Natural Product: NPC143011

Natural Product IDNPC143011
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 HSTZMXCBWJGKHG-GHHIHIOFSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 71752015
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes
        • [CHEMONTID:0000142] Stilbene glycosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey HSTZMXCBWJGKHG-GHHIHIOFSA-N
Standard InCHI InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16?,17-,18+,19?,20-/m1/s1
SMILES C(=Cc1cc(cc(c1)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O)O)/c1ccc(cc1)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   390.13 Volume:   380.673
?
Van der Waals volume.
Dense:   1.025 LogP:   1.322
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.626
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.253
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   19.0
TPSA:   139.84
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   6.0 Rings:   3.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.405 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.69 Fsp3:   0.3
MCE-18:   64.308
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.637 Fluc inhibitor:   0.94
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.044
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.735
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.473 Promiscuous compounds:   0.166

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.001 MDCK Permeability:   -5.076
Pgp-inhibitor:   0.0 Pgp-substrate:   0.031
PAMPA:   0.997
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.01
20% Bioavailability (F20%):   0.928 30% Bioavailability (F30%):   0.96
50% Bioavailability (F50%):   0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.066
Plasma Protein Binding (PPB):   84.299% Volume Distribution (VD):   -0.068
Fu: 17.044%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.994
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.074
BSEP inhibitor:   0.041

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.005 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.037 CYP2D6-substrate:   0.204
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.984
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.029
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  2.939 Half-life (T1/2):  3.115

ADMET: Toxicity

hERG Blockers:  0.184 hERG Blockers (10um):  0.477
Human Hepatotoxicity (H-HT):  0.76 Drug-induced Liver Injury (DILI):  0.23
AMES Toxicity:  0.735 Rat Oral Acute Toxicity:  0.091
Maximum Recommended Daily Dose:  0.428 Skin Sensitization:  0.742
Carcinogencity:  0.138 Eye Corrosion:  0.0
Eye Irritation:  0.602 Respiratory Toxicity:  0.05
Drug-induced Neurotoxicity:  0.128 Ototoxicity:  0.875
Hematotoxicity:  0.02 Drug-induced Nephrotoxicity:  0.23
Genotoxicity:  0.544 RPMI-8226 Immunitoxicity:  0.071
A549 Cytotoxicity:  0.413 Hek293 Cytotoxicity:  0.699
BCF:   0.729
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   3.328
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.073
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.085
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11076555]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[11459643]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[1517743]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO25611 Smilax china Species Smilacaceae Eukaryota stems n.a. n.a. PMID[16252910]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. root n.a. PMID[16564530]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[19948405]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. seed n.a. PMID[23672042]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[29359942]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[30384263]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[31944695]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[36483735]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[37631012]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[38354824]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[39199155]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots; Tubers n.a. n.a. PMID[7714535]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8277318]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29449 Boehmeria nivea Species Urticaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29449 Boehmeria nivea Species Urticaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29449 Boehmeria nivea Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7132 Smilax glabra Species Smilacaceae 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC143011 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC85799
1.0 High Similarity NPC303422
0.8571 High Similarity NPC242028
0.8571 High Similarity NPC203230
0.8545 High Similarity NPC218003
0.8246 Intermediate Similarity NPC294166
0.8246 Intermediate Similarity NPC115022
0.8136 Intermediate Similarity NPC212770
0.8 Intermediate Similarity NPC214910
0.7797 Intermediate Similarity NPC8497
0.7541 Intermediate Similarity NPC98777
0.7097 Intermediate Similarity NPC260681
0.7015 Intermediate Similarity NPC188555
0.6909 Remote Similarity NPC12308
0.678 Remote Similarity NPC26080
0.678 Remote Similarity NPC165686
0.6774 Remote Similarity NPC252169
0.6765 Remote Similarity NPC138350
0.6765 Remote Similarity NPC165482
0.6716 Remote Similarity NPC130496
0.6667 Remote Similarity NPC185778
0.6618 Remote Similarity NPC40664
0.6618 Remote Similarity NPC197723
0.6508 Remote Similarity NPC65530
0.6338 Remote Similarity NPC289346
0.6066 Remote Similarity NPC479028
0.6066 Remote Similarity NPC479031
0.6 Remote Similarity NPC142319
0.5938 Remote Similarity NPC59324
0.5909 Remote Similarity NPC604095
0.5882 Remote Similarity NPC57587
0.5875 Remote Similarity NPC59692
0.5833 Remote Similarity NPC238243
0.5769 Remote Similarity NPC233467
0.5735 Remote Similarity NPC189115
0.5696 Remote Similarity NPC157396
0.5634 Remote Similarity NPC88484
0.5606 Remote Similarity NPC478871
0.5606 Remote Similarity NPC478870
0.5606 Remote Similarity NPC478872
0.5606 Remote Similarity NPC478873
0.5556 Remote Similarity NPC484946
0.5556 Remote Similarity NPC484951
0.5556 Remote Similarity NPC280606
0.5541 Remote Similarity NPC168358
0.5526 Remote Similarity NPC89686
0.5526 Remote Similarity NPC257095
0.5513 Remote Similarity NPC100936
0.5513 Remote Similarity NPC1253
0.55 Remote Similarity NPC23431
0.5405 Remote Similarity NPC145319
0.5373 Remote Similarity NPC478888
0.5362 Remote Similarity NPC121001
0.5352 Remote Similarity NPC606353
0.5303 Remote Similarity NPC222455
0.5278 Remote Similarity NPC186406
0.5246 Remote Similarity NPC200092
0.5244 Remote Similarity NPC478877
0.5238 Remote Similarity NPC40377
0.5231 Remote Similarity NPC210015
0.5231 Remote Similarity NPC481303
0.5211 Remote Similarity NPC259767
0.5211 Remote Similarity NPC99233
0.5205 Remote Similarity NPC185103
0.52 Remote Similarity NPC166180
0.5172 Remote Similarity NPC212729
0.5172 Remote Similarity NPC604498
0.5167 Remote Similarity NPC152722
0.5161 Remote Similarity NPC145900
0.5152 Remote Similarity NPC479029
0.5125 Remote Similarity NPC152346
0.5125 Remote Similarity NPC197703
0.5119 Remote Similarity NPC478885
0.5085 Remote Similarity NPC269242
0.5085 Remote Similarity NPC484157
0.5082 Remote Similarity NPC60589
0.5082 Remote Similarity NPC469708
0.5079 Remote Similarity NPC166168
0.5079 Remote Similarity NPC214454
0.5077 Remote Similarity NPC205054
0.5072 Remote Similarity NPC469661
0.507 Remote Similarity NPC475084
0.5067 Remote Similarity NPC149244
0.5067 Remote Similarity NPC3293

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC143011 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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