Structure

Physi-Chem Properties

Molecular Weight:  226.08
Volume:  211.821
LogP:  0.608
LogD:  1.028
LogS:  -1.397
# Rotatable Bonds:  2
TPSA:  53.99
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.619
Synthetic Accessibility Score:  5.881
Fsp3:  0.727
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:  -4.697
MDCK Permeability:  5.20373614563141e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  23.552108764648438%
Volume Distribution (VD):  1.598
Pgp-substrate:  72.9225082397461%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.084
CYP2C19-substrate:  0.888
CYP2C9-inhibitor:  0.03
CYP2C9-substrate:  0.067
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.352
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.576

ADMET: Excretion

Clearance (CL):  13.282
Half-life (T1/2):  0.571

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.624
Drug-inuced Liver Injury (DILI):  0.664
AMES Toxicity:  0.98
Rat Oral Acute Toxicity:  0.092
Maximum Recommended Daily Dose:  0.851
Skin Sensitization:  0.132
Carcinogencity:  0.968
Eye Corrosion:  0.004
Eye Irritation:  0.281
Respiratory Toxicity:  0.93

Download Data

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

  Natural Product: NPC323472

Natural Product ID:  NPC323472
Common Name*:   QGBCGMGBGAHJIT-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QGBCGMGBGAHJIT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H14O5/c1-5-9-6-3-8(15-5)16-11(9)14-4-7(6)10(12)13-2/h4-6,8-9,11H,3H2,1-2H3
SMILES:  CC1C2C3CC(O1)OC2OC=C3C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1982244
PubChem CID:   427877
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000368] Dioxanes
        • [CHEMONTID:0001314] 1,3-dioxanes

*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
NPO12588 Cornus officinalis Species Cornaceae Eukaryota Fruits n.a. n.a. PMID[29140705]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31091 Comus officinalis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12588 Cornus officinalis Species Cornaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[454308]

