Structure

Physi-Chem Properties

Molecular Weight:  576.33
Volume:  605.572
LogP:  3.274
LogD:  3.17
LogS:  -4.404
# Rotatable Bonds:  13
TPSA:  138.82
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.205
Synthetic Accessibility Score:  5.232
Fsp3:  0.594
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.941
MDCK Permeability:  2.122361729561817e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.987
Human Intestinal Absorption (HIA):  0.307
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.214

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  94.8799819946289%
Volume Distribution (VD):  2.264
Pgp-substrate:  6.223459720611572%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.634
CYP2C19-inhibitor:  0.04
CYP2C19-substrate:  0.769
CYP2C9-inhibitor:  0.044
CYP2C9-substrate:  0.173
CYP2D6-inhibitor:  0.051
CYP2D6-substrate:  0.562
CYP3A4-inhibitor:  0.42
CYP3A4-substrate:  0.33

ADMET: Excretion

Clearance (CL):  4.166
Half-life (T1/2):  0.551

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.982
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.663
Rat Oral Acute Toxicity:  0.116
Maximum Recommended Daily Dose:  0.088
Skin Sensitization:  0.12
Carcinogencity:  0.084
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.039

Download Data

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

  Natural Product: NPC320552

Natural Product ID:  NPC320552
Common Name*:   3-Ethyl-2-Methoxy-5-Methyl-6-[(1E,5E,7E,11E)-3,7,9,11-Tetramethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxytrideca-1,5,7,11-Tetraenyl]Pyran-4-One
IUPAC Name:   3-ethyl-2-methoxy-5-methyl-6-[(1E,5E,7E,11E)-3,7,9,11-tetramethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytrideca-1,5,7,11-tetraenyl]pyran-4-one
Synonyms:  
Standard InCHIKey:  FHZSIAFPPYOOGE-NUECQFBTSA-N
Standard InCHI:  InChI=1S/C32H48O9/c1-9-20(5)30(41-32-29(37)28(36)27(35)25(17-33)40-32)21(6)16-19(4)13-11-12-18(3)14-15-24-22(7)26(34)23(10-2)31(38-8)39-24/h9,11,13-16,18,21,25,27-30,32-33,35-37H,10,12,17H2,1-8H3/b13-11+,15-14+,19-16+,20-9+/t18?,21?,25-,27-,28+,29-,30?,32+/m1/s1
SMILES:  CCC1=C(OC(=C(C1=O)C)C=CC(C)CC=CC(=CC(C)C(C(=CC)C)OC2C(C(C(C(O2)CO)O)O)O)C)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1817967
PubChem CID:   56668296
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides

*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
NPO24126 Streptomyces albus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18648803]
NPO24126 Streptomyces albus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19246195]
NPO24126.17 Streptomyces albus POR-04-15-053 Subspecies Streptomycetaceae Bacteria isolated from a suspension of marine sediment a depth 25 m at Punta Sagres (Portugal) 2004-AUG PMID[21718029]
NPO24126 Streptomyces albus Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21718029]
NPO24126 Streptomyces albus 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
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 240.0 nM PMID[535803]
NPT82 Cell Line MDA-MB-231 Homo sapiens TGI = 430.0 nM PMID[535803]
NPT82 Cell Line MDA-MB-231 Homo sapiens LC50 = 820.0 nM PMID[535803]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 380.0 nM PMID[535803]
NPT139 Cell Line HT-29 Homo sapiens TGI = 1230.0 nM PMID[535803]
NPT139 Cell Line HT-29 Homo sapiens LC50 = 4680.0 nM PMID[535803]
NPT81 Cell Line A549 Homo sapiens GI50 = 280.0 nM PMID[535803]
NPT81 Cell Line A549 Homo sapiens TGI = 520.0 nM PMID[535803]
NPT81 Cell Line A549 Homo sapiens LC50 = 1080.0 nM PMID[535803]

