Structure

Physi-Chem Properties

Molecular Weight:  327.15
Volume:  333.293
LogP:  2.381
LogD:  2.666
LogS:  -2.274
# Rotatable Bonds:  2
TPSA:  62.16
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.888
Synthetic Accessibility Score:  3.114
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.86
MDCK Permeability:  1.5040104699437506e-05
Pgp-inhibitor:  0.08
Pgp-substrate:  0.954
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.577
30% Bioavailability (F30%):  0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.94
Plasma Protein Binding (PPB):  84.74079132080078%
Volume Distribution (VD):  1.699
Pgp-substrate:  14.106813430786133%

ADMET: Metabolism

CYP1A2-inhibitor:  0.554
CYP1A2-substrate:  0.962
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.825
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.663
CYP2D6-inhibitor:  0.231
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.075
CYP3A4-substrate:  0.888

ADMET: Excretion

Clearance (CL):  14.96
Half-life (T1/2):  0.751

ADMET: Toxicity

hERG Blockers:  0.242
Human Hepatotoxicity (H-HT):  0.165
Drug-inuced Liver Injury (DILI):  0.599
AMES Toxicity:  0.452
Rat Oral Acute Toxicity:  0.428
Maximum Recommended Daily Dose:  0.952
Skin Sensitization:  0.804
Carcinogencity:  0.053
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.949

