Structure

Physi-Chem Properties

Molecular Weight:  236.18
Volume:  257.271
LogP:  3.293
LogD:  2.616
LogS:  -3.897
# Rotatable Bonds:  1
TPSA:  32.76
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.561
Synthetic Accessibility Score:  4.741
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.567
MDCK Permeability:  1.586793950991705e-05
Pgp-inhibitor:  0.391
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.163
30% Bioavailability (F30%):  0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.138
Plasma Protein Binding (PPB):  94.39571380615234%
Volume Distribution (VD):  1.859
Pgp-substrate:  4.275073051452637%

ADMET: Metabolism

CYP1A2-inhibitor:  0.101
CYP1A2-substrate:  0.409
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.857
CYP2C9-inhibitor:  0.245
CYP2C9-substrate:  0.092
CYP2D6-inhibitor:  0.02
CYP2D6-substrate:  0.339
CYP3A4-inhibitor:  0.139
CYP3A4-substrate:  0.366

ADMET: Excretion

Clearance (CL):  4.445
Half-life (T1/2):  0.389

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.321
Drug-inuced Liver Injury (DILI):  0.375
AMES Toxicity:  0.058
Rat Oral Acute Toxicity:  0.264
Maximum Recommended Daily Dose:  0.234
Skin Sensitization:  0.133
Carcinogencity:  0.135
Eye Corrosion:  0.468
Eye Irritation:  0.946
Respiratory Toxicity:  0.939

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC471454

Natural Product ID:  NPC471454
Common Name*:   (3R*,4S*,5R*,7R*,10R*)-3,4-Epoxy-11-Hydroxy-1-Pseudoguaiene
IUPAC Name:   2-[(1aS,1bR,3R,6R,7aR)-1b,6-dimethyl-2,3,4,5,6,7a-hexahydro-1aH-azuleno[1,2-b]oxiren-3-yl]propan-2-ol
Synonyms:  
Standard InCHIKey:  ZQLNOTQNTMDOGU-ZUJPDMLGSA-N
Standard InCHI:  InChI=1S/C15H24O2/c1-9-5-6-10(14(2,3)16)8-15(4)11(9)7-12-13(15)17-12/h7,9-10,12-13,16H,5-6,8H2,1-4H3/t9-,10-,12-,13-,15-/m1/s1
SMILES:  CC1CCC(CC2(C1=CC3C2O3)C)C(C)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL249846
PubChem CID:   23642712
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002873] Pseudoguaianes

*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
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. formosan soft coral n.a. PMID[17845002]
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[24370010]
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[9722490]
NPO13916 Nephthea erecta Species Nephtheidae 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
NPT139 Cell Line HT-29 Homo sapiens ED50 > 10.0 ug ml-1 PMID[496094]
NPT168 Cell Line P388 Mus musculus ED50 > 10.0 ug ml-1 PMID[496094]