☑ 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 NPC320552 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
0.9767 High Similarity NPC327253
0.871 High Similarity NPC170204
0.8495 Intermediate Similarity NPC61201
0.8352 Intermediate Similarity NPC118077
0.8352 Intermediate Similarity NPC475186
0.8283 Intermediate Similarity NPC197736
0.828 Intermediate Similarity NPC6414
0.828 Intermediate Similarity NPC303451
0.8261 Intermediate Similarity NPC470137
0.8222 Intermediate Similarity NPC266718
0.8211 Intermediate Similarity NPC294293
0.8202 Intermediate Similarity NPC251026
0.8172 Intermediate Similarity NPC285588
0.8132 Intermediate Similarity NPC470124
0.8125 Intermediate Similarity NPC469543
0.8111 Intermediate Similarity NPC473315
0.8111 Intermediate Similarity NPC142111
0.8105 Intermediate Similarity NPC472196
0.8105 Intermediate Similarity NPC238090
0.8105 Intermediate Similarity NPC472195
0.8085 Intermediate Similarity NPC473311
0.8085 Intermediate Similarity NPC117596
0.8081 Intermediate Similarity NPC219038
0.8061 Intermediate Similarity NPC40182
0.8061 Intermediate Similarity NPC198422
0.8022 Intermediate Similarity NPC475035
0.8022 Intermediate Similarity NPC473308
0.8021 Intermediate Similarity NPC2003
0.8021 Intermediate Similarity NPC159698
0.8021 Intermediate Similarity NPC25701
0.8 Intermediate Similarity NPC222062
0.8 Intermediate Similarity NPC13171
0.8 Intermediate Similarity NPC110072
0.8 Intermediate Similarity NPC472125
0.8 Intermediate Similarity NPC472126
0.8 Intermediate Similarity NPC195510
0.8 Intermediate Similarity NPC471599
0.8 Intermediate Similarity NPC472124
0.798 Intermediate Similarity NPC306344
0.798 Intermediate Similarity NPC244878
0.798 Intermediate Similarity NPC255677
0.798 Intermediate Similarity NPC22149
0.7978 Intermediate Similarity NPC127295
0.7978 Intermediate Similarity NPC163362
0.7957 Intermediate Similarity NPC475037
0.7921 Intermediate Similarity NPC234304
0.7921 Intermediate Similarity NPC118761
0.7921 Intermediate Similarity NPC267869
0.7921 Intermediate Similarity NPC284929
0.7921 Intermediate Similarity NPC197541
0.79 Intermediate Similarity NPC475157
0.79 Intermediate Similarity NPC154132
0.79 Intermediate Similarity NPC28304
0.79 Intermediate Similarity NPC20673
0.79 Intermediate Similarity NPC298255
0.79 Intermediate Similarity NPC2313
0.79 Intermediate Similarity NPC471637
0.79 Intermediate Similarity NPC57586
0.79 Intermediate Similarity NPC475655
0.7895 Intermediate Similarity NPC307699
0.7885 Intermediate Similarity NPC133625
0.7879 Intermediate Similarity NPC151093
0.7872 Intermediate Similarity NPC471755
0.7872 Intermediate Similarity NPC471756
0.7857 Intermediate Similarity NPC288350
0.7857 Intermediate Similarity NPC173329
0.7849 Intermediate Similarity NPC47220
0.7849 Intermediate Similarity NPC208473
0.7849 Intermediate Similarity NPC186332
0.7843 Intermediate Similarity NPC86095
0.7822 Intermediate Similarity NPC261117
0.7822 Intermediate Similarity NPC310804
0.7816 Intermediate Similarity NPC315552
0.7812 Intermediate Similarity NPC477749
0.7789 Intermediate Similarity NPC477748
0.7788 Intermediate Similarity NPC473807
0.7742 Intermediate Similarity NPC475034
0.7732 Intermediate Similarity NPC280390
0.7727 Intermediate Similarity NPC229655
0.7723 Intermediate Similarity NPC98859
0.7723 Intermediate Similarity NPC4637
0.7708 Intermediate Similarity NPC118078
0.7708 Intermediate Similarity NPC202886
0.77 Intermediate Similarity NPC81483
0.77 Intermediate Similarity NPC61630
0.77 Intermediate Similarity NPC307517
0.77 Intermediate Similarity NPC169468
0.77 Intermediate Similarity NPC203627
0.7692 Intermediate Similarity NPC474285
0.7692 Intermediate Similarity NPC280367
0.7692 Intermediate Similarity NPC254538
0.7692 Intermediate Similarity NPC469469
0.7677 Intermediate Similarity NPC241911
0.7677 Intermediate Similarity NPC255410
0.7653 Intermediate Similarity NPC256368
0.7647 Intermediate Similarity NPC250545
0.7647 Intermediate Similarity NPC201191
0.7634 Intermediate Similarity NPC220167
0.7634 Intermediate Similarity NPC136699