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC212794

Natural Product ID:  NPC212794
Common Name*:   Isoboldine
IUPAC Name:   (6aS)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,9-diol
Synonyms:   (+)-Isoboldine; Isoboldine
Standard InCHIKey:  LINHZVMHXABQLB-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C19H21NO4/c1-20-5-4-10-8-16(24-3)19(22)18-12-9-15(23-2)14(21)7-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1
SMILES:  COc1cc2c(cc1O)C[C@H]1c3c2c(O)c(OC)cc3CCN1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462880
PubChem CID:   133323
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(98)00534-2]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10978218]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[12932146]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota Resin n.a. n.a. PMID[1294696]
NPO28935 Ericameria laricifolia Species Asteraceae Eukaryota n.a. Sonoran Desert n.a. PMID[15043404]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. twig n.a. PMID[16204994]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[17020288]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota stem n.a. n.a. PMID[17081761]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. aerial part n.a. PMID[18991207]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota n.a. bark n.a. PMID[19329133]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota leaves Lai-I, Pingtung County, Taiwan 2005-May PMID[20704331]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota essential oil Tibet n.a. PMID[20944522]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota aerial parts n.a. n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[20949916]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22624550]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28541690]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota aerial parts Nanning, Guangxi Province, China 2014-OCT PMID[28753309]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. PMID[31861466]
NPO32610 nectandra salicifolia Species Lauraceae Eukaryota trunk bark lower montane rainforest in Costa Rica n.a. PMID[8786363]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[9170290]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6267 Gerbera jamesonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6267 Gerbera jamesonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5156 Hypoestes rosea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7389 Rhodiola atuntsuensis Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1079 Vachellia karroo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13929 Hypocrella bambusae Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18780 Diplacus aurantiacus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26851 Eupatorium rebaudianum 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]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29218 Ramalina farinacea Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13529 Aconitum saposhnikovii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15911 Streptomyces graminofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5156 Hypoestes rosea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14086 Parthenium confertum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14885 Lilium rubrum Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26228 Phymatopteris hastata Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11399 Balanites roxburghii Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29307 Loranthus longiflorus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13109 Ruptiliocarpon caracolito Species Lepidobotryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6615 Aplidium solidum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29411 Streptomyces nigrescens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13040 Veretillum cynomorium Species Veretillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27562 Coleus wulfenioides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16090 Panicum crus-galli Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1202 Psathyrotes ramosissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO862 Podocarpus elatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1079 Vachellia karroo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14223 Harpullia cupanioides Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14344 Trifolium diffusum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8632 Aralia hispida Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6730 Crossopteryx febrifuga Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12064 Lychnophora pinaster Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10616 Cyclobacterium marinum Species Cyclobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12296 Sphaerechinus granularis Species Toxopneustidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26549 Polanisia trachysperma Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14485 Eriocephalus kingesii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13241 Coprosma foetidissima Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28959 Cissus quadrangularis Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21110 Asplenium ceterach Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7036 Davidsonia pruriens Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20068 Fusarium striatum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6241 Girgensohnia oppositiflora Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12818 Lespedeza maximowiczi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13631 Microglossa pyrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29377 Callistemon speciosus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1516 Passiflora suberosa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3521 Geranium collinum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5040 Polygonatum polyanthemum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13755 Gonotheca helianthoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15098 Cyttaria johowii Species Cyttariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28549 Mentha incana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6229 Chenopodiastrum murale Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29144 Ormosia fordiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7878 Lysastrosoma anthosticta n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6848 Glycine clandestina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11833 Dyssodia anthemidifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18780 Diplacus aurantiacus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1946 Veronica stricta Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16079 Cephalaria leucantha Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14996 Lobelia syphilitica Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2770 Pyropolyporus fomentarius n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7389 Rhodiola atuntsuensis Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28935 Ericameria laricifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10936 Andira retusa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13929 Hypocrella bambusae Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6267 Gerbera jamesonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27256 Solanum boerhaavii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14366 Youngia japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2075 Zanthoxylum ocumarense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11607 Marrubium parviflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14639 Balanophora polyandra Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19931 Pyrus x nivalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15311 Cryptocarya chinensis Species Lauraceae 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
NPT1076 Cell Line B-cells IC50 = 29600.0 nM PMID[537716]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[537718]
NPT47 Individual Protein ATP-dependent DNA helicase Q1 Homo sapiens Potency = 25118.9 nM PMID[537718]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 28183.8 nM PMID[537718]
NPT1226 Individual Protein Caspase-7 Homo sapiens Potency = 31622.8 nM PMID[537718]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 11220.2 nM PMID[537718]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 12589.3 nM PMID[537719]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 14125.4 nM PMID[537718]
NPT583 Individual Protein Inositol monophosphatase 1 Rattus norvegicus Potency = 14125.4 nM PMID[537718]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 25118.9 nM PMID[537718]
NPT277 Individual Protein Caspase-1 Homo sapiens Potency = 31622.8 nM PMID[537718]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 3971.6 nM PMID[537718]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 35481.3 nM PMID[537718]
NPT583 Individual Protein Inositol monophosphatase 1 Rattus norvegicus Potency = 31622.8 nM PMID[537718]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[537719]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 31622.8 nM PMID[537718]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 19952.6 nM PMID[537718]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 6309.6 nM PMID[537719]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 25118.9 nM PMID[537719]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 3162.3 nM PMID[537720]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29855.4 nM PMID[537720]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 33498.3 nM PMID[537720]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 31622.8 nM PMID[537718]
NPT2740 Cell Line Neutrophils Inhibition > 50.0 % PMID[537721]
NPT2740 Cell Line Neutrophils IC50 = 5810.0 nM PMID[537721]
NPT27 Others Unspecified CC50 > 100000.0 nM PMID[537716]
NPT2 Others Unspecified IC50 = 24000.0 nM PMID[537716]
NPT2 Others Unspecified Ratio CC50/IC50 > 4.0 n.a. PMID[537716]
NPT2 Others Unspecified Ratio CC50/IC50 > 3.0 n.a. PMID[537716]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.668 ug.mL-1 PMID[537717]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.904 ug.mL-1 PMID[537717]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 31622.8 nM PMID[537718]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 31622.8 nM PMID[537718]
NPT2 Others Unspecified Potency = 28183.8 nM PMID[537718]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 12589.3 nM PMID[537718]

