Structure

Physi-Chem Properties

Molecular Weight:  254.15
Volume:  263.475
LogP:  2.388
LogD:  2.246
LogS:  -3.47
# Rotatable Bonds:  0
TPSA:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.53
Synthetic Accessibility Score:  5.31
Fsp3:  0.786
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:  -4.769
MDCK Permeability:  6.864363967906684e-05
Pgp-inhibitor:  0.668
Pgp-substrate:  0.03
Human Intestinal Absorption (HIA):  0.037
20% Bioavailability (F20%):  0.051
30% Bioavailability (F30%):  0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.517
Plasma Protein Binding (PPB):  89.00352478027344%
Volume Distribution (VD):  1.053
Pgp-substrate:  4.375322341918945%

ADMET: Metabolism

CYP1A2-inhibitor:  0.04
CYP1A2-substrate:  0.096
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.401
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.529
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.132
CYP3A4-inhibitor:  0.113
CYP3A4-substrate:  0.278

ADMET: Excretion

Clearance (CL):  4.988
Half-life (T1/2):  0.696

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.681
Drug-inuced Liver Injury (DILI):  0.375
AMES Toxicity:  0.896
Rat Oral Acute Toxicity:  0.624
Maximum Recommended Daily Dose:  0.941
Skin Sensitization:  0.879
Carcinogencity:  0.82
Eye Corrosion:  0.052
Eye Irritation:  0.451
Respiratory Toxicity:  0.268

Download Data

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

  Natural Product: NPC49392

Natural Product ID:  NPC49392
Common Name*:   (1R,5S,11R,14S,E)-14-Hydroxy-5-Methyl-4,15-Dioxabicyclo[9.3.1]Pentadec-9-En-3-One
IUPAC Name:   (1R,2E,7S,11R,12S)-12-hydroxy-7-methyl-8,15-dioxabicyclo[9.3.1]pentadec-2-en-9-one
Synonyms:  
Standard InCHIKey:  FDJDTDDUDZAAFP-GDHSIMSHSA-N
Standard InCHI:  InChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/b6-4+/t10-,11-,12-,13+/m0/s1
SMILES:  C[C@H]1CCC/C=C/[C@H]2CC[C@@H]([C@@H](CC(=O)O1)O2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2407403
PubChem CID:   70678632
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
NPO4417 Aspergillus ostianus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17994702]
NPO4417 Aspergillus ostianus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[1807834]
NPO4417 Aspergillus ostianus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18078344]
NPO4417 Aspergillus ostianus Species Aspergillaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 81200.0 nM PMID[569912]