0.7629 Intermediate Similarity NPC9447
0.7629 Intermediate Similarity NPC472197
0.7629 Intermediate Similarity NPC472199
0.76 Intermediate Similarity NPC474194
0.76 Intermediate Similarity NPC120299
0.76 Intermediate Similarity NPC475332
0.7596 Intermediate Similarity NPC315070
0.7586 Intermediate Similarity NPC316851
0.7579 Intermediate Similarity NPC125142
0.7576 Intermediate Similarity NPC101051
0.7576 Intermediate Similarity NPC300710
0.7556 Intermediate Similarity NPC133377
0.7553 Intermediate Similarity NPC242233
0.7551 Intermediate Similarity NPC320089
0.7526 Intermediate Similarity NPC470573
0.7526 Intermediate Similarity NPC231710
0.7526 Intermediate Similarity NPC65665
0.7526 Intermediate Similarity NPC216826
0.7526 Intermediate Similarity NPC120021
0.7526 Intermediate Similarity NPC270908
0.7525 Intermediate Similarity NPC124181
0.7525 Intermediate Similarity NPC475653
0.75 Intermediate Similarity NPC256230
0.75 Intermediate Similarity NPC472173
0.75 Intermediate Similarity NPC306041
0.75 Intermediate Similarity NPC137368
0.7475 Intermediate Similarity NPC472198
0.7453 Intermediate Similarity NPC472507
0.7444 Intermediate Similarity NPC110813
0.7429 Intermediate Similarity NPC82251
0.7426 Intermediate Similarity NPC153559
0.7419 Intermediate Similarity NPC123908
0.7419 Intermediate Similarity NPC10080
0.7404 Intermediate Similarity NPC151516
0.7396 Intermediate Similarity NPC313658
0.7396 Intermediate Similarity NPC316138
0.7396 Intermediate Similarity NPC45409
0.7386 Intermediate Similarity NPC132938
0.7379 Intermediate Similarity NPC198992
0.7379 Intermediate Similarity NPC154127
0.7374 Intermediate Similarity NPC475098
0.7374 Intermediate Similarity NPC189651
0.7374 Intermediate Similarity NPC159092
0.7368 Intermediate Similarity NPC477747
0.7368 Intermediate Similarity NPC477746
0.7368 Intermediate Similarity NPC471494
0.7364 Intermediate Similarity NPC475163
0.7353 Intermediate Similarity NPC473307
0.7347 Intermediate Similarity NPC474098
0.7347 Intermediate Similarity NPC177668
0.7347 Intermediate Similarity NPC475995
0.7333 Intermediate Similarity NPC469869
0.7327 Intermediate Similarity NPC54731
0.7321 Intermediate Similarity NPC473617
0.7321 Intermediate Similarity NPC473828
0.732 Intermediate Similarity NPC248312
0.7315 Intermediate Similarity NPC472508
0.7308 Intermediate Similarity NPC473596
0.7303 Intermediate Similarity NPC472174
0.7303 Intermediate Similarity NPC107654
0.7292 Intermediate Similarity NPC311163
0.729 Intermediate Similarity NPC193765
0.7283 Intermediate Similarity NPC321728
0.7273 Intermediate Similarity NPC476075
0.7273 Intermediate Similarity NPC472010
0.7273 Intermediate Similarity NPC476084
0.7273 Intermediate Similarity NPC206679
0.7273 Intermediate Similarity NPC114172
0.7273 Intermediate Similarity NPC471324
0.7264 Intermediate Similarity NPC476738
0.7264 Intermediate Similarity NPC239961
0.7264 Intermediate Similarity NPC476740
0.7263 Intermediate Similarity NPC475706
0.7257 Intermediate Similarity NPC219656
0.7255 Intermediate Similarity NPC266842
0.7255 Intermediate Similarity NPC278506
0.7255 Intermediate Similarity NPC476612
0.7255 Intermediate Similarity NPC476613
0.7245 Intermediate Similarity NPC249408
0.7245 Intermediate Similarity NPC133450
0.7245 Intermediate Similarity NPC104129
0.7245 Intermediate Similarity NPC309310
0.7238 Intermediate Similarity NPC309398
0.7228 Intermediate Similarity NPC241407
0.7228 Intermediate Similarity NPC108141
0.7228 Intermediate Similarity NPC291709
0.7222 Intermediate Similarity NPC316974
0.7222 Intermediate Similarity NPC40728
0.7216 Intermediate Similarity NPC199382
0.7212 Intermediate Similarity NPC197447
0.7212 Intermediate Similarity NPC476611
0.7212 Intermediate Similarity NPC169365
0.7204 Intermediate Similarity NPC470147
0.7204 Intermediate Similarity NPC133226
0.72 Intermediate Similarity NPC109406
0.7188 Intermediate Similarity NPC470658
0.7184 Intermediate Similarity NPC90819
0.7184 Intermediate Similarity NPC70733
0.7184 Intermediate Similarity NPC472015
0.7184 Intermediate Similarity NPC161855
0.7184 Intermediate Similarity NPC56071