☑ 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 NPC471454 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
0.8481 Intermediate Similarity NPC471661
0.8272 Intermediate Similarity NPC471340
0.7867 Intermediate Similarity NPC305698
0.7763 Intermediate Similarity NPC74722
0.7763 Intermediate Similarity NPC304690
0.7733 Intermediate Similarity NPC259299
0.7733 Intermediate Similarity NPC477791
0.7722 Intermediate Similarity NPC60818
0.7722 Intermediate Similarity NPC23231
0.7671 Intermediate Similarity NPC211291
0.7671 Intermediate Similarity NPC133368
0.7667 Intermediate Similarity NPC220221
0.7662 Intermediate Similarity NPC470041
0.7654 Intermediate Similarity NPC477089
0.7625 Intermediate Similarity NPC476317
0.7625 Intermediate Similarity NPC126969
0.7595 Intermediate Similarity NPC471659
0.7586 Intermediate Similarity NPC91248
0.7564 Intermediate Similarity NPC471662
0.7561 Intermediate Similarity NPC204270
0.7532 Intermediate Similarity NPC144647
0.7531 Intermediate Similarity NPC84360
0.75 Intermediate Similarity NPC472255
0.75 Intermediate Similarity NPC472253
0.75 Intermediate Similarity NPC136813
0.7471 Intermediate Similarity NPC471657
0.7471 Intermediate Similarity NPC45957
0.7468 Intermediate Similarity NPC329763
0.7436 Intermediate Similarity NPC129630
0.7416 Intermediate Similarity NPC209816
0.7416 Intermediate Similarity NPC197107
0.7407 Intermediate Similarity NPC268111
0.7407 Intermediate Similarity NPC170148
0.7407 Intermediate Similarity NPC471658
0.7403 Intermediate Similarity NPC167527
0.7375 Intermediate Similarity NPC471525
0.7375 Intermediate Similarity NPC190859
0.7368 Intermediate Similarity NPC272125
0.7368 Intermediate Similarity NPC469328
0.7363 Intermediate Similarity NPC470010
0.7363 Intermediate Similarity NPC323008
0.7363 Intermediate Similarity NPC262133
0.7363 Intermediate Similarity NPC470013
0.7356 Intermediate Similarity NPC255143
0.7356 Intermediate Similarity NPC137253
0.7349 Intermediate Similarity NPC476701
0.7342 Intermediate Similarity NPC477084
0.7342 Intermediate Similarity NPC41886
0.7342 Intermediate Similarity NPC471660
0.7333 Intermediate Similarity NPC140233
0.7333 Intermediate Similarity NPC287744
0.7333 Intermediate Similarity NPC249034
0.7326 Intermediate Similarity NPC222634
0.7326 Intermediate Similarity NPC116613
0.7317 Intermediate Similarity NPC476703
0.7317 Intermediate Similarity NPC186109
0.7317 Intermediate Similarity NPC31037
0.7308 Intermediate Similarity NPC269841
0.7303 Intermediate Similarity NPC4986
0.7294 Intermediate Similarity NPC259858
0.7273 Intermediate Similarity NPC59442
0.7273 Intermediate Similarity NPC471796
0.7262 Intermediate Similarity NPC474592
0.7262 Intermediate Similarity NPC186072
0.726 Intermediate Similarity NPC83838
0.726 Intermediate Similarity NPC143810
0.725 Intermediate Similarity NPC476709
0.7241 Intermediate Similarity NPC119001
0.7237 Intermediate Similarity NPC205618
0.7237 Intermediate Similarity NPC469326
0.7237 Intermediate Similarity NPC61503
0.7237 Intermediate Similarity NPC261782
0.7237 Intermediate Similarity NPC19569
0.7234 Intermediate Similarity NPC109556
0.7229 Intermediate Similarity NPC474005
0.7222 Intermediate Similarity NPC37607
0.7222 Intermediate Similarity NPC301969
0.7215 Intermediate Similarity NPC254845
0.7215 Intermediate Similarity NPC471781
0.7209 Intermediate Similarity NPC477667
0.7209 Intermediate Similarity NPC231601
0.7209 Intermediate Similarity NPC472473
0.72 Intermediate Similarity NPC50435
0.72 Intermediate Similarity NPC473508
0.72 Intermediate Similarity NPC279200
0.7195 Intermediate Similarity NPC256720
0.7195 Intermediate Similarity NPC271070
0.7195 Intermediate Similarity NPC236228
0.7179 Intermediate Similarity NPC224532
0.7174 Intermediate Similarity NPC198853
0.7174 Intermediate Similarity NPC472467
0.7174 Intermediate Similarity NPC477131
0.7159 Intermediate Similarity NPC261253
0.7159 Intermediate Similarity NPC471219
