Structure

Physi-Chem Properties

Molecular Weight:  152.12
Volume:  170.557
LogP:  2.976
LogD:  2.411
LogS:  -3.332
# Rotatable Bonds:  1
TPSA:  12.53
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.415
Synthetic Accessibility Score:  3.909
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.505
MDCK Permeability:  2.0836225303355604e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.027
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.78
Plasma Protein Binding (PPB):  57.02291488647461%
Volume Distribution (VD):  1.644
Pgp-substrate:  41.51432418823242%

ADMET: Metabolism

CYP1A2-inhibitor:  0.158
CYP1A2-substrate:  0.492
CYP2C19-inhibitor:  0.047
CYP2C19-substrate:  0.878
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.292
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.879
CYP3A4-inhibitor:  0.044
CYP3A4-substrate:  0.286

ADMET: Excretion

Clearance (CL):  6.547
Half-life (T1/2):  0.533

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.393
Drug-inuced Liver Injury (DILI):  0.355
AMES Toxicity:  0.055
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.764
Skin Sensitization:  0.746
Carcinogencity:  0.598
Eye Corrosion:  0.99
Eye Irritation:  0.992
Respiratory Toxicity:  0.819

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

  Natural Product: NPC53403

Natural Product ID:  NPC53403
Common Name*:   CCEFMUBVSUDRLG-KXUCPTDWSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CCEFMUBVSUDRLG-KXUCPTDWSA-N
Standard InCHI:  InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
SMILES:  C=C(C)[C@@H]1CC[C@]2(C)[C@H](C1)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   6857487
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001729] Oxepanes

*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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)88710-5]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94055-X]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. flower n.a. DOI[10.3390/70200245]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10096857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO25415 Pseudopterogorgia kallos Species Gorgoniidae Eukaryota n.a. n.a. n.a. PMID[15128261]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO24744 Chloranthus tianmushanensis Species Chloranthaceae Eukaryota leaves n.a. n.a. PMID[18357995]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO24475 Aceriphyllum rossii n.a. n.a. n.a. n.a. n.a. n.a. PMID[19618898]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23186307]
NPO23805 Arnica nevadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23507152]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24617303]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25919052]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31836445]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730.2 Citrus medica var. sarcodactylis Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730.2 Citrus medica var. sarcodactylis Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730.2 Citrus medica var. sarcodactylis Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25529 Bursaria spinosa Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25390 Pterocarpus grandiflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7445 Pteris prolifera Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23453 Pheidole pallidula Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25090 Araujia sericifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25144 Artemisia monogyna Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24640 Echinops amplexicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24929 Aria pallescens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24556 Bassia butyracea Species Abylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25291 Lactarius scrobiculatus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25326 Dendrosenecio kilimanjari Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24744 Chloranthus tianmushanensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20833 Beyeria brevifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25187 Cladonia evansii Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26128 Clonostachys rosea Species Bionectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24830 Prosopis glandulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25234 Epaltes gariepina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18352 Anaxagorea clavata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24068 Prunus laurocerasus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25671 Gardenia fosbergii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23805 Arnica nevadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25699 Vitex madiensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25471 Chromolaena pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26042 Agnorhiza bolanderi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20823 Stenostomum lucidum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1794 Ilex affinis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28665 Sesbania punicea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24218 Fusarium gibbosum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24383 Ficus formosana Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24987 Simira eliezeriana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23567 Coccus fagi Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24599 Streptomyces althioticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7552 Alligator mississippiensis Species Alligatoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24291 Rhizobium phaseoli Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24675 Quercus aegilops Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24511 Dipterocarpus alatus Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24475 Aceriphyllum rossii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23691 Pyrosoma giganteum Species Pyrosomatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25415 Pseudopterogorgia kallos Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23963 Odixia angusta Species Asteraceae 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

☑ 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 NPC53403 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

  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 NPC53403 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

  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