Structure

Physi-Chem Properties

Molecular Weight:  469.91
Volume:  321.042
LogP:  3.227
LogD:  2.757
LogS:  -4.806
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.441
Synthetic Accessibility Score:  5.837
Fsp3:  0.733
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:  -4.497
MDCK Permeability:  1.6708394468878396e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.255
20% Bioavailability (F20%):  0.682
30% Bioavailability (F30%):  0.53

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.908
Plasma Protein Binding (PPB):  78.25580596923828%
Volume Distribution (VD):  1.393
Pgp-substrate:  18.44690704345703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.175
CYP1A2-substrate:  0.794
CYP2C19-inhibitor:  0.741
CYP2C19-substrate:  0.799
CYP2C9-inhibitor:  0.927
CYP2C9-substrate:  0.545
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.825
CYP3A4-substrate:  0.908

ADMET: Excretion

Clearance (CL):  2.186
Half-life (T1/2):  0.115

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.569
Drug-inuced Liver Injury (DILI):  0.068
AMES Toxicity:  0.321
Rat Oral Acute Toxicity:  0.476
Maximum Recommended Daily Dose:  0.532
Skin Sensitization:  0.344
Carcinogencity:  0.925
Eye Corrosion:  0.623
Eye Irritation:  0.218
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC311891

Natural Product ID:  NPC311891
Common Name*:   Mailiohydrin
IUPAC Name:   (3R,4S,6S,9R)-4-bromo-9-(dibromomethyl)-5,5-dimethyl-1-methylidenespiro[5.5]undec-10-ene-3,9-diol
Synonyms:   Mailiohydrin
Standard InCHIKey:  BDUUDTPDYKKJPZ-FKGLVLAHSA-N
Standard InCHI:  InChI=1S/C15H21Br3O2/c1-9-8-10(19)11(16)13(2,3)14(9)4-6-15(20,7-5-14)12(17)18/h4,6,10-12,19-20H,1,5,7-8H2,2-3H3/t10-,11-,14-,15+/m1/s1
SMILES:  C=C1C[C@H]([C@H](C(C)(C)[C@]21C=C[C@](CC2)(C(Br)Br)O)Br)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL459613
PubChem CID:   10917718
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002517] Chamigranes

*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
NPO14672 Laurencia sp. Species Rhodomelaceae Eukaryota n.a. Philippine n.a. PMID[11421745]
NPO14672 Laurencia sp. Species Rhodomelaceae Eukaryota n.a. Okinawan n.a. PMID[12088419]
NPO14672 Laurencia sp. Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[12088419]
NPO6250 Laurencia tristicha Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15974618]
NPO6250 Laurencia tristicha Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[27536968]
NPO14672 Laurencia sp. Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6250 Laurencia tristicha Species Rhodomelaceae 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
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 = 10.0 nM PMID[479239]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 10000.0 nM PMID[479239]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 >= 10000.0 nM PMID[479240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IZ = 1.0 mm PMID[479240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IZ = 2.0 mm PMID[479240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 13.0 % PMID[479240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 16.0 % PMID[479240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 22.0 % PMID[479240]