☑ 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 NPC323472 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
0.869 High Similarity NPC120021
0.869 High Similarity NPC216826
0.869 High Similarity NPC65665
0.869 High Similarity NPC231710
0.869 High Similarity NPC270908
0.869 High Similarity NPC470573
0.8161 Intermediate Similarity NPC472124
0.8161 Intermediate Similarity NPC472125
0.8161 Intermediate Similarity NPC472126
0.8046 Intermediate Similarity NPC307699
0.7907 Intermediate Similarity NPC74139
0.7841 Intermediate Similarity NPC117596
0.7816 Intermediate Similarity NPC473151
0.7692 Intermediate Similarity NPC101051
0.7667 Intermediate Similarity NPC61201
0.7579 Intermediate Similarity NPC222062
0.75 Intermediate Similarity NPC284929
0.75 Intermediate Similarity NPC469543
0.75 Intermediate Similarity NPC267869
0.75 Intermediate Similarity NPC118761
0.75 Intermediate Similarity NPC197541
0.75 Intermediate Similarity NPC234304
0.7444 Intermediate Similarity NPC303451
0.7444 Intermediate Similarity NPC6414
0.7396 Intermediate Similarity NPC4899
0.7396 Intermediate Similarity NPC195510
0.7396 Intermediate Similarity NPC177013
0.7396 Intermediate Similarity NPC474730
0.7396 Intermediate Similarity NPC35185
0.7396 Intermediate Similarity NPC13171
0.7368 Intermediate Similarity NPC22149
0.7368 Intermediate Similarity NPC255677
0.7368 Intermediate Similarity NPC306344
0.7347 Intermediate Similarity NPC41681
0.732 Intermediate Similarity NPC37240
0.7292 Intermediate Similarity NPC28304
0.7292 Intermediate Similarity NPC298255
0.7234 Intermediate Similarity NPC161293
0.7216 Intermediate Similarity NPC261117
0.7216 Intermediate Similarity NPC106668
0.7216 Intermediate Similarity NPC310804
0.7172 Intermediate Similarity NPC170432
0.7143 Intermediate Similarity NPC475928
0.7143 Intermediate Similarity NPC27687
0.7128 Intermediate Similarity NPC170204
0.7113 Intermediate Similarity NPC287539
0.7113 Intermediate Similarity NPC3488
0.7111 Intermediate Similarity NPC142583
0.71 Intermediate Similarity NPC148270
0.71 Intermediate Similarity NPC197813
0.71 Intermediate Similarity NPC254538
0.71 Intermediate Similarity NPC80338
0.71 Intermediate Similarity NPC474285
0.7071 Intermediate Similarity NPC86095
0.7053 Intermediate Similarity NPC241911
0.7053 Intermediate Similarity NPC148872
0.7041 Intermediate Similarity NPC250545
0.7021 Intermediate Similarity NPC475927
0.7021 Intermediate Similarity NPC475832
0.69 Remote Similarity NPC305157
0.69 Remote Similarity NPC307846
0.6897 Remote Similarity NPC475946
0.6893 Remote Similarity NPC193741
0.6854 Remote Similarity NPC211455
0.6854 Remote Similarity NPC188717
0.6842 Remote Similarity NPC63897
0.6832 Remote Similarity NPC127235
0.6818 Remote Similarity NPC47635
0.6809 Remote Similarity NPC470379
0.6809 Remote Similarity NPC470373
0.6771 Remote Similarity NPC167893
0.6762 Remote Similarity NPC475924
0.6762 Remote Similarity NPC475851
0.6706 Remote Similarity NPC471491
0.6699 Remote Similarity NPC110701
0.6667 Remote Similarity NPC471057
0.6667 Remote Similarity NPC71589
0.6667 Remote Similarity NPC471058
0.6667 Remote Similarity NPC469402
0.6632 Remote Similarity NPC477749
0.6632 Remote Similarity NPC66504
0.663 Remote Similarity NPC471480
0.6593 Remote Similarity NPC266718
0.6591 Remote Similarity NPC321728
0.6566 Remote Similarity NPC472015
0.6566 Remote Similarity NPC40182
0.6566 Remote Similarity NPC473307
0.6566 Remote Similarity NPC198422
0.6556 Remote Similarity NPC10080
0.6556 Remote Similarity NPC123908
0.6535 Remote Similarity NPC80144
0.6535 Remote Similarity NPC304163
0.6531 Remote Similarity NPC306041
0.6526 Remote Similarity NPC80875
0.6517 Remote Similarity NPC474981
0.6495 Remote Similarity NPC25701
0.6495 Remote Similarity NPC274588
0.6495 Remote Similarity NPC294293
0.6495 Remote Similarity NPC2003
0.6465 Remote Similarity NPC153559
0.6465 Remote Similarity NPC472290
0.6436 Remote Similarity NPC67296
0.6429 Remote Similarity NPC291709
0.6429 Remote Similarity NPC6765
0.6429 Remote Similarity NPC93869
0.6429 Remote Similarity NPC241407
0.6421 Remote Similarity NPC477748
0.6413 Remote Similarity NPC475035
0.6413 Remote Similarity NPC138647
0.6413 Remote Similarity NPC470238
