Structure

Physi-Chem Properties

Molecular Weight:  262.19
Volume:  306.986
LogP:  4.171
LogD:  3.805
LogS:  -3.896
# Rotatable Bonds:  8
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.401
Synthetic Accessibility Score:  3.983
Fsp3:  0.647
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.41
MDCK Permeability:  3.0973864340921864e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.506
Human Intestinal Absorption (HIA):  0.147
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.469
Plasma Protein Binding (PPB):  100.1255874633789%
Volume Distribution (VD):  1.631
Pgp-substrate:  1.788070559501648%

ADMET: Metabolism

CYP1A2-inhibitor:  0.733
CYP1A2-substrate:  0.65
CYP2C19-inhibitor:  0.905
CYP2C19-substrate:  0.632
CYP2C9-inhibitor:  0.824
CYP2C9-substrate:  0.98
CYP2D6-inhibitor:  0.048
CYP2D6-substrate:  0.227
CYP3A4-inhibitor:  0.832
CYP3A4-substrate:  0.137

ADMET: Excretion

Clearance (CL):  9.646
Half-life (T1/2):  0.799

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.552
Drug-inuced Liver Injury (DILI):  0.952
AMES Toxicity:  0.837
Rat Oral Acute Toxicity:  0.995
Maximum Recommended Daily Dose:  1.0
Skin Sensitization:  0.952
Carcinogencity:  0.233
Eye Corrosion:  0.956
Eye Irritation:  0.979
Respiratory Toxicity:  0.99

Download Data

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

  Natural Product: NPC72699

Natural Product ID:  NPC72699
Common Name*:   Oplopandiol
IUPAC Name:   (Z,3S,8S)-heptadec-9-en-4,6-diyne-3,8-diol
Synonyms:   Oplopandiol
Standard InCHIKey:  CGMZKZLQZWZKJO-RCQSYPNMSA-N
Standard InCHI:  InChI=1S/C17H26O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h10,14,16-19H,3-9H2,1-2H3/b14-10-/t16-,17-/m0/s1
SMILES:  CCCCCCC/C=C[C@@H](C#CC#C[C@H](CC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463219
PubChem CID:   6474833
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. leaf n.a. PMID[18409045]
NPO29141 Panax ginseng Species Araliaceae Eukaryota flower buds n.a. n.a. PMID[19926279]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[20218656]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota stems n.a. n.a. PMID[20387902]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. root n.a. PMID[2092947]
NPO29141 Panax ginseng Species Araliaceae Eukaryota berry n.a. n.a. PMID[21216145]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota Tubers n.a. n.a. PMID[23356207]
NPO29141 Panax ginseng Species Araliaceae Eukaryota leaves n.a. n.a. PMID[24290061]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[24968750]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[25152999]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. stem n.a. PMID[27914541]
NPO29141 Panax ginseng Species Araliaceae Eukaryota Flower Buds n.a. n.a. PMID[28345906]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[9392889]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24374 Brunsvigia orientalis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23922 Helichrysum oxyphyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25131 Parmelia weberi Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25663 Piscidia piscipula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23679 Streptomyces roseiscleroticus Species Streptomycetaceae 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
NPT1785 Individual Protein Serotonin 7 (5-HT7) receptor Homo sapiens Inhibition = 5.0 % PMID[573526]
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 40000.0 nM PMID[573528]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 2990.0 nM PMID[573528]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 2720.0 nM PMID[573528]
NPT19 Organism Escherichia coli Escherichia coli MIC = 6.25 ug.mL-1 PMID[573525]
NPT19 Organism Escherichia coli Escherichia coli MIC > 50.0 ug.mL-1 PMID[573525]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 50.0 ug.mL-1 PMID[573525]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 6.25 ug.mL-1 PMID[573525]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 6.25 ug.mL-1 PMID[573525]
NPT20 Organism Candida albicans Candida albicans MIC = 12.5 ug.mL-1 PMID[573525]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 61.5 ug.mL-1 PMID[573527]
NPT2 Others Unspecified Selectivity Index = 6.2 n.a. PMID[573527]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 2.5 n.a. PMID[573529]