☑ 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 NPC212794 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 NPC477563
1.0 High Similarity NPC306843
1.0 High Similarity NPC253043
1.0 High Similarity NPC96603
1.0 High Similarity NPC196447
1.0 High Similarity NPC136508
1.0 High Similarity NPC13504
1.0 High Similarity NPC78222
0.9934 High Similarity NPC324144
0.987 High Similarity NPC306555
0.987 High Similarity NPC12053
0.987 High Similarity NPC81218
0.987 High Similarity NPC474931
0.987 High Similarity NPC158376
0.987 High Similarity NPC145832
0.987 High Similarity NPC117188
0.987 High Similarity NPC205421
0.9682 High Similarity NPC239775
0.9675 High Similarity NPC1229
0.9673 High Similarity NPC27410
0.9673 High Similarity NPC166014
0.9618 High Similarity NPC26240
0.9618 High Similarity NPC69712
0.9618 High Similarity NPC477562
0.956 High Similarity NPC229166
0.956 High Similarity NPC128560
0.956 High Similarity NPC199465
0.9539 High Similarity NPC325871
0.9539 High Similarity NPC99659
0.9497 High Similarity NPC477020
0.9497 High Similarity NPC192135
0.9497 High Similarity NPC66341
0.9494 High Similarity NPC168753
0.9494 High Similarity NPC118274
0.9441 High Similarity NPC114364
0.9441 High Similarity NPC320223
0.9416 High Similarity NPC476572
0.9359 High Similarity NPC60186
0.9304 High Similarity NPC81247
0.9304 High Similarity NPC35627
0.9304 High Similarity NPC476573
0.9268 High Similarity NPC116284
0.9264 High Similarity NPC474507
0.9216 High Similarity NPC326316
0.9216 High Similarity NPC81733
0.9207 High Similarity NPC477561
0.9207 High Similarity NPC312918
0.9207 High Similarity NPC155442
0.9207 High Similarity NPC476574
0.9141 High Similarity NPC476577
0.9141 High Similarity NPC148709
0.9141 High Similarity NPC173416
0.9125 High Similarity NPC298979
0.9119 High Similarity NPC302527
0.9119 High Similarity NPC167546
0.9119 High Similarity NPC16805
0.9096 High Similarity NPC135772
0.9062 High Similarity NPC24264
0.9062 High Similarity NPC476432
0.9038 High Similarity NPC276588
0.9038 High Similarity NPC110416
0.9038 High Similarity NPC207757
0.9038 High Similarity NPC204828
0.9038 High Similarity NPC295691
0.9038 High Similarity NPC39701
0.9038 High Similarity NPC172765
0.9038 High Similarity NPC278799
0.9038 High Similarity NPC189266
0.9038 High Similarity NPC127674
0.9038 High Similarity NPC54379
0.9038 High Similarity NPC2413
0.9038 High Similarity NPC184026
0.9038 High Similarity NPC469817
0.9038 High Similarity NPC5238
0.9038 High Similarity NPC249797
0.9038 High Similarity NPC193949
0.9026 High Similarity NPC192768
0.9026 High Similarity NPC88249
0.9026 High Similarity NPC151895
0.9026 High Similarity NPC97221
0.9026 High Similarity NPC220858
0.902 High Similarity NPC428
0.902 High Similarity NPC246587
0.902 High Similarity NPC135538
0.902 High Similarity NPC24233
0.902 High Similarity NPC476571
0.902 High Similarity NPC147390
0.9006 High Similarity NPC247389
0.9006 High Similarity NPC210918
0.9 High Similarity NPC225774
0.9 High Similarity NPC24465
0.8994 High Similarity NPC82763
0.8981 High Similarity NPC186063
0.8961 High Similarity NPC477565
0.8961 High Similarity NPC103379
0.8954 High Similarity NPC321505
0.8954 High Similarity NPC191376
0.8954 High Similarity NPC179825
0.8944 High Similarity NPC13916
0.8944 High Similarity NPC264850