☑ 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 NPC311891 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
0.9867 High Similarity NPC113024
0.9091 High Similarity NPC215307
0.9091 High Similarity NPC274750
0.8947 High Similarity NPC35397
0.8947 High Similarity NPC474946
0.8471 Intermediate Similarity NPC188896
0.8272 Intermediate Similarity NPC31330
0.8256 Intermediate Similarity NPC131453
0.8205 Intermediate Similarity NPC476609
0.814 Intermediate Similarity NPC109900
0.8 Intermediate Similarity NPC476605
0.7922 Intermediate Similarity NPC96484
0.7912 Intermediate Similarity NPC299714
0.7912 Intermediate Similarity NPC257510
0.7901 Intermediate Similarity NPC265588
0.7901 Intermediate Similarity NPC61080
0.7826 Intermediate Similarity NPC156912
0.7821 Intermediate Similarity NPC476604
0.7753 Intermediate Similarity NPC239453
0.7753 Intermediate Similarity NPC224552
0.775 Intermediate Similarity NPC220939
0.775 Intermediate Similarity NPC265485
0.7738 Intermediate Similarity NPC15714
0.7727 Intermediate Similarity NPC174273
0.7692 Intermediate Similarity NPC471238
0.7683 Intermediate Similarity NPC476606
0.7683 Intermediate Similarity NPC253190
0.7683 Intermediate Similarity NPC476607
0.7625 Intermediate Similarity NPC477792
0.7625 Intermediate Similarity NPC471272
0.7625 Intermediate Similarity NPC23954
0.7619 Intermediate Similarity NPC476603
0.7619 Intermediate Similarity NPC83436
0.7619 Intermediate Similarity NPC476610
0.759 Intermediate Similarity NPC91594
0.7553 Intermediate Similarity NPC34732
0.7553 Intermediate Similarity NPC92231
0.7529 Intermediate Similarity NPC96362
0.75 Intermediate Similarity NPC83200
0.75 Intermediate Similarity NPC34834
0.75 Intermediate Similarity NPC167891
0.75 Intermediate Similarity NPC476314
0.75 Intermediate Similarity NPC83351
0.75 Intermediate Similarity NPC92801
0.7442 Intermediate Similarity NPC249423
0.7442 Intermediate Similarity NPC476646
0.7442 Intermediate Similarity NPC264245
0.7439 Intermediate Similarity NPC476366
0.7439 Intermediate Similarity NPC477138
0.7439 Intermediate Similarity NPC306727
0.7439 Intermediate Similarity NPC201048
0.7439 Intermediate Similarity NPC243342
0.7436 Intermediate Similarity NPC267027
0.7436 Intermediate Similarity NPC202017
0.7412 Intermediate Similarity NPC129501
0.7407 Intermediate Similarity NPC471268
0.7407 Intermediate Similarity NPC164022
0.7407 Intermediate Similarity NPC471271
0.7407 Intermediate Similarity NPC242001
0.7407 Intermediate Similarity NPC475077
0.7386 Intermediate Similarity NPC238485
0.7381 Intermediate Similarity NPC470711
0.7381 Intermediate Similarity NPC470758
0.7375 Intermediate Similarity NPC474248
0.7375 Intermediate Similarity NPC471560
0.7375 Intermediate Similarity NPC9942
0.7375 Intermediate Similarity NPC473893
0.7356 Intermediate Similarity NPC87489
0.7356 Intermediate Similarity NPC49964
0.7349 Intermediate Similarity NPC171148
0.7349 Intermediate Similarity NPC291503
0.7349 Intermediate Similarity NPC69383
0.7349 Intermediate Similarity NPC313179
0.7326 Intermediate Similarity NPC164840
0.7326 Intermediate Similarity NPC209944
0.7326 Intermediate Similarity NPC234193
0.7326 Intermediate Similarity NPC241290
0.7317 Intermediate Similarity NPC471799
0.7308 Intermediate Similarity NPC287339
0.7284 Intermediate Similarity NPC145498
0.7273 Intermediate Similarity NPC97491
0.7273 Intermediate Similarity NPC273356
0.7273 Intermediate Similarity NPC81615
0.7262 Intermediate Similarity NPC470749
0.725 Intermediate Similarity NPC208999
0.725 Intermediate Similarity NPC276616
0.7241 Intermediate Similarity NPC47761
0.7229 Intermediate Similarity NPC91858
0.7229 Intermediate Similarity NPC471797
0.7222 Intermediate Similarity NPC261266
0.7209 Intermediate Similarity NPC28862
0.7209 Intermediate Similarity NPC30986
0.7209 Intermediate Similarity NPC109546
0.7209 Intermediate Similarity NPC47982
0.7209 Intermediate Similarity NPC209430
0.7209 Intermediate Similarity NPC143182