☑ 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 NPC72699 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
0.9787 High Similarity NPC151782
0.9783 High Similarity NPC31194
0.9783 High Similarity NPC153538
0.9783 High Similarity NPC248884
0.9783 High Similarity NPC85079
0.9375 High Similarity NPC93639
0.9362 High Similarity NPC471280
0.9362 High Similarity NPC471275
0.9362 High Similarity NPC471276
0.9362 High Similarity NPC125122
0.9348 High Similarity NPC124183
0.9348 High Similarity NPC35141
0.9348 High Similarity NPC55063
0.9348 High Similarity NPC19834
0.92 High Similarity NPC256209
0.92 High Similarity NPC49059
0.9167 High Similarity NPC477727
0.9167 High Similarity NPC249670
0.9167 High Similarity NPC471281
0.9167 High Similarity NPC474642
0.9167 High Similarity NPC473913
0.9167 High Similarity NPC199286
0.913 High Similarity NPC269074
0.898 High Similarity NPC224148
0.898 High Similarity NPC471959
0.898 High Similarity NPC89824
0.898 High Similarity NPC76198
0.898 High Similarity NPC197272
0.898 High Similarity NPC329608
0.898 High Similarity NPC71053
0.898 High Similarity NPC170776
0.898 High Similarity NPC165447
0.898 High Similarity NPC294278
0.898 High Similarity NPC477723
0.898 High Similarity NPC59408
0.898 High Similarity NPC475477
0.898 High Similarity NPC9273
0.898 High Similarity NPC55383
0.898 High Similarity NPC256656
0.8913 High Similarity NPC101616
0.8824 High Similarity NPC110732
0.8824 High Similarity NPC473532
0.88 High Similarity NPC142092
0.8776 High Similarity NPC291437
0.8776 High Similarity NPC328784
0.8654 High Similarity NPC473721
0.8654 High Similarity NPC473725
0.8654 High Similarity NPC477725
0.8654 High Similarity NPC477726
0.8654 High Similarity NPC473896
0.8654 High Similarity NPC473735
0.8654 High Similarity NPC475353
0.8654 High Similarity NPC473910
0.86 High Similarity NPC129263
0.8571 High Similarity NPC302310
0.8542 High Similarity NPC180575
0.8511 High Similarity NPC108195
0.8491 Intermediate Similarity NPC470968
0.8491 Intermediate Similarity NPC470967
0.8491 Intermediate Similarity NPC471960
0.8491 Intermediate Similarity NPC477661
0.8491 Intermediate Similarity NPC470969
0.8491 Intermediate Similarity NPC161838
0.8491 Intermediate Similarity NPC470966
0.8491 Intermediate Similarity NPC473847
0.8491 Intermediate Similarity NPC475384
0.8478 Intermediate Similarity NPC304151
0.8462 Intermediate Similarity NPC48058
0.8333 Intermediate Similarity NPC193975
0.8333 Intermediate Similarity NPC470970
0.8302 Intermediate Similarity NPC474644
0.8302 Intermediate Similarity NPC474513
0.8302 Intermediate Similarity NPC471239
0.8302 Intermediate Similarity NPC146551
0.8302 Intermediate Similarity NPC470963
0.8269 Intermediate Similarity NPC34577
0.8235 Intermediate Similarity NPC474495
0.8235 Intermediate Similarity NPC473672
0.8163 Intermediate Similarity NPC157096
0.8148 Intermediate Similarity NPC311648
0.8148 Intermediate Similarity NPC470964
0.8148 Intermediate Similarity NPC474643
0.8148 Intermediate Similarity NPC473865
0.8085 Intermediate Similarity NPC149668
0.8 Intermediate Similarity NPC212730
0.8 Intermediate Similarity NPC265551
0.8 Intermediate Similarity NPC48968
0.8 Intermediate Similarity NPC594
0.7963 Intermediate Similarity NPC152668
0.7959 Intermediate Similarity NPC276825
0.7931 Intermediate Similarity NPC29697
0.7925 Intermediate Similarity NPC187361
0.7925 Intermediate Similarity NPC61177
0.7925 Intermediate Similarity NPC26102
0.7925 Intermediate Similarity NPC477724
0.7895 Intermediate Similarity NPC471278
0.7826 Intermediate Similarity NPC15934
0.7759 Intermediate Similarity NPC475984
0.7759 Intermediate Similarity NPC66460
0.7759 Intermediate Similarity NPC271282
0.7759 Intermediate Similarity NPC325929
0.7719 Intermediate Similarity NPC473652
0.7708 Intermediate Similarity NPC206906
0.7692 Intermediate Similarity NPC473768
0.7679 Intermediate Similarity NPC44542
0.7679 Intermediate Similarity NPC472445
0.766 Intermediate Similarity NPC329762
0.766 Intermediate Similarity NPC103236
0.766 Intermediate Similarity NPC27444
0.7627 Intermediate Similarity NPC470965
0.7593 Intermediate Similarity NPC474496
0.7593 Intermediate Similarity NPC284224
0.7551 Intermediate Similarity NPC116934
0.7547 Intermediate Similarity NPC29234
0.75 Intermediate Similarity NPC470320
0.75 Intermediate Similarity NPC475153
0.75 Intermediate Similarity NPC226592
0.7458 Intermediate Similarity NPC168407
0.7414 Intermediate Similarity NPC222852
0.7407 Intermediate Similarity NPC473705
0.7407 Intermediate Similarity NPC35756
0.7391 Intermediate Similarity NPC216416
0.7358 Intermediate Similarity NPC474460
0.7358 Intermediate Similarity NPC475071
0.7347 Intermediate Similarity NPC249801
0.7347 Intermediate Similarity NPC46248
0.7321 Intermediate Similarity NPC317899
0.7273 Intermediate Similarity NPC217188
0.7255 Intermediate Similarity NPC76976
0.7255 Intermediate Similarity NPC140501
0.7255 Intermediate Similarity NPC160628
0.7241 Intermediate Similarity NPC181872
0.72 Intermediate Similarity NPC252978
0.7174 Intermediate Similarity NPC213767
0.717 Intermediate Similarity NPC267110
0.7143 Intermediate Similarity NPC269823
0.7119 Intermediate Similarity NPC122239
0.7119 Intermediate Similarity NPC473866
0.7083 Intermediate Similarity NPC182840
0.7083 Intermediate Similarity NPC103213
0.7083 Intermediate Similarity NPC255042
0.7083 Intermediate Similarity NPC29091
0.7083 Intermediate Similarity NPC306850
0.7069 Intermediate Similarity NPC121034
0.7069 Intermediate Similarity NPC471279
0.7069 Intermediate Similarity NPC474577
0.7069 Intermediate Similarity NPC471277
0.7059 Intermediate Similarity NPC138935
0.7049 Intermediate Similarity NPC55068
0.7037 Intermediate Similarity NPC473487
0.7037 Intermediate Similarity NPC20934
0.7037 Intermediate Similarity NPC288381
0.7037 Intermediate Similarity NPC182102
0.7037 Intermediate Similarity NPC26960
0.7018 Intermediate Similarity NPC227135
0.7018 Intermediate Similarity NPC329686
0.7 Intermediate Similarity NPC213538
0.7 Intermediate Similarity NPC256766
0.7 Intermediate Similarity NPC327112
0.6957 Remote Similarity NPC58957
0.6949 Remote Similarity NPC226848
0.6923 Remote Similarity NPC474362
0.6923 Remote Similarity NPC474202
0.6909 Remote Similarity NPC244038
0.6897 Remote Similarity NPC472808
0.6897 Remote Similarity NPC324224
0.6885 Remote Similarity NPC477829
0.6875 Remote Similarity NPC34873
0.6875 Remote Similarity NPC40434
0.6875 Remote Similarity NPC473752
0.6842 Remote Similarity NPC300121
0.6842 Remote Similarity NPC269615
0.6842 Remote Similarity NPC189677
0.6833 Remote Similarity NPC474267
0.6833 Remote Similarity NPC475931
0.6825 Remote Similarity NPC136164
0.6825 Remote Similarity NPC255863
0.6825 Remote Similarity NPC308844
0.6825 Remote Similarity NPC245947
0.6809 Remote Similarity NPC79544
0.6739 Remote Similarity NPC250734
0.6739 Remote Similarity NPC81989
0.6731 Remote Similarity NPC474413
0.6731 Remote Similarity NPC145755
0.6731 Remote Similarity NPC473539
0.6731 Remote Similarity NPC267514
0.6724 Remote Similarity NPC232247
0.6724 Remote Similarity NPC251666
0.6721 Remote Similarity NPC471081
0.6721 Remote Similarity NPC130807
0.6667 Remote Similarity NPC469373
0.6667 Remote Similarity NPC174396
0.6667 Remote Similarity NPC475723
0.6667 Remote Similarity NPC155025
0.6667 Remote Similarity NPC300593
0.6667 Remote Similarity NPC31121
0.6615 Remote Similarity NPC99619
0.6615 Remote Similarity NPC26500
0.6613 Remote Similarity NPC26810
0.6613 Remote Similarity NPC113293