0.7159 Intermediate Similarity NPC474045
0.7159 Intermediate Similarity NPC477668
0.7143 Intermediate Similarity NPC133698
0.7143 Intermediate Similarity NPC131209
0.7143 Intermediate Similarity NPC325869
0.7143 Intermediate Similarity NPC233295
0.7143 Intermediate Similarity NPC327815
0.7126 Intermediate Similarity NPC160517
0.7126 Intermediate Similarity NPC154893
0.7126 Intermediate Similarity NPC83702
0.7126 Intermediate Similarity NPC186155
0.7126 Intermediate Similarity NPC16887
0.7126 Intermediate Similarity NPC78673
0.7126 Intermediate Similarity NPC37005
0.7126 Intermediate Similarity NPC53011
0.7123 Intermediate Similarity NPC475830
0.7123 Intermediate Similarity NPC10017
0.7111 Intermediate Similarity NPC49783
0.7111 Intermediate Similarity NPC299527
0.7108 Intermediate Similarity NPC476439
0.7105 Intermediate Similarity NPC110241
0.7097 Intermediate Similarity NPC240838
0.7093 Intermediate Similarity NPC472465
0.7089 Intermediate Similarity NPC217570
0.7089 Intermediate Similarity NPC90115
0.7089 Intermediate Similarity NPC329989
0.7089 Intermediate Similarity NPC239373
0.7083 Intermediate Similarity NPC274396
0.7073 Intermediate Similarity NPC113639
0.7067 Intermediate Similarity NPC210346
0.7067 Intermediate Similarity NPC63111
0.7065 Intermediate Similarity NPC135776
0.7059 Intermediate Similarity NPC474739
0.7053 Intermediate Similarity NPC221615
0.7045 Intermediate Similarity NPC471795
0.7037 Intermediate Similarity NPC143576
0.7037 Intermediate Similarity NPC477085
0.7037 Intermediate Similarity NPC14352
0.7037 Intermediate Similarity NPC234527
0.7033 Intermediate Similarity NPC295668
0.7024 Intermediate Similarity NPC470944
0.7021 Intermediate Similarity NPC72204
0.7013 Intermediate Similarity NPC477009
0.7013 Intermediate Similarity NPC238352
0.7011 Intermediate Similarity NPC260852
0.7011 Intermediate Similarity NPC475789
0.6988 Remote Similarity NPC152017
0.6988 Remote Similarity NPC310643
0.6977 Remote Similarity NPC474752
0.6977 Remote Similarity NPC15978
0.6977 Remote Similarity NPC7505
0.6977 Remote Similarity NPC474759
0.6977 Remote Similarity NPC82986
0.6977 Remote Similarity NPC474683
0.6977 Remote Similarity NPC474731
0.697 Remote Similarity NPC179891
0.6966 Remote Similarity NPC61527
0.6966 Remote Similarity NPC281316
0.6966 Remote Similarity NPC67493
0.6966 Remote Similarity NPC56593
0.6957 Remote Similarity NPC472468
0.6957 Remote Similarity NPC234335
0.6957 Remote Similarity NPC475972
0.6951 Remote Similarity NPC309178
0.6947 Remote Similarity NPC347923
0.6947 Remote Similarity NPC205143
0.6947 Remote Similarity NPC476057
0.6947 Remote Similarity NPC182811
0.6947 Remote Similarity NPC477949
0.6941 Remote Similarity NPC86971
0.6933 Remote Similarity NPC471081
0.6933 Remote Similarity NPC127824
0.6932 Remote Similarity NPC474047
0.6923 Remote Similarity NPC32922
0.6923 Remote Similarity NPC311736
0.6923 Remote Similarity NPC267027
0.6923 Remote Similarity NPC470819
0.6923 Remote Similarity NPC162309
0.6915 Remote Similarity NPC52044
0.6915 Remote Similarity NPC67584
0.6915 Remote Similarity NPC304886
0.6914 Remote Similarity NPC477086
0.6914 Remote Similarity NPC477792
0.6914 Remote Similarity NPC477087
0.6914 Remote Similarity NPC469343
0.6897 Remote Similarity NPC155521
0.6889 Remote Similarity NPC476948
0.6889 Remote Similarity NPC474765
0.6883 Remote Similarity NPC300593
0.6883 Remote Similarity NPC309300
0.6875 Remote Similarity NPC274458
0.6875 Remote Similarity NPC101622
0.6875 Remote Similarity NPC79449
0.6875 Remote Similarity NPC474957
0.6875 Remote Similarity NPC472947
0.6867 Remote Similarity NPC12696
0.6867 Remote Similarity NPC313185
0.6867 Remote Similarity NPC265921
0.6867 Remote Similarity NPC215215
0.6867 Remote Similarity NPC469678
0.6867 Remote Similarity NPC85831
0.6867 Remote Similarity NPC475771
0.6867 Remote Similarity NPC469669
0.6863 Remote Similarity NPC15551
0.686 Remote Similarity NPC472470
0.686 Remote Similarity NPC324772

