Structure

Physi-Chem Properties

Molecular Weight:  232.15
Volume:  257.918
LogP:  4.3
LogD:  4.001
LogS:  -4.577
# Rotatable Bonds:  2
TPSA:  34.14
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.686
Synthetic Accessibility Score:  4.573
Fsp3:  0.6
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:  -4.709
MDCK Permeability:  2.0479523300309666e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.205
20% Bioavailability (F20%):  0.276
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  83.7506103515625%
Volume Distribution (VD):  2.167
Pgp-substrate:  7.090140342712402%

ADMET: Metabolism

CYP1A2-inhibitor:  0.838
CYP1A2-substrate:  0.269
CYP2C19-inhibitor:  0.317
CYP2C19-substrate:  0.758
CYP2C9-inhibitor:  0.196
CYP2C9-substrate:  0.545
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.378
CYP3A4-inhibitor:  0.58
CYP3A4-substrate:  0.351

ADMET: Excretion

Clearance (CL):  1.407
Half-life (T1/2):  0.633

ADMET: Toxicity

hERG Blockers:  0.197
Human Hepatotoxicity (H-HT):  0.92
Drug-inuced Liver Injury (DILI):  0.233
AMES Toxicity:  0.896
Rat Oral Acute Toxicity:  0.199
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.96
Carcinogencity:  0.286
Eye Corrosion:  0.565
Eye Irritation:  0.907
Respiratory Toxicity:  0.922

Download Data

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

  Natural Product: NPC183422

Natural Product ID:  NPC183422
Common Name*:   Lactarane
IUPAC Name:   (3aR,8R,8aR)-2,2,8-trimethyl-3,3a,8,8a-tetrahydro-1H-azulene-5,6-dicarbaldehyde
Synonyms:   Lactarane
Standard InCHIKey:  GUAUUIHVMRMGCT-MISXGVKJSA-N
Standard InCHI:  InChI=1S/C15H20O2/c1-10-4-12(8-16)13(9-17)5-11-6-15(2,3)7-14(10)11/h4-5,8-11,14H,6-7H2,1-3H3/t10-,11+,14+/m0/s1
SMILES:  O=CC1=C[C@H](C)[C@@H]2[C@H](C=C1C=O)CC(C2)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479316
PubChem CID:   14412869
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0003940] Organic oxides

*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
NPO1394 Penicillium sclerotigenum Species Aspergillaceae Eukaryota sclerotia n.a. n.a. PMID[10217735]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17432574]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO7991 Lactarius vellereus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7611 Sclerotium poriae cocos Species Typhulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10516 Lactarius piperatus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11327 Lactarius necator Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10516 Lactarius piperatus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7611 Sclerotium poriae cocos Species Typhulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29399 Microdochium nivale Species Microdochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7991 Lactarius vellereus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11327 Lactarius necator Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7991 Lactarius vellereus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29399 Microdochium nivale Species Microdochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1394 Penicillium sclerotigenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8243 Euphorbia supina Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7167 Hosta undulata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10516 Lactarius piperatus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3471 Suillellus luridus Species Boletaceae 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
NPT19 Organism Escherichia coli Escherichia coli Activity = 50.0 ug PMID[575371]
NPT729 Organism Micrococcus luteus Micrococcus luteus Activity = 15.0 ug PMID[575371]
NPT20 Organism Candida albicans Candida albicans Activity = 2.0 ug PMID[575371]