  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 NPC72699 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
0.7255 Intermediate Similarity NPD4265 Approved
0.7049 Intermediate Similarity NPD3210 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.661 Remote Similarity NPD4219 Approved
0.6393 Remote Similarity NPD585 Clinical (unspecified phase)
0.6349 Remote Similarity NPD368 Approved
0.6324 Remote Similarity NPD3212 Clinical (unspecified phase)
0.6167 Remote Similarity NPD342 Phase 1
0.6167 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6154 Remote Similarity NPD3197 Phase 1
0.6119 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6 Remote Similarity NPD39 Approved
0.5974 Remote Similarity NPD5331 Approved
0.5974 Remote Similarity NPD5332 Approved
0.5972 Remote Similarity NPD8264 Approved
0.5965 Remote Similarity NPD4220 Pre-registration
0.5915 Remote Similarity NPD4732 Discontinued
0.5833 Remote Similarity NPD3172 Approved
0.5738 Remote Similarity NPD3196 Approved
0.5738 Remote Similarity NPD3195 Phase 2
0.5738 Remote Similarity NPD3194 Approved
0.5738 Remote Similarity NPD4266 Approved
0.5733 Remote Similarity NPD4268 Approved
0.5733 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5733 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5733 Remote Similarity NPD4271 Approved
0.5714 Remote Similarity NPD4222 Approved
0.5714 Remote Similarity NPD6898 Phase 1
0.569 Remote Similarity NPD3173 Approved
0.5636 Remote Similarity NPD5326 Phase 3
0.5625 Remote Similarity NPD6109 Phase 1
0.5606 Remote Similarity NPD4191 Approved
0.5606 Remote Similarity NPD4193 Approved
0.5606 Remote Similarity NPD4192 Approved
0.5606 Remote Similarity NPD4194 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