  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 NPC320552 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
0.7879 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD7838 Discovery
0.7347 Intermediate Similarity NPD6698 Approved
0.7347 Intermediate Similarity NPD46 Approved
0.713 Intermediate Similarity NPD6686 Approved
0.6983 Remote Similarity NPD8513 Phase 3
0.6983 Remote Similarity NPD7503 Approved
0.6937 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6931 Remote Similarity NPD7983 Approved
0.6864 Remote Similarity NPD7830 Approved
0.6864 Remote Similarity NPD7829 Approved
0.6838 Remote Similarity NPD8517 Approved
0.6838 Remote Similarity NPD8515 Approved
0.6838 Remote Similarity NPD8516 Approved
0.6804 Remote Similarity NPD6110 Phase 1
0.6695 Remote Similarity NPD8444 Approved
0.6581 Remote Similarity NPD7641 Discontinued
0.6577 Remote Similarity NPD6412 Phase 2
0.6566 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6509 Remote Similarity NPD7839 Suspended
0.6475 Remote Similarity NPD8451 Approved
0.6423 Remote Similarity NPD8448 Approved
0.6417 Remote Similarity NPD8033 Approved
0.6333 Remote Similarity NPD8294 Approved
0.6333 Remote Similarity NPD8377 Approved
0.6311 Remote Similarity NPD7642 Approved
0.6303 Remote Similarity NPD7328 Approved
0.6303 Remote Similarity NPD7327 Approved
0.629 Remote Similarity NPD8074 Phase 3
0.6281 Remote Similarity NPD8378 Approved
0.6281 Remote Similarity NPD8380 Approved
0.6281 Remote Similarity NPD8296 Approved
0.6281 Remote Similarity NPD8379 Approved
0.6281 Remote Similarity NPD8335 Approved
0.6273 Remote Similarity NPD5344 Discontinued
0.627 Remote Similarity NPD8390 Approved
0.627 Remote Similarity NPD8392 Approved
0.627 Remote Similarity NPD8391 Approved
0.626 Remote Similarity NPD8299 Approved
0.626 Remote Similarity NPD8342 Approved
0.626 Remote Similarity NPD8341 Approved
0.626 Remote Similarity NPD8340 Approved
0.625 Remote Similarity NPD7516 Approved
0.6214 Remote Similarity NPD4251 Approved
0.6214 Remote Similarity NPD4250 Approved
0.621 Remote Similarity NPD7507 Approved
0.619 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6182 Remote Similarity NPD6648 Approved
0.614 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6132 Remote Similarity NPD7637 Suspended
0.6117 Remote Similarity NPD4249 Approved
0.6098 Remote Similarity NPD8080 Discontinued
0.6083 Remote Similarity NPD7500 Approved
0.6075 Remote Similarity NPD5778 Approved
0.6075 Remote Similarity NPD5779 Approved
0.6068 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6063 Remote Similarity NPD7319 Approved
0.6048 Remote Similarity NPD8328 Phase 3
0.6034 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6019 Remote Similarity NPD5282 Discontinued
0.6018 Remote Similarity NPD1407 Approved
0.6017 Remote Similarity NPD6053 Discontinued
0.5985 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5983 Remote Similarity NPD6371 Approved
0.598 Remote Similarity NPD7154 Phase 3
0.5966 Remote Similarity NPD8133 Approved
0.595 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5946 Remote Similarity NPD4225 Approved
0.5935 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5914 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5887 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5842 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5827 Remote Similarity NPD8273 Phase 1
0.5804 Remote Similarity NPD7638 Approved
0.5794 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5794 Remote Similarity NPD6101 Approved
0.5755 Remote Similarity NPD7524 Approved
0.5752 Remote Similarity NPD7640 Approved
0.5752 Remote Similarity NPD7639 Approved
0.5728 Remote Similarity NPD5209 Approved
0.5725 Remote Similarity NPD7260 Phase 2
0.5725 Remote Similarity NPD7266 Discontinued
0.5714 Remote Similarity NPD6370 Approved
0.57 Remote Similarity NPD4756 Discovery
0.5691 Remote Similarity NPD7505 Discontinued
0.5691 Remote Similarity NPD7115 Discovery
0.5691 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5688 Remote Similarity NPD6411 Approved
0.5644 Remote Similarity NPD4268 Approved
0.5644 Remote Similarity NPD4271 Approved
0.5625 Remote Similarity NPD1091 Approved
0.562 Remote Similarity NPD969 Suspended
0.5619 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5615 Remote Similarity NPD7736 Approved
0.5604 Remote Similarity NPD4246 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