☑ 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 NPC183422 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
0.8507 High Similarity NPC162867
0.8507 High Similarity NPC61702
0.8429 Intermediate Similarity NPC263698
0.8 Intermediate Similarity NPC304983
0.7808 Intermediate Similarity NPC215481
0.7761 Intermediate Similarity NPC169275
0.7761 Intermediate Similarity NPC52449
0.7692 Intermediate Similarity NPC143834
0.7576 Intermediate Similarity NPC25853
0.7568 Intermediate Similarity NPC469796
0.7568 Intermediate Similarity NPC469793
0.75 Intermediate Similarity NPC261125
0.75 Intermediate Similarity NPC181195
0.75 Intermediate Similarity NPC473902
0.75 Intermediate Similarity NPC170793
0.746 Intermediate Similarity NPC95581
0.7429 Intermediate Similarity NPC4370
0.7429 Intermediate Similarity NPC290350
0.7424 Intermediate Similarity NPC259261
0.7403 Intermediate Similarity NPC471656
0.7385 Intermediate Similarity NPC208749
0.7385 Intermediate Similarity NPC281986
0.7385 Intermediate Similarity NPC22019
0.7385 Intermediate Similarity NPC321568
0.7368 Intermediate Similarity NPC228911
0.7353 Intermediate Similarity NPC165695
0.7353 Intermediate Similarity NPC167256
0.7344 Intermediate Similarity NPC188789
0.7273 Intermediate Similarity NPC94991
0.7273 Intermediate Similarity NPC30215
0.7273 Intermediate Similarity NPC266295
0.7246 Intermediate Similarity NPC212210
0.7206 Intermediate Similarity NPC475795
0.7183 Intermediate Similarity NPC475523
0.7143 Intermediate Similarity NPC187619
0.7121 Intermediate Similarity NPC267626
0.7121 Intermediate Similarity NPC55004
0.7121 Intermediate Similarity NPC49575
0.7101 Intermediate Similarity NPC32285
0.7083 Intermediate Similarity NPC155198
0.7083 Intermediate Similarity NPC469688
0.7051 Intermediate Similarity NPC90965
0.7031 Intermediate Similarity NPC296311
0.7027 Intermediate Similarity NPC474562
0.6962 Remote Similarity NPC474509
0.6957 Remote Similarity NPC213152
0.6957 Remote Similarity NPC97322
0.6933 Remote Similarity NPC144947
0.6914 Remote Similarity NPC470165
0.6901 Remote Similarity NPC268039
0.6866 Remote Similarity NPC193695
0.6866 Remote Similarity NPC230823
0.6849 Remote Similarity NPC469679
0.6842 Remote Similarity NPC211641
0.6842 Remote Similarity NPC128346
0.6842 Remote Similarity NPC474797
0.6842 Remote Similarity NPC75485
0.6842 Remote Similarity NPC474796
0.6842 Remote Similarity NPC309852
0.6842 Remote Similarity NPC219232
0.6842 Remote Similarity NPC329866
0.6842 Remote Similarity NPC168975
0.68 Remote Similarity NPC181204
0.6769 Remote Similarity NPC45283
0.6757 Remote Similarity NPC469677
0.6753 Remote Similarity NPC77501
0.6719 Remote Similarity NPC30433
0.6716 Remote Similarity NPC20603
0.6714 Remote Similarity NPC260573
0.6712 Remote Similarity NPC193770
0.6711 Remote Similarity NPC474228
0.6711 Remote Similarity NPC303613
0.6667 Remote Similarity NPC250539
0.6667 Remote Similarity NPC260040
0.6667 Remote Similarity NPC209431
0.6667 Remote Similarity NPC472959
0.6667 Remote Similarity NPC251929
0.6667 Remote Similarity NPC96551
0.6667 Remote Similarity NPC2634
0.6667 Remote Similarity NPC100809
0.6667 Remote Similarity NPC472967
0.6667 Remote Similarity NPC285594
0.6667 Remote Similarity NPC307176
0.6667 Remote Similarity NPC265782
0.6667 Remote Similarity NPC266159
0.6623 Remote Similarity NPC238146
0.6623 Remote Similarity NPC167049
0.6623 Remote Similarity NPC469691
0.6613 Remote Similarity NPC195246
0.6613 Remote Similarity NPC22098
0.6613 Remote Similarity NPC276009
0.6588 Remote Similarity NPC475772
0.6579 Remote Similarity NPC54123
0.6579 Remote Similarity NPC5701
0.6575 Remote Similarity NPC92327