0.7209 Intermediate Similarity NPC84694
0.7209 Intermediate Similarity NPC81306
0.7195 Intermediate Similarity NPC242992
0.7195 Intermediate Similarity NPC167706
0.7191 Intermediate Similarity NPC282598
0.7191 Intermediate Similarity NPC205845
0.7191 Intermediate Similarity NPC231310
0.7179 Intermediate Similarity NPC96793
0.7179 Intermediate Similarity NPC323424
0.7176 Intermediate Similarity NPC471798
0.7176 Intermediate Similarity NPC203403
0.7159 Intermediate Similarity NPC471408
0.7159 Intermediate Similarity NPC218616
0.7159 Intermediate Similarity NPC296701
0.7159 Intermediate Similarity NPC50964
0.7143 Intermediate Similarity NPC477923
0.7143 Intermediate Similarity NPC32832
0.7143 Intermediate Similarity NPC66566
0.7126 Intermediate Similarity NPC295131
0.7126 Intermediate Similarity NPC236707
0.7125 Intermediate Similarity NPC114651
0.7125 Intermediate Similarity NPC171225
0.7125 Intermediate Similarity NPC69649
0.7125 Intermediate Similarity NPC82337
0.7125 Intermediate Similarity NPC68703
0.7111 Intermediate Similarity NPC274448
0.7111 Intermediate Similarity NPC313115
0.7108 Intermediate Similarity NPC182717
0.7108 Intermediate Similarity NPC68443
0.7108 Intermediate Similarity NPC130665
0.7093 Intermediate Similarity NPC474216
0.7093 Intermediate Similarity NPC11908
0.7079 Intermediate Similarity NPC470384
0.7079 Intermediate Similarity NPC317458
0.7079 Intermediate Similarity NPC475789
0.7079 Intermediate Similarity NPC474634
0.7059 Intermediate Similarity NPC477925
0.7059 Intermediate Similarity NPC274079
0.7051 Intermediate Similarity NPC174956
0.7045 Intermediate Similarity NPC471270
0.7045 Intermediate Similarity NPC159148
0.7045 Intermediate Similarity NPC23852
0.7045 Intermediate Similarity NPC209620
0.7037 Intermediate Similarity NPC245795
0.7033 Intermediate Similarity NPC281316
0.7033 Intermediate Similarity NPC255143
0.7033 Intermediate Similarity NPC6391
0.7024 Intermediate Similarity NPC469533
0.7024 Intermediate Similarity NPC469593
0.7024 Intermediate Similarity NPC469534
0.7013 Intermediate Similarity NPC240506
0.7013 Intermediate Similarity NPC66020
0.7011 Intermediate Similarity NPC308038
0.7011 Intermediate Similarity NPC291379
0.7 Intermediate Similarity NPC470077
0.7 Intermediate Similarity NPC476406
0.7 Intermediate Similarity NPC326310
0.7 Intermediate Similarity NPC279434
0.7 Intermediate Similarity NPC474047
0.6989 Remote Similarity NPC115607
0.6988 Remote Similarity NPC469343
0.6988 Remote Similarity NPC110799
0.6977 Remote Similarity NPC283619
0.6977 Remote Similarity NPC198968
0.6977 Remote Similarity NPC85105
0.6977 Remote Similarity NPC155986
0.6977 Remote Similarity NPC476608
0.6977 Remote Similarity NPC74995
0.6977 Remote Similarity NPC477924
0.6977 Remote Similarity NPC318495
0.6977 Remote Similarity NPC149550
0.6966 Remote Similarity NPC202389
0.6966 Remote Similarity NPC155521
0.6966 Remote Similarity NPC101462
0.6966 Remote Similarity NPC259858
0.6966 Remote Similarity NPC189972
0.6966 Remote Similarity NPC93590
0.6962 Remote Similarity NPC290367
0.6962 Remote Similarity NPC225415
0.6962 Remote Similarity NPC68656
0.6962 Remote Similarity NPC144650
0.6962 Remote Similarity NPC300593
0.6957 Remote Similarity NPC149224
0.6941 Remote Similarity NPC133580
0.6932 Remote Similarity NPC471266
0.6932 Remote Similarity NPC95124
0.6932 Remote Similarity NPC157895
0.6932 Remote Similarity NPC148685
0.6932 Remote Similarity NPC206062
0.6932 Remote Similarity NPC104120
0.6932 Remote Similarity NPC471514
0.6932 Remote Similarity NPC281880
0.6932 Remote Similarity NPC287749
0.6923 Remote Similarity NPC157257
0.6923 Remote Similarity NPC318390
0.6923 Remote Similarity NPC475251
0.6923 Remote Similarity NPC470360
0.6923 Remote Similarity NPC109528
0.6915 Remote Similarity NPC3345
0.6915 Remote Similarity NPC11216
0.6915 Remote Similarity NPC295668
0.6915 Remote Similarity NPC291484
0.6915 Remote Similarity NPC204188
0.6915 Remote Similarity NPC329596