0.6408 Remote Similarity NPC476763
0.6408 Remote Similarity NPC476764
0.6408 Remote Similarity NPC244247
0.64 Remote Similarity NPC249171
0.64 Remote Similarity NPC124181
0.64 Remote Similarity NPC49833
0.64 Remote Similarity NPC279561
0.6392 Remote Similarity NPC320552
0.6381 Remote Similarity NPC473807
0.6381 Remote Similarity NPC392
0.6381 Remote Similarity NPC177524
0.6381 Remote Similarity NPC219900
0.6381 Remote Similarity NPC475960
0.6373 Remote Similarity NPC471599
0.6364 Remote Similarity NPC284063
0.6364 Remote Similarity NPC170527
0.6364 Remote Similarity NPC10572
0.6364 Remote Similarity NPC143446
0.6364 Remote Similarity NPC317573
0.6364 Remote Similarity NPC54731
0.6354 Remote Similarity NPC202886
0.6354 Remote Similarity NPC327253
0.6346 Remote Similarity NPC476761
0.6346 Remote Similarity NPC476762
0.6346 Remote Similarity NPC469401
0.6346 Remote Similarity NPC476760
0.6344 Remote Similarity NPC470124
0.6344 Remote Similarity NPC477747
0.6344 Remote Similarity NPC477746
0.6344 Remote Similarity NPC474547
0.6333 Remote Similarity NPC474510
0.6327 Remote Similarity NPC41649
0.6327 Remote Similarity NPC477722
0.6327 Remote Similarity NPC238264
0.6327 Remote Similarity NPC477345
0.6327 Remote Similarity NPC474841
0.6327 Remote Similarity NPC471446
0.6327 Remote Similarity NPC473434
0.6327 Remote Similarity NPC477348
0.6321 Remote Similarity NPC112457
0.6321 Remote Similarity NPC471250
0.6316 Remote Similarity NPC233997
0.6311 Remote Similarity NPC473148
0.6311 Remote Similarity NPC197736
0.6304 Remote Similarity NPC257358
0.6304 Remote Similarity NPC170377
0.6304 Remote Similarity NPC474472
0.63 Remote Similarity NPC304445
0.63 Remote Similarity NPC86843
0.63 Remote Similarity NPC236580
0.6289 Remote Similarity NPC9447
0.6289 Remote Similarity NPC476934
0.6277 Remote Similarity NPC47220
0.6277 Remote Similarity NPC470242
0.6277 Remote Similarity NPC186332
0.6277 Remote Similarity NPC162071
0.6275 Remote Similarity NPC219038
0.6262 Remote Similarity NPC83005
0.625 Remote Similarity NPC474917
0.625 Remote Similarity NPC469869
0.6238 Remote Similarity NPC37866
0.6238 Remote Similarity NPC151093
0.6238 Remote Similarity NPC90819
0.6237 Remote Similarity NPC38569
0.6237 Remote Similarity NPC474780
0.6237 Remote Similarity NPC163615
0.6226 Remote Similarity NPC232133
0.6224 Remote Similarity NPC472196
0.6224 Remote Similarity NPC320089
0.6224 Remote Similarity NPC472195
0.6224 Remote Similarity NPC474835
0.6224 Remote Similarity NPC163902
0.6224 Remote Similarity NPC238090
0.6214 Remote Similarity NPC201191
0.6211 Remote Similarity NPC316138
0.6211 Remote Similarity NPC175293
0.6211 Remote Similarity NPC5130
0.6211 Remote Similarity NPC313658
0.6211 Remote Similarity NPC475037
0.6211 Remote Similarity NPC118601
0.6211 Remote Similarity NPC190753
0.6207 Remote Similarity NPC48641
0.6207 Remote Similarity NPC474758
0.6204 Remote Similarity NPC471251
0.6204 Remote Similarity NPC270586
0.62 Remote Similarity NPC475540
0.62 Remote Similarity NPC475241
0.62 Remote Similarity NPC473605
0.62 Remote Similarity NPC311166
0.62 Remote Similarity NPC476066

  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 NPC323472 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
0.6381 Remote Similarity NPD6686 Approved
0.617 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6 Remote Similarity NPD8513 Phase 3
0.5946 Remote Similarity NPD8133 Approved
0.5922 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5862 Remote Similarity NPD8517 Approved
0.5862 Remote Similarity NPD8515 Approved
0.5862 Remote Similarity NPD8516 Approved
0.5859 Remote Similarity NPD6698 Approved
0.5859 Remote Similarity NPD46 Approved
0.5856 Remote Similarity NPD6053 Discontinued
0.5766 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5758 Remote Similarity NPD1695 Approved
0.5745 Remote Similarity NPD1780 Approved
0.5745 Remote Similarity NPD1779 Approved
0.5684 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5667 Remote Similarity NPD7507 Approved
0.563 Remote Similarity NPD7830 Approved
0.563 Remote Similarity NPD7829 Approved
0.56 Remote Similarity NPD5764 Clinical (unspecified phase)
0.56 Remote Similarity NPD6101 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