0.8944 High Similarity NPC219341
0.8935 High Similarity NPC476576
0.8935 High Similarity NPC186546
0.8922 High Similarity NPC248642
0.8916 High Similarity NPC126284
0.8889 High Similarity NPC478093
0.8889 High Similarity NPC204947
0.8876 High Similarity NPC320088
0.8869 High Similarity NPC156576
0.8861 High Similarity NPC203784
0.8861 High Similarity NPC170503
0.8861 High Similarity NPC126519
0.8848 High Similarity NPC477558
0.8841 High Similarity NPC149090
0.8841 High Similarity NPC19520
0.8837 High Similarity NPC473589
0.8837 High Similarity NPC478092
0.8837 High Similarity NPC30182
0.8837 High Similarity NPC478091
0.8831 High Similarity NPC476151
0.8824 High Similarity NPC185838
0.8812 High Similarity NPC160298
0.8812 High Similarity NPC232924
0.8812 High Similarity NPC266753
0.8812 High Similarity NPC477559
0.8812 High Similarity NPC306902
0.8802 High Similarity NPC32154
0.8797 High Similarity NPC244112
0.878 High Similarity NPC6152
0.8773 High Similarity NPC150879
0.8773 High Similarity NPC210140
0.8765 High Similarity NPC57036
0.872 High Similarity NPC83198
0.872 High Similarity NPC204908
0.8712 High Similarity NPC124657
0.8696 High Similarity NPC235143
0.8696 High Similarity NPC205167
0.8696 High Similarity NPC205255
0.8696 High Similarity NPC271388
0.8696 High Similarity NPC230956
0.8696 High Similarity NPC119649
0.8696 High Similarity NPC249274
0.8683 High Similarity NPC241704
0.8671 High Similarity NPC26601
0.8667 High Similarity NPC152212
0.8655 High Similarity NPC214116
0.865 High Similarity NPC276944
0.865 High Similarity NPC232514
0.865 High Similarity NPC238530
0.865 High Similarity NPC169743
0.865 High Similarity NPC134858
0.8647 High Similarity NPC33902
0.8647 High Similarity NPC276674
0.8642 High Similarity NPC80759
0.8642 High Similarity NPC79402
0.8634 High Similarity NPC221864
0.8634 High Similarity NPC111485
0.8631 High Similarity NPC118633
0.8631 High Similarity NPC148693
0.8631 High Similarity NPC294790
0.8623 High Similarity NPC329969
0.8616 High Similarity NPC2295
0.8616 High Similarity NPC477564
0.8614 High Similarity NPC231371
0.8608 High Similarity NPC277669
0.8608 High Similarity NPC76213
0.8605 High Similarity NPC275680
0.8605 High Similarity NPC22115
0.859 High Similarity NPC16107
0.859 High Similarity NPC210437
0.859 High Similarity NPC476144
0.859 High Similarity NPC106295
0.859 High Similarity NPC51957
0.8589 High Similarity NPC233650
0.858 High Similarity NPC220961
0.8571 High Similarity NPC128019
0.8571 High Similarity NPC476567
0.8571 High Similarity NPC136860
0.8563 High Similarity NPC78284
0.8563 High Similarity NPC152680
0.8563 High Similarity NPC190783
0.8563 High Similarity NPC232386
0.8562 High Similarity NPC213206
0.8562 High Similarity NPC188163
0.8562 High Similarity NPC470925
0.8562 High Similarity NPC474915
0.8562 High Similarity NPC328750
0.8535 High Similarity NPC7467
0.8535 High Similarity NPC130941
0.8529 High Similarity NPC286119
0.8521 High Similarity NPC190461
0.8506 High Similarity NPC475754
0.8497 Intermediate Similarity NPC314682
0.8494 Intermediate Similarity NPC241055
0.8488 Intermediate Similarity NPC16357
0.8488 Intermediate Similarity NPC302245
0.8488 Intermediate Similarity NPC95426
0.8485 Intermediate Similarity NPC240841
0.8485 Intermediate Similarity NPC42549
0.8485 Intermediate Similarity NPC250846