☑ 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 NPC49392 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
1.0 High Similarity NPC190400
0.9041 High Similarity NPC473948
0.8493 Intermediate Similarity NPC42526
0.8333 Intermediate Similarity NPC271921
0.8333 Intermediate Similarity NPC104537
0.8333 Intermediate Similarity NPC22101
0.8333 Intermediate Similarity NPC148192
0.8333 Intermediate Similarity NPC127091
0.8333 Intermediate Similarity NPC330426
0.8219 Intermediate Similarity NPC141481
0.8219 Intermediate Similarity NPC324981
0.8219 Intermediate Similarity NPC48218
0.8219 Intermediate Similarity NPC473559
0.8082 Intermediate Similarity NPC473829
0.8082 Intermediate Similarity NPC475443
0.8026 Intermediate Similarity NPC470435
0.8025 Intermediate Similarity NPC474252
0.8 Intermediate Similarity NPC476660
0.7952 Intermediate Similarity NPC182383
0.7901 Intermediate Similarity NPC297440
0.7895 Intermediate Similarity NPC320119
0.7875 Intermediate Similarity NPC475210
0.7875 Intermediate Similarity NPC469747
0.7875 Intermediate Similarity NPC263574
0.7867 Intermediate Similarity NPC470436
0.7867 Intermediate Similarity NPC473772
0.7857 Intermediate Similarity NPC47937
0.7838 Intermediate Similarity NPC26500
0.7838 Intermediate Similarity NPC25298
0.7838 Intermediate Similarity NPC99619
0.7778 Intermediate Similarity NPC40812
0.775 Intermediate Similarity NPC127526
0.775 Intermediate Similarity NPC11796
0.775 Intermediate Similarity NPC218817
0.7692 Intermediate Similarity NPC474321
0.7692 Intermediate Similarity NPC187761
0.7692 Intermediate Similarity NPC83895
0.7692 Intermediate Similarity NPC473489
0.7683 Intermediate Similarity NPC21693
0.7683 Intermediate Similarity NPC236649
0.7647 Intermediate Similarity NPC69082
0.7647 Intermediate Similarity NPC478112
0.7647 Intermediate Similarity NPC279267
0.7647 Intermediate Similarity NPC469483
0.7647 Intermediate Similarity NPC469910
0.7632 Intermediate Similarity NPC130618
0.7632 Intermediate Similarity NPC475982
0.7625 Intermediate Similarity NPC474278
0.7625 Intermediate Similarity NPC475711
0.7625 Intermediate Similarity NPC474026
0.7625 Intermediate Similarity NPC281296
0.7619 Intermediate Similarity NPC243618
0.7619 Intermediate Similarity NPC70424
0.7619 Intermediate Similarity NPC163093
0.7614 Intermediate Similarity NPC327760
0.76 Intermediate Similarity NPC478100
0.7595 Intermediate Similarity NPC60718
0.7595 Intermediate Similarity NPC473582
0.759 Intermediate Similarity NPC11383
0.759 Intermediate Similarity NPC474959
0.759 Intermediate Similarity NPC310450
0.759 Intermediate Similarity NPC475046
0.7586 Intermediate Similarity NPC130359
0.7586 Intermediate Similarity NPC14901
0.7568 Intermediate Similarity NPC476657
0.7568 Intermediate Similarity NPC476654
0.7568 Intermediate Similarity NPC476655
0.7561 Intermediate Similarity NPC47653
0.7558 Intermediate Similarity NPC178215
0.7534 Intermediate Similarity NPC54925
0.7531 Intermediate Similarity NPC248775
0.7531 Intermediate Similarity NPC121200
0.7531 Intermediate Similarity NPC182292
0.7529 Intermediate Similarity NPC471567
0.7529 Intermediate Similarity NPC103284
0.7529 Intermediate Similarity NPC1083
0.7529 Intermediate Similarity NPC132496
0.7529 Intermediate Similarity NPC107986
0.7529 Intermediate Similarity NPC231009
0.7529 Intermediate Similarity NPC120398
0.7529 Intermediate Similarity NPC283085
0.7529 Intermediate Similarity NPC322529
0.7529 Intermediate Similarity NPC82795
0.7529 Intermediate Similarity NPC477013
0.7529 Intermediate Similarity NPC223871
0.7529 Intermediate Similarity NPC473669
0.7529 Intermediate Similarity NPC473478
0.7529 Intermediate Similarity NPC66346
0.7529 Intermediate Similarity NPC286338
0.7529 Intermediate Similarity NPC473651
0.7529 Intermediate Similarity NPC110710
0.7529 Intermediate Similarity NPC477014
0.75 Intermediate Similarity NPC470313
0.75 Intermediate Similarity NPC81896
0.75 Intermediate Similarity NPC229799
0.75 Intermediate Similarity NPC261377
0.75 Intermediate Similarity NPC253801
0.75 Intermediate Similarity NPC321919
0.75 Intermediate Similarity NPC473311