  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 NPC311891 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
0.7349 Intermediate Similarity NPD8264 Approved
0.6897 Remote Similarity NPD7322 Clinical (unspecified phase)
0.686 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6926 Approved
0.6824 Remote Similarity NPD6924 Approved
0.6774 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6744 Remote Similarity NPD6942 Approved
0.6744 Remote Similarity NPD7339 Approved
0.6742 Remote Similarity NPD6930 Phase 2
0.6742 Remote Similarity NPD6931 Approved
0.6742 Remote Similarity NPD7332 Phase 2
0.6742 Remote Similarity NPD7514 Phase 3
0.6709 Remote Similarity NPD368 Approved
0.6667 Remote Similarity NPD6933 Approved
0.6629 Remote Similarity NPD7645 Phase 2
0.6629 Remote Similarity NPD6929 Approved
0.6588 Remote Similarity NPD7150 Approved
0.6588 Remote Similarity NPD7151 Approved
0.6588 Remote Similarity NPD7152 Approved
0.6556 Remote Similarity NPD7525 Registered
0.6556 Remote Similarity NPD7509 Discontinued
0.6522 Remote Similarity NPD6695 Phase 3
0.6517 Remote Similarity NPD7145 Approved
0.6484 Remote Similarity NPD6902 Approved
0.6471 Remote Similarity NPD7144 Approved
0.6471 Remote Similarity NPD7143 Approved
0.6452 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6413 Remote Similarity NPD3667 Approved
0.6404 Remote Similarity NPD5776 Phase 2
0.6404 Remote Similarity NPD6925 Approved
0.6404 Remote Similarity NPD6932 Approved
0.6383 Remote Similarity NPD6893 Approved
0.6374 Remote Similarity NPD4748 Discontinued
0.6364 Remote Similarity NPD342 Phase 1
0.6353 Remote Similarity NPD6922 Approved
0.6353 Remote Similarity NPD6923 Approved
0.6322 Remote Similarity NPD4732 Discontinued
0.6304 Remote Similarity NPD6898 Phase 1
0.6282 Remote Similarity NPD4219 Approved
0.6277 Remote Similarity NPD4786 Approved
0.625 Remote Similarity NPD4785 Approved
0.625 Remote Similarity NPD7750 Discontinued
0.625 Remote Similarity NPD7524 Approved
0.625 Remote Similarity NPD4784 Approved
0.6211 Remote Similarity NPD1696 Phase 3
0.6146 Remote Similarity NPD3618 Phase 1
0.6087 Remote Similarity NPD6683 Phase 2
0.6023 Remote Similarity NPD4243 Approved
0.6022 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6 Remote Similarity NPD7087 Discontinued
0.6 Remote Similarity NPD6079 Approved
0.5979 Remote Similarity NPD4623 Approved
0.5979 Remote Similarity NPD4519 Discontinued
0.5962 Remote Similarity NPD4225 Approved
0.596 Remote Similarity NPD5328 Approved
0.5943 Remote Similarity NPD5211 Phase 2
0.5943 Remote Similarity NPD7632 Discontinued
0.5941 Remote Similarity NPD4202 Approved
0.5941 Remote Similarity NPD5778 Approved
0.5941 Remote Similarity NPD5779 Approved
0.5938 Remote Similarity NPD3665 Phase 1
0.5938 Remote Similarity NPD3666 Approved
0.5938 Remote Similarity NPD3133 Approved
0.5914 Remote Similarity NPD4195 Approved
0.5842 Remote Similarity NPD7515 Phase 2
0.5842 Remote Similarity NPD7637 Suspended
0.5842 Remote Similarity NPD6411 Approved
0.5833 Remote Similarity NPD5141 Approved
0.5824 Remote Similarity NPD4190 Phase 3
0.5824 Remote Similarity NPD5275 Approved
0.5816 Remote Similarity NPD5279 Phase 3
0.5773 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5773 Remote Similarity NPD3668 Phase 3
0.5769 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5221 Approved
0.5769 Remote Similarity NPD5222 Approved
0.5755 Remote Similarity NPD5286 Approved
0.5755 Remote Similarity NPD7640 Approved
0.5755 Remote Similarity NPD5285 Approved
0.5755 Remote Similarity NPD4696 Approved
0.5755 Remote Similarity NPD7639 Approved
0.5743 Remote Similarity NPD7136 Phase 2
0.5714 Remote Similarity NPD5173 Approved
0.5714 Remote Similarity NPD4755 Approved
0.5701 Remote Similarity NPD5344 Discontinued
0.5701 Remote Similarity NPD5223 Approved
0.5684 Remote Similarity NPD4820 Approved
0.5684 Remote Similarity NPD4821 Approved
0.5684 Remote Similarity NPD4819 Approved
0.5684 Remote Similarity NPD4695 Discontinued
0.5684 Remote Similarity NPD4822 Approved
0.566 Remote Similarity NPD5290 Discontinued
0.566 Remote Similarity NPD7638 Approved
0.5648 Remote Similarity NPD5225 Approved
0.5648 Remote Similarity NPD5224 Approved
0.5648 Remote Similarity NPD5226 Approved
0.5648 Remote Similarity NPD4633 Approved
0.5644 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5644 Remote Similarity NPD6101 Approved
0.5644 Remote Similarity NPD4753 Phase 2
0.5638 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5631 Remote Similarity NPD6399 Phase 3
0.5619 Remote Similarity NPD4697 Phase 3
0.5607 Remote Similarity NPD4700 Approved
0.5603 Remote Similarity NPD6274 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