  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 NPC212794 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
0.8889 High Similarity NPD2420 Approved
0.8889 High Similarity NPD2421 Approved
0.8606 High Similarity NPD27 Approved
0.8606 High Similarity NPD2489 Approved
0.8598 High Similarity NPD3051 Approved
0.859 High Similarity NPD4584 Approved
0.8562 High Similarity NPD4664 Clinical (unspecified phase)
0.8545 High Similarity NPD2970 Approved
0.8545 High Similarity NPD2969 Approved
0.848 Intermediate Similarity NPD8053 Approved
0.848 Intermediate Similarity NPD8054 Approved
0.8439 Intermediate Similarity NPD7906 Approved
0.8314 Intermediate Similarity NPD4577 Approved
0.8314 Intermediate Similarity NPD7312 Approved
0.8314 Intermediate Similarity NPD4578 Approved
0.8314 Intermediate Similarity NPD7311 Approved
0.8314 Intermediate Similarity NPD7313 Approved
0.8314 Intermediate Similarity NPD7310 Approved
0.8276 Intermediate Similarity NPD4663 Approved
0.8274 Intermediate Similarity NPD2898 Approved
0.8266 Intermediate Similarity NPD7309 Approved
0.8263 Intermediate Similarity NPD4010 Discontinued
0.8171 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8165 Intermediate Similarity NPD5241 Discontinued
0.8144 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD3845 Phase 1
0.8113 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD8252 Approved
0.807 Intermediate Similarity NPD8251 Approved
0.807 Intermediate Similarity NPD8099 Discontinued
0.8059 Intermediate Similarity NPD4481 Phase 3
0.8034 Intermediate Similarity NPD2490 Approved
0.8034 Intermediate Similarity NPD2488 Approved
0.8024 Intermediate Similarity NPD7831 Phase 2
0.8024 Intermediate Similarity NPD7833 Phase 2
0.8024 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD8156 Discontinued
0.8 Intermediate Similarity NPD7298 Approved
0.8 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD6788 Approved
0.7939 Intermediate Similarity NPD4773 Phase 2
0.7939 Intermediate Similarity NPD4772 Phase 2
0.7927 Intermediate Similarity NPD4017 Approved
0.7901 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD3450 Approved
0.7838 Intermediate Similarity NPD2494 Approved
0.7838 Intermediate Similarity NPD2493 Approved
0.7838 Intermediate Similarity NPD3452 Approved
0.7836 Intermediate Similarity NPD6071 Discontinued
0.7805 Intermediate Similarity NPD3640 Phase 3
0.7805 Intermediate Similarity NPD3639 Approved
0.7805 Intermediate Similarity NPD3641 Approved
0.7798 Intermediate Similarity NPD2560 Approved
0.7798 Intermediate Similarity NPD2563 Approved
0.7756 Intermediate Similarity NPD3110 Approved
0.7756 Intermediate Similarity NPD3109 Approved
0.7751 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD4583 Approved
0.7713 Intermediate Similarity NPD4582 Approved
0.7697 Intermediate Similarity NPD2971 Approved
0.7697 Intermediate Similarity NPD2968 Approved
0.7697 Intermediate Similarity NPD6030 Approved
0.7697 Intermediate Similarity NPD6031 Approved
0.7673 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4002 Approved
0.766 Intermediate Similarity NPD4004 Approved
0.7625 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD2973 Approved
0.7622 Intermediate Similarity NPD2974 Approved
0.7622 Intermediate Similarity NPD2975 Approved
0.7602 Intermediate Similarity NPD4055 Discovery
0.7564 Intermediate Similarity NPD5155 Approved
0.7564 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD5156 Approved
0.753 Intermediate Similarity NPD6090 Discontinued
0.7516 Intermediate Similarity NPD5718 Phase 2
0.75 Intermediate Similarity NPD3594 Approved
0.75 Intermediate Similarity NPD2605 Approved
0.75 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7047 Phase 3
0.75 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2606 Approved
0.75 Intermediate Similarity NPD4580 Approved
0.75 Intermediate Similarity NPD3595 Approved
0.75 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3060 Approved
0.7485 Intermediate Similarity NPD5177 Phase 3
0.7471 Intermediate Similarity NPD7802 Discontinued
0.7469 Intermediate Similarity NPD4726 Approved
0.7469 Intermediate Similarity NPD4725 Approved
0.7469 Intermediate Similarity NPD4721 Approved
0.7468 Intermediate Similarity NPD2674 Phase 3
0.7453 Intermediate Similarity NPD1753 Discontinued
0.745 Intermediate Similarity NPD6997 Phase 2
0.7436 Intermediate Similarity NPD3637 Approved
0.7436 Intermediate Similarity NPD3636 Approved
0.7436 Intermediate Similarity NPD3635 Approved