0.75 Intermediate Similarity NPC38295
0.75 Intermediate Similarity NPC473500
0.75 Intermediate Similarity NPC156089
0.75 Intermediate Similarity NPC474232
0.75 Intermediate Similarity NPC284472
0.75 Intermediate Similarity NPC286770
0.75 Intermediate Similarity NPC308567
0.75 Intermediate Similarity NPC255592
0.7471 Intermediate Similarity NPC233551
0.7471 Intermediate Similarity NPC40376
0.7471 Intermediate Similarity NPC48338
0.7471 Intermediate Similarity NPC21208
0.7471 Intermediate Similarity NPC280621
0.7471 Intermediate Similarity NPC20339
0.7471 Intermediate Similarity NPC476803
0.7468 Intermediate Similarity NPC326504
0.7467 Intermediate Similarity NPC476659
0.7467 Intermediate Similarity NPC478101
0.7467 Intermediate Similarity NPC284447
0.7467 Intermediate Similarity NPC476656
0.7442 Intermediate Similarity NPC112685
0.7442 Intermediate Similarity NPC219498
0.7442 Intermediate Similarity NPC171174
0.7442 Intermediate Similarity NPC240695
0.7442 Intermediate Similarity NPC107717
0.7442 Intermediate Similarity NPC62118
0.7442 Intermediate Similarity NPC103523
0.7442 Intermediate Similarity NPC210218
0.7442 Intermediate Similarity NPC134865
0.7442 Intermediate Similarity NPC204686
0.7442 Intermediate Similarity NPC114694
0.7442 Intermediate Similarity NPC473687
0.7442 Intermediate Similarity NPC134885
0.7442 Intermediate Similarity NPC232555
0.7442 Intermediate Similarity NPC142117
0.7442 Intermediate Similarity NPC475581
0.7442 Intermediate Similarity NPC231096
0.7442 Intermediate Similarity NPC308412
0.7442 Intermediate Similarity NPC477015
0.7442 Intermediate Similarity NPC134807
0.7439 Intermediate Similarity NPC470148
0.7439 Intermediate Similarity NPC470149
0.7439 Intermediate Similarity NPC180725
0.7432 Intermediate Similarity NPC470320
0.7416 Intermediate Similarity NPC6099
0.7416 Intermediate Similarity NPC303230
0.7416 Intermediate Similarity NPC114345
0.7412 Intermediate Similarity NPC9868
0.7412 Intermediate Similarity NPC474251
0.7412 Intermediate Similarity NPC156804
0.7412 Intermediate Similarity NPC158756
0.7397 Intermediate Similarity NPC201939
0.7397 Intermediate Similarity NPC113293
0.7397 Intermediate Similarity NPC321838
0.7386 Intermediate Similarity NPC280612
0.7381 Intermediate Similarity NPC180363
0.7381 Intermediate Similarity NPC73310
0.7381 Intermediate Similarity NPC145914
0.7381 Intermediate Similarity NPC89555
0.7381 Intermediate Similarity NPC473712
0.7381 Intermediate Similarity NPC65930
0.7381 Intermediate Similarity NPC11332
0.7381 Intermediate Similarity NPC473529
0.7381 Intermediate Similarity NPC329829
0.7381 Intermediate Similarity NPC475159
0.7381 Intermediate Similarity NPC475690
0.7381 Intermediate Similarity NPC473780
0.7381 Intermediate Similarity NPC131002
0.7381 Intermediate Similarity NPC94875
0.7375 Intermediate Similarity NPC260396
0.7368 Intermediate Similarity NPC478097
0.7356 Intermediate Similarity NPC473995
0.7356 Intermediate Similarity NPC472007
0.7349 Intermediate Similarity NPC133226
0.7349 Intermediate Similarity NPC469920
0.7349 Intermediate Similarity NPC233377
0.7349 Intermediate Similarity NPC470147
0.7342 Intermediate Similarity NPC326024
0.7342 Intermediate Similarity NPC144419
0.7333 Intermediate Similarity NPC19769
0.7333 Intermediate Similarity NPC326268
0.7333 Intermediate Similarity NPC255863
0.7333 Intermediate Similarity NPC478099
0.7333 Intermediate Similarity NPC136164
0.7333 Intermediate Similarity NPC469692
0.7333 Intermediate Similarity NPC320089
0.7333 Intermediate Similarity NPC469645
0.7333 Intermediate Similarity NPC478098
0.7333 Intermediate Similarity NPC245947
0.7333 Intermediate Similarity NPC318420
0.7326 Intermediate Similarity NPC329615
0.7326 Intermediate Similarity NPC470755
0.7326 Intermediate Similarity NPC329838
0.7317 Intermediate Similarity NPC318481
0.7317 Intermediate Similarity NPC473471
0.7308 Intermediate Similarity NPC202011
0.7303 Intermediate Similarity NPC239517
0.7294 Intermediate Similarity NPC144415
0.7294 Intermediate Similarity NPC185256
0.7294 Intermediate Similarity NPC69469
0.7284 Intermediate Similarity NPC127118