0.6575 Remote Similarity NPC176171
0.6567 Remote Similarity NPC275472
0.6562 Remote Similarity NPC228776
0.6543 Remote Similarity NPC164218
0.6538 Remote Similarity NPC475771
0.6538 Remote Similarity NPC251435
0.6538 Remote Similarity NPC469669
0.6538 Remote Similarity NPC469678
0.6533 Remote Similarity NPC139397
0.6522 Remote Similarity NPC311852
0.6515 Remote Similarity NPC37644
0.6515 Remote Similarity NPC23117
0.6515 Remote Similarity NPC295777
0.6515 Remote Similarity NPC69898
0.6515 Remote Similarity NPC474141
0.6512 Remote Similarity NPC477710
0.65 Remote Similarity NPC473912
0.65 Remote Similarity NPC115515
0.6494 Remote Similarity NPC470045
0.6494 Remote Similarity NPC251705
0.6494 Remote Similarity NPC300940
0.6494 Remote Similarity NPC92909
0.6494 Remote Similarity NPC470044
0.6494 Remote Similarity NPC107783
0.6486 Remote Similarity NPC176107
0.6486 Remote Similarity NPC136813
0.6479 Remote Similarity NPC294304
0.6479 Remote Similarity NPC228574
0.6462 Remote Similarity NPC234829
0.6456 Remote Similarity NPC19907
0.6456 Remote Similarity NPC250621
0.6456 Remote Similarity NPC469646
0.6456 Remote Similarity NPC4509
0.6456 Remote Similarity NPC69408
0.6456 Remote Similarity NPC474463
0.6452 Remote Similarity NPC49088
0.6447 Remote Similarity NPC282593
0.6447 Remote Similarity NPC35734
0.6447 Remote Similarity NPC159577
0.6438 Remote Similarity NPC470329
0.6438 Remote Similarity NPC251118
0.6437 Remote Similarity NPC41217
0.6429 Remote Similarity NPC309825
0.642 Remote Similarity NPC283789
0.6418 Remote Similarity NPC63396
0.6418 Remote Similarity NPC202850
0.641 Remote Similarity NPC159497
0.641 Remote Similarity NPC255021
0.6404 Remote Similarity NPC250575
0.64 Remote Similarity NPC310992
0.64 Remote Similarity NPC167527
0.6393 Remote Similarity NPC106819
0.6389 Remote Similarity NPC472306
0.6389 Remote Similarity NPC124112
0.6389 Remote Similarity NPC288253
0.6386 Remote Similarity NPC142683
0.6377 Remote Similarity NPC115385
0.6375 Remote Similarity NPC86917
0.6375 Remote Similarity NPC276769
0.6364 Remote Similarity NPC471751
0.6364 Remote Similarity NPC22182
0.6364 Remote Similarity NPC106309
0.6364 Remote Similarity NPC474884
0.6364 Remote Similarity NPC234707
0.6364 Remote Similarity NPC306168
0.6364 Remote Similarity NPC305501
0.6364 Remote Similarity NPC477711
0.6364 Remote Similarity NPC49946
0.6364 Remote Similarity NPC2946
0.6364 Remote Similarity NPC115023
0.6364 Remote Similarity NPC470078
0.6353 Remote Similarity NPC280203
0.6349 Remote Similarity NPC262558
0.6349 Remote Similarity NPC323445
0.6349 Remote Similarity NPC8610
0.6341 Remote Similarity NPC45495
0.6341 Remote Similarity NPC471514
0.6338 Remote Similarity NPC127582
0.6338 Remote Similarity NPC47840
0.6338 Remote Similarity NPC234264
0.6329 Remote Similarity NPC293803
0.6329 Remote Similarity NPC68624
0.6329 Remote Similarity NPC472256
0.6329 Remote Similarity NPC255650
0.6329 Remote Similarity NPC473171
0.6316 Remote Similarity NPC261398
0.6316 Remote Similarity NPC22301
0.6316 Remote Similarity NPC256846
0.631 Remote Similarity NPC474976
0.631 Remote Similarity NPC474790
0.6301 Remote Similarity NPC4638
0.6301 Remote Similarity NPC150162
0.6301 Remote Similarity NPC6697
0.6296 Remote Similarity NPC474056
0.6296 Remote Similarity NPC59436
0.6296 Remote Similarity NPC207186
0.6286 Remote Similarity NPC60772
0.6282 Remote Similarity NPC310608
0.6279 Remote Similarity NPC168248
0.6279 Remote Similarity NPC6247
0.6269 Remote Similarity NPC14002
0.6269 Remote Similarity NPC268564
0.6265 Remote Similarity NPC4166
0.6265 Remote Similarity NPC136150
0.625 Remote Similarity NPC476317