0.7435 Intermediate Similarity NPD4040 Phase 1
0.743 Intermediate Similarity NPD6297 Approved
0.7427 Intermediate Similarity NPD2978 Approved
0.7427 Intermediate Similarity NPD2977 Approved
0.7416 Intermediate Similarity NPD6042 Phase 2
0.7416 Intermediate Similarity NPD42 Phase 2
0.7396 Intermediate Similarity NPD4005 Discontinued
0.7394 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD6107 Approved
0.7365 Intermediate Similarity NPD1424 Approved
0.7362 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4474 Approved
0.7358 Intermediate Similarity NPD4475 Approved
0.733 Intermediate Similarity NPD3448 Approved
0.733 Intermediate Similarity NPD2491 Approved
0.733 Intermediate Similarity NPD3057 Approved
0.7314 Intermediate Similarity NPD4666 Phase 3
0.7308 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD3124 Discontinued
0.7296 Intermediate Similarity NPD3145 Approved
0.7296 Intermediate Similarity NPD3144 Approved
0.7284 Intermediate Similarity NPD6896 Approved
0.7284 Intermediate Similarity NPD6895 Approved
0.7278 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4236 Phase 3
0.7273 Intermediate Similarity NPD4237 Approved
0.7268 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD6851 Approved
0.7268 Intermediate Similarity NPD6853 Approved
0.7263 Intermediate Similarity NPD8095 Phase 1
0.7262 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD4123 Phase 3
0.7257 Intermediate Similarity NPD5709 Phase 3
0.7246 Intermediate Similarity NPD6667 Approved
0.7246 Intermediate Similarity NPD7124 Phase 2
0.7246 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6666 Approved
0.724 Intermediate Similarity NPD2972 Approved
0.724 Intermediate Similarity NPD3533 Approved
0.7232 Intermediate Similarity NPD4166 Phase 2
0.7229 Intermediate Similarity NPD5754 Discontinued
0.7219 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD4257 Approved
0.7212 Intermediate Similarity NPD4256 Phase 2
0.7209 Intermediate Similarity NPD6072 Discontinued
0.7202 Intermediate Similarity NPD7598 Phase 2
0.7193 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD6688 Approved
0.7191 Intermediate Similarity NPD6687 Approved
0.7186 Intermediate Similarity NPD5160 Discontinued
0.7182 Intermediate Similarity NPD7479 Phase 2
0.7178 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4727 Phase 1
0.7176 Intermediate Similarity NPD5976 Discontinued
0.7172 Intermediate Similarity NPD7827 Phase 1
0.716 Intermediate Similarity NPD7447 Phase 1
0.7135 Intermediate Similarity NPD6747 Phase 1
0.7135 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD4873 Discontinued
0.7127 Intermediate Similarity NPD5312 Approved
0.7127 Intermediate Similarity NPD5313 Approved
0.7126 Intermediate Similarity NPD6748 Discontinued
0.7126 Intermediate Similarity NPD5772 Approved
0.7126 Intermediate Similarity NPD5773 Approved
0.7124 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4420 Approved
0.7118 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7037 Approved
0.7102 Intermediate Similarity NPD5604 Discontinued
0.7101 Intermediate Similarity NPD7213 Phase 3
0.7101 Intermediate Similarity NPD7212 Phase 2
0.7099 Intermediate Similarity NPD2238 Phase 2
0.7089 Intermediate Similarity NPD3053 Approved
0.7089 Intermediate Similarity NPD3055 Approved
0.7086 Intermediate Similarity NPD5977 Approved
0.7086 Intermediate Similarity NPD5978 Approved
0.7083 Intermediate Similarity NPD3692 Discontinued
0.7081 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD4093 Discontinued
0.7076 Intermediate Similarity NPD1914 Approved
0.7076 Intermediate Similarity NPD2122 Discontinued
0.7074 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD1669 Approved
0.7066 Intermediate Similarity NPD4162 Approved
0.7065 Intermediate Similarity NPD7549 Discontinued
0.7062 Intermediate Similarity NPD7400 Phase 3
0.7059 Intermediate Similarity NPD7907 Approved
0.7052 Intermediate Similarity NPD4675 Approved
0.7052 Intermediate Similarity NPD4678 Approved
0.7049 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6612 Phase 2
0.7047 Intermediate Similarity NPD4107 Approved
0.7035 Intermediate Similarity NPD5676 Approved
0.7029 Intermediate Similarity NPD4585 Approved
0.7024 Intermediate Similarity NPD6331 Phase 2
0.7022 Intermediate Similarity NPD5677 Discontinued
0.7013 Intermediate Similarity NPD5303 Approved
0.7013 Intermediate Similarity NPD5304 Approved
0.7012 Intermediate Similarity NPD823 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