Natural Product: NPC38455

Natural Product IDNPC38455
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Hulupinic Acid
IUPAC Name 4,5-dihydroxy-2,2-bis(3-methylbut-2-enyl)cyclopent-4-ene-1,3-dione
Synonyms Hulupinic Acid
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL454528
PubChem CID 12310637
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0003889] Vinylogous acids

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 KKNXLCGOZLVUHL-UHFFFAOYSA-N
Standard InCHI InChI=1S/C15H20O4/c1-9(2)5-7-15(8-6-10(3)4)13(18)11(16)12(17)14(15)19/h5-6,16-17H,7-8H2,1-4H3
SMILES CC(=CCC1(CC=C(C)C)C(=O)C(=C(C1=O)O)O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   264.14 Volume:   281.418
?
Van der Waals volume.
Dense:   0.939 LogP:   3.442
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.194
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.359
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   9.0
TPSA:   74.6
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   2.0 Rings:   1.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.604 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.391 Fsp3:   0.467
MCE-18:   13.091
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.202 Fluc inhibitor:   0.001
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.065
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.16
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.922 Promiscuous compounds:   0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.645 MDCK Permeability:   -4.636
Pgp-inhibitor:   0.136 Pgp-substrate:   0.031
PAMPA:   0.792
?
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):   0.462
20% Bioavailability (F20%):   0.678 30% Bioavailability (F30%):   0.847
50% Bioavailability (F50%):   0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.095 MRP1:   0.909
Plasma Protein Binding (PPB):   67.017% Volume Distribution (VD):   0.14
Fu: 32.262%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.992
OATP1B3 inhibitor:   0.972 BCRP inhibitor:   0.14
BSEP inhibitor:   0.07

ADMET: Metabolism

CYP1A2-inhibitor:   0.16 CYP1A2-substrate:   0.943
CYP2C19-inhibitor:   0.997 CYP2C19-substrate:   0.438
CYP2C9-inhibitor:   0.061 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.001 CYP2D6-substrate:   0.354
CYP3A4-inhibitor:   0.016 CYP3A4-substrate:   0.105
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.999
HLM stability:   1.0
?
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):  11.143 Half-life (T1/2):  1.141

ADMET: Toxicity

hERG Blockers:  0.005 hERG Blockers (10um):  0.089
Human Hepatotoxicity (H-HT):  0.714 Drug-induced Liver Injury (DILI):  0.294
AMES Toxicity:  0.51 Rat Oral Acute Toxicity:  0.93
Maximum Recommended Daily Dose:  0.074 Skin Sensitization:  0.696
Carcinogencity:  0.375 Eye Corrosion:  0.0
Eye Irritation:  0.112 Respiratory Toxicity:  0.882
Drug-induced Neurotoxicity:  0.283 Ototoxicity:  0.822
Hematotoxicity:  0.582 Drug-induced Nephrotoxicity:  0.941
Genotoxicity:  0.976 RPMI-8226 Immunitoxicity:  0.015
A549 Cytotoxicity:  0.093 Hek293 Cytotoxicity:  0.075
BCF:   1.799
?
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:   4.414
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.933
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.566
?
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
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1007/s11746-010-1670-2]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.foodcont.2016.09.002]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.jfca.2010.08.006]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2010.06.003]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2010.12.007]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2016.02.010]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2018.06.017]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.12691/jfnr-2-5-9]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[15217296]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[16499319]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. Mongolian n.a. PMID[17542634]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast 2003-JUN PMID[18298079]
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]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[18942825]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[19628108]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[20405844]
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]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[22538527]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[24811150]
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]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[28274428]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30236698]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[30384263]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds Guangzhou, China PMID[30563201]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30583361]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30599958]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[31159190]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[31861466]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36613240]
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]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13030 Artemisia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21830 Buddleja cordata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12196 Buphane fischeri n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO5930 Crambe tatarica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12700 Diospyros eriantha Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO252 Hoffmannia strigillosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11848 Lemaireocereus griseus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9934 Mycobacterium leprae Species Mycobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13671 Ononis vaginalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14578 Prorocentrum micans Species Prorocentraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8928 Pteris semipinnata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13585 Rapanea lancifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10783 Syncarpia hillii Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6360 Xenoacremonium recifei Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8928 Pteris semipinnata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9934 Mycobacterium leprae Species Mycobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10783 Syncarpia hillii Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13585 Rapanea lancifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13030 Artemisia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21830 Buddleja cordata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12700 Diospyros eriantha Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6360 Xenoacremonium recifei Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11848 Lemaireocereus griseus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO252 Hoffmannia strigillosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14578 Prorocentrum micans Species Prorocentraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5930 Crambe tatarica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12196 Buphane fischeri n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13671 Ononis vaginalis Species Fabaceae 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
NPT113 Cell line RAW264.7 Mus musculus IC50 > 100000.0 nM PMID[15679315]
NPT113 Cell line RAW264.7 Mus musculus Activity > 95.0 % PMID[15679315]

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 NPC38455 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
NPC

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC38455 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