  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 NPC183422 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
0.7027 Intermediate Similarity NPD5276 Approved
0.6842 Remote Similarity NPD4058 Approved
0.6842 Remote Similarity NPD4687 Approved
0.6842 Remote Similarity NPD5733 Approved
0.6667 Remote Similarity NPD4747 Approved
0.6667 Remote Similarity NPD4691 Approved
0.6533 Remote Similarity NPD4137 Phase 3
0.6279 Remote Similarity NPD5279 Phase 3
0.6118 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6104 Remote Similarity NPD6923 Approved
0.6104 Remote Similarity NPD6922 Approved
0.6056 Remote Similarity NPD287 Approved
0.6027 Remote Similarity NPD4191 Approved
0.6027 Remote Similarity NPD4193 Approved
0.6027 Remote Similarity NPD4192 Approved
0.6027 Remote Similarity NPD4194 Approved
0.6026 Remote Similarity NPD7143 Approved
0.6026 Remote Similarity NPD7144 Approved
0.6 Remote Similarity NPD6926 Approved
0.6 Remote Similarity NPD5209 Approved
0.6 Remote Similarity NPD6924 Approved
0.5974 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5949 Remote Similarity NPD7152 Approved
0.5949 Remote Similarity NPD7151 Approved
0.5949 Remote Similarity NPD7150 Approved
0.5909 Remote Similarity NPD5280 Approved
0.5909 Remote Similarity NPD4694 Approved
0.5904 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5867 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5862 Remote Similarity NPD3133 Approved
0.5862 Remote Similarity NPD3666 Approved
0.5862 Remote Similarity NPD3665 Phase 1
0.5854 Remote Similarity NPD6933 Approved
0.5851 Remote Similarity NPD4697 Phase 3
0.5833 Remote Similarity NPD4195 Approved
0.5814 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5814 Remote Similarity NPD4223 Phase 3
0.5814 Remote Similarity NPD4221 Approved
0.5783 Remote Similarity NPD5776 Phase 2
0.5783 Remote Similarity NPD6932 Approved
0.5783 Remote Similarity NPD6925 Approved
0.5778 Remote Similarity NPD6672 Approved
0.5778 Remote Similarity NPD4518 Approved
0.5778 Remote Similarity NPD5737 Approved
0.5775 Remote Similarity NPD4219 Approved
0.5761 Remote Similarity NPD6079 Approved
0.573 Remote Similarity NPD5690 Phase 2
0.573 Remote Similarity NPD7334 Approved
0.573 Remote Similarity NPD6684 Approved
0.573 Remote Similarity NPD3618 Phase 1
0.573 Remote Similarity NPD7521 Approved
0.573 Remote Similarity NPD6409 Approved
0.573 Remote Similarity NPD7146 Approved
0.573 Remote Similarity NPD5330 Approved
0.5714 Remote Similarity NPD5328 Approved
0.5714 Remote Similarity NPD7145 Approved
0.5714 Remote Similarity NPD4753 Phase 2
0.5682 Remote Similarity NPD4786 Approved
0.5682 Remote Similarity NPD4197 Approved
0.5652 Remote Similarity NPD5207 Approved
0.5652 Remote Similarity NPD5692 Phase 3
0.5652 Remote Similarity NPD4096 Approved
0.5647 Remote Similarity NPD6929 Approved
0.5647 Remote Similarity NPD6683 Phase 2
0.5632 Remote Similarity NPD3667 Approved
0.5618 Remote Similarity NPD1696 Phase 3
0.5618 Remote Similarity NPD5329 Approved
0.5604 Remote Similarity NPD6903 Approved
0.5604 Remote Similarity NPD7513 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