  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 NPC471454 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
0.7303 Intermediate Similarity NPD1695 Approved
0.7011 Intermediate Similarity NPD6695 Phase 3
0.6932 Remote Similarity NPD7338 Clinical (unspecified phase)
0.686 Remote Similarity NPD6930 Phase 2
0.686 Remote Similarity NPD6931 Approved
0.686 Remote Similarity NPD7332 Phase 2
0.6747 Remote Similarity NPD6926 Approved
0.6747 Remote Similarity NPD6924 Approved
0.6744 Remote Similarity NPD6929 Approved
0.6703 Remote Similarity NPD7524 Approved
0.6703 Remote Similarity NPD7750 Discontinued
0.6703 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6699 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD7514 Phase 3
0.6628 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6902 Approved
0.6591 Remote Similarity NPD6898 Phase 1
0.6588 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6588 Remote Similarity NPD6933 Approved
0.6582 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6569 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6531 Remote Similarity NPD7638 Approved
0.6512 Remote Similarity NPD6932 Approved
0.6512 Remote Similarity NPD6925 Approved
0.6512 Remote Similarity NPD5776 Phase 2
0.6489 Remote Similarity NPD7838 Discovery
0.6484 Remote Similarity NPD6893 Approved
0.6477 Remote Similarity NPD7509 Discontinued
0.6465 Remote Similarity NPD7639 Approved
0.6465 Remote Similarity NPD7640 Approved
0.6437 Remote Similarity NPD7145 Approved
0.6421 Remote Similarity NPD7087 Discontinued
0.641 Remote Similarity NPD368 Approved
0.6392 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6683 Phase 2
0.6316 Remote Similarity NPD46 Approved
0.6316 Remote Similarity NPD6698 Approved
0.6304 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6304 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6289 Remote Similarity NPD5282 Discontinued
0.6279 Remote Similarity NPD6942 Approved
0.6279 Remote Similarity NPD7339 Approved
0.6265 Remote Similarity NPD6922 Approved
0.6265 Remote Similarity NPD6923 Approved
0.6264 Remote Similarity NPD7154 Phase 3
0.6264 Remote Similarity NPD5362 Discontinued
0.6238 Remote Similarity NPD5344 Discontinued
0.6237 Remote Similarity NPD4249 Approved
0.6211 Remote Similarity NPD6051 Approved
0.619 Remote Similarity NPD7143 Approved
0.619 Remote Similarity NPD7144 Approved
0.617 Remote Similarity NPD4250 Approved
0.617 Remote Similarity NPD4251 Approved
0.6163 Remote Similarity NPD4785 Approved
0.6163 Remote Similarity NPD4784 Approved
0.6146 Remote Similarity NPD5785 Approved
0.6139 Remote Similarity NPD6648 Approved
0.6118 Remote Similarity NPD4243 Approved
0.6118 Remote Similarity NPD7151 Approved
0.6118 Remote Similarity NPD7150 Approved
0.6118 Remote Similarity NPD7152 Approved
0.6111 Remote Similarity NPD4820 Approved
0.6111 Remote Similarity NPD4819 Approved
0.6111 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4822 Approved
0.6111 Remote Similarity NPD4821 Approved
0.6111 Remote Similarity NPD7525 Registered
0.6092 Remote Similarity NPD8264 Approved
0.6082 Remote Similarity NPD7637 Suspended
0.6078 Remote Similarity NPD4159 Approved
0.6053 Remote Similarity NPD342 Phase 1
0.6047 Remote Similarity NPD4732 Discontinued
0.6 Remote Similarity NPD6640 Phase 3
0.5979 Remote Similarity NPD3168 Discontinued
0.5978 Remote Similarity NPD3667 Approved
0.5978 Remote Similarity NPD5209 Approved
0.5963 Remote Similarity NPD6053 Discontinued
0.5934 Remote Similarity NPD4748 Discontinued
0.5914 Remote Similarity NPD5331 Approved
0.5914 Remote Similarity NPD5332 Approved
0.5909 Remote Similarity NPD5275 Approved
0.5909 Remote Similarity NPD4190 Phase 3
0.5889 Remote Similarity NPD4271 Approved
0.5889 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5889 Remote Similarity NPD4268 Approved
0.5882 Remote Similarity NPD4225 Approved
0.587 Remote Similarity NPD4790 Discontinued
0.587 Remote Similarity NPD5369 Approved
0.5865 Remote Similarity NPD7632 Discontinued
0.5851 Remote Similarity NPD3665 Phase 1
0.5851 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5851 Remote Similarity NPD4786 Approved
0.5851 Remote Similarity NPD3666 Approved
0.5851 Remote Similarity NPD3133 Approved
0.5824 Remote Similarity NPD7645 Phase 2
0.5824 Remote Similarity NPD4195 Approved
0.5816 Remote Similarity NPD7136 Phase 2
0.5806 Remote Similarity NPD4269 Approved
0.5806 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5806 Remote Similarity NPD4270 Approved
0.5789 Remote Similarity NPD1694 Approved
0.5789 Remote Similarity NPD1696 Phase 3
0.5741 Remote Similarity NPD6686 Approved
0.5729 Remote Similarity NPD5786 Approved
0.5728 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5702 Remote Similarity NPD7328 Approved
0.5702 Remote Similarity NPD7327 Approved
0.5701 Remote Similarity NPD6008 Approved
0.57 Remote Similarity NPD5778 Approved
0.57 Remote Similarity NPD6399 Phase 3
0.57 Remote Similarity NPD5779 Approved
0.569 Remote Similarity NPD8033 Approved
0.5688 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5652 Remote Similarity NPD7516 Approved
0.5638 Remote Similarity NPD4221 Approved
0.5638 Remote Similarity NPD6435 Approved
0.5638 Remote Similarity NPD4223 Phase 3
0.5636 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5363 Approved
0.5614 Remote Similarity NPD7115 Discovery
0.5603 Remote Similarity NPD8377 Approved
0.5603 Remote Similarity NPD8294 Approved
0.5603 Remote Similarity NPD7741 Discontinued
0.56 Remote Similarity NPD7983 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