  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 NPC49392 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
0.75 Intermediate Similarity NPD46 Approved
0.75 Intermediate Similarity NPD6698 Approved
0.7432 Intermediate Similarity NPD3197 Phase 1
0.7222 Intermediate Similarity NPD7983 Approved
0.6809 Remote Similarity NPD1698 Clinical (unspecified phase)
0.68 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4269 Approved
0.6782 Remote Similarity NPD4270 Approved
0.6761 Remote Similarity NPD3172 Approved
0.6744 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4252 Approved
0.6739 Remote Similarity NPD5785 Approved
0.6705 Remote Similarity NPD7154 Phase 3
0.6667 Remote Similarity NPD3196 Approved
0.6667 Remote Similarity NPD3195 Phase 2
0.6667 Remote Similarity NPD3730 Approved
0.6667 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD5369 Approved
0.6667 Remote Similarity NPD4266 Approved
0.6667 Remote Similarity NPD3728 Approved
0.6667 Remote Similarity NPD3194 Approved
0.663 Remote Similarity NPD5764 Clinical (unspecified phase)
0.663 Remote Similarity NPD6101 Approved
0.6598 Remote Similarity NPD4225 Approved
0.6596 Remote Similarity NPD5778 Approved
0.6596 Remote Similarity NPD5779 Approved
0.6591 Remote Similarity NPD6435 Approved
0.6562 Remote Similarity NPD7839 Suspended
0.6559 Remote Similarity NPD7838 Discovery
0.6556 Remote Similarity NPD5363 Approved
0.6538 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6109 Phase 1
0.6512 Remote Similarity NPD4268 Approved
0.6512 Remote Similarity NPD4271 Approved
0.65 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6411 Approved
0.6471 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6371 Approved
0.6429 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6408 Remote Similarity NPD6686 Approved
0.6374 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4821 Approved
0.6364 Remote Similarity NPD4822 Approved
0.6364 Remote Similarity NPD5368 Approved
0.6364 Remote Similarity NPD4820 Approved
0.6364 Remote Similarity NPD4819 Approved
0.6353 Remote Similarity NPD8039 Approved
0.6333 Remote Similarity NPD5362 Discontinued
0.6322 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6316 Remote Similarity NPD585 Clinical (unspecified phase)
0.6306 Remote Similarity NPD8517 Approved
0.6306 Remote Similarity NPD8515 Approved
0.6306 Remote Similarity NPD8513 Phase 3
0.6306 Remote Similarity NPD8516 Approved
0.6304 Remote Similarity NPD4249 Approved
0.6286 Remote Similarity NPD622 Approved
0.6279 Remote Similarity NPD819 Approved
0.6279 Remote Similarity NPD818 Approved
0.6277 Remote Similarity NPD5370 Suspended
0.625 Remote Similarity NPD28 Approved
0.625 Remote Similarity NPD5345 Clinical (unspecified phase)
0.625 Remote Similarity NPD29 Approved
0.6239 Remote Similarity NPD7115 Discovery
0.6237 Remote Similarity NPD4250 Approved
0.6237 Remote Similarity NPD4251 Approved
0.6207 Remote Similarity NPD4756 Discovery
0.6197 Remote Similarity NPD3173 Approved
0.6196 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6184 Remote Similarity NPD8959 Approved
0.6161 Remote Similarity NPD8444 Approved
0.6136 Remote Similarity NPD3732 Approved
0.6087 Remote Similarity NPD8451 Approved
0.6053 Remote Similarity NPD7830 Approved
0.6053 Remote Similarity NPD7829 Approved
0.6053 Remote Similarity NPD7642 Approved
0.6044 Remote Similarity NPD5209 Approved
0.6034 Remote Similarity NPD8448 Approved
0.6034 Remote Similarity NPD8074 Phase 3
0.6022 Remote Similarity NPD1694 Approved
0.602 Remote Similarity NPD5282 Discontinued
0.598 Remote Similarity NPD5344 Discontinued
0.5979 Remote Similarity NPD7637 Suspended
0.5948 Remote Similarity NPD8273 Phase 1
0.5904 Remote Similarity NPD898 Approved
0.5904 Remote Similarity NPD897 Approved
0.5904 Remote Similarity NPD896 Approved
0.59 Remote Similarity NPD4228 Discovery
0.59 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5897 Remote Similarity NPD69 Approved
0.5897 Remote Similarity NPD9119 Approved
0.5882 Remote Similarity NPD8390 Approved
0.5882 Remote Similarity NPD8391 Approved
0.5882 Remote Similarity NPD8392 Approved
0.587 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5862 Remote Similarity NPD8341 Approved
0.5862 Remote Similarity NPD8299 Approved
0.5862 Remote Similarity NPD8340 Approved
0.5862 Remote Similarity NPD8342 Approved
0.5854 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5844 Remote Similarity NPD73 Approved
0.5833 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5833 Remote Similarity NPD6421 Discontinued
0.5833 Remote Similarity NPD5343 Approved
0.5811 Remote Similarity NPD6927 Phase 3
0.5806 Remote Similarity NPD5332 Approved
0.5806 Remote Similarity NPD5331 Approved
0.5802 Remote Similarity NPD8961 Approved
0.5789 Remote Similarity NPD6422 Discontinued
0.5783 Remote Similarity NPD3704 Approved
0.5775 Remote Similarity NPD3174 Discontinued
0.5775 Remote Similarity NPD4222 Approved
0.5773 Remote Similarity NPD1695 Approved
0.5769 Remote Similarity NPD9118 Approved
0.5761 Remote Similarity NPD4790 Discontinued
0.5758 Remote Similarity NPD6399 Phase 3
0.5745 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5741 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5667 Remote Similarity NPD7319 Approved
0.5638 Remote Similarity NPD6110 Phase 1
0.5631 Remote Similarity NPD7638 Approved
0.5614 Remote Similarity NPD7641 Discontinued
0.561 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5603 Remote Similarity NPD6921 Approved
0.56 Remote Similarity NPD7966 Clinical (unspecified phase)

  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