarity NPC322186
0.6322 Remote Similarity NPC59646
0.6322 Remote Similarity NPC29798
0.6322 Remote Similarity NPC282644
0.6316 Remote Similarity NPC8270
0.6316 Remote Similarity NPC281043
0.6316 Remote Similarity NPC177030
0.631 Remote Similarity NPC45409
0.6308 Remote Similarity NPC9611
0.6308 Remote Similarity NPC474127
0.6308 Remote Similarity NPC151923
0.6301 Remote Similarity NPC218477
0.6301 Remote Similarity NPC280374
0.6296 Remote Similarity NPC16321
0.6296 Remote Similarity NPC324170
0.629 Remote Similarity NPC137419
0.629 Remote Similarity NPC135698

  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 NPC98519 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
0.6557 Remote Similarity NPD4220 Pre-registration
0.6418 Remote Similarity NPD69 Approved
0.6418 Remote Similarity NPD9119 Approved
0.6269 Remote Similarity NPD9118 Approved
0.6094 Remote Similarity NPD6927 Phase 3
0.6076 Remote Similarity NPD4756 Discovery
0.6 Remote Similarity NPD9411 Phase 1
0.5789 Remote Similarity NPD9115 Approved
0.5775 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5765 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5733 Remote Similarity NPD4247 Clinical (unspecified phase)
0.573 Remote Similarity NPD7838 Discovery
0.5714 Remote Similarity NPD5209 Approved
0.5647 Remote Similarity NPD7154 Phase 3
0.5618 Remote Similarity NPD689 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