NPASS Compound

Natural Product: NPC132680

Natural Product ID	NPC132680
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pyridoxine Hydrochloride
IUPAC Name	4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol;hydrochloride
Synonyms	Beesix; Benadon; Comploment Continus; Hexa-Betalin; Kent B6; Lyphomed; Orovite Comploment B6; Pyrid-10; Pyrid-20; Pyridox HCl; Pyridox-Roche; Pyridoxine HCl; Pyridoxol Hcl; Vital Foods; Vitalife; Vitamin B6
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1200756
PubChem CID	6019 51064122 517312 88396073
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001948] Pyridoxines

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

Chemical Representations

RDKit 3D 25 24 0 0 0 0 0 0 0 0999 V2000 2.7160 0.4338 -1.9382 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6334 0.5549 -0.9275 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6233 -0.3978 -0.8638 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4090 -0.3178 0.0725 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4897 -1.3167 0.1826 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0506 -2.4515 0.8585 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3701 0.7584 0.9297 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6161 1.7136 0.8883 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5756 1.5614 -0.0462 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4506 0.8484 1.9424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6495 1.2904 1.3934 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6070 -1.4589 -1.7259 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6832 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.9776 1.4517 -2.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6501 0.0088 -1.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3881 -0.1541 -2.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3989 -0.9386 0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8400 -1.6162 -0.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0877 -3.2484 0.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6018 2.5408 1.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1104 1.5685 2.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6516 -0.1579 2.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5699 1.7347 0.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6893 -2.4076 -1.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6832 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 4 7 2 0 7 8 1 0 8 9 2 0 7 10 1 0 10 11 1 0 3 12 1 0 9 2 1 0 1 14 1 0 1 15 1 0 1 16 1 0 5 17 1 0 5 18 1 0 6 19 1 0 8 20 1 0 10 21 1 0 10 22 1 0 11 23 1 0 12 24 1 0 13 25 1 0 M END

Standard InCHIKey	ZUFQODAHGAHPFQ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C8H11NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,10-12H,3-4H2,1H3;1H
SMILES	Cc1c(c(CO)c(cn1)CO)O.Cl

Calculated Properties

Physi-Chem Properties

Molecular Weight:	169.07	Volume:	167.826 ? Van der Waals volume.
Dense:	1.007	LogP:	-0.654 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.179 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.478 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	6.0
TPSA:	73.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	1.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.586	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.549	Fsp³:	0.375
MCE-18:	7.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.013	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.046 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.038 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.228	Promiscuous compounds:	0.221

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.986	MDCK Permeability:	-4.78
Pgp-inhibitor:	0.0	Pgp-substrate:	0.039
PAMPA:	0.969 ? 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):	0.034
20% Bioavailability (F20%):	0.075	30% Bioavailability (F30%):	0.192
50% Bioavailability (F50%):	0.272

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03	MRP1:	0.952
Plasma Protein Binding (PPB):	9.849%	Volume Distribution (VD):	-0.174
Fu:	90.118% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.887
OATP1B3 inhibitor:	0.935	BCRP inhibitor:	0.004
BSEP inhibitor:	0.028

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.106	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.907	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.946	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.027
HLM stability:	0.0 ? 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):

7.347

Half-life (T1/2):

1.311

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.233
Human Hepatotoxicity (H-HT):	0.405	Drug-induced Liver Injury (DILI):	0.042
AMES Toxicity:	0.431	Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.174	Skin Sensitization:	0.712
Carcinogencity:	0.694	Eye Corrosion:	0.097
Eye Irritation:	0.972	Respiratory Toxicity:	0.426
Drug-induced Neurotoxicity:	0.211	Ototoxicity:	0.342
Hematotoxicity:	0.12	Drug-induced Nephrotoxicity:	0.197
Genotoxicity:	0.559	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.018	Hek293 Cytotoxicity:	0.091
BCF:	0.13 ? 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:	1.814 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.247 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.362 ? 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
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2020.113007]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-1656(02)00067-6]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3923/pjbs.2013.1138.1144]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17262437]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18326559]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Essential oil	n.a.	n.a.	PMID[23163425]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23865201]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[24508058]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	garlic skin	n.a.	n.a.	PMID[25726329]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37241721]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350088]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	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

Activity Type	# Activity
Potency	11
Inhibition	4
Ki	4
Inhibition index	1

Activity Type	# Activity
Individual protein	6
Organism	4
Single protein	1
Others	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PubChem BioAssay data set
NPT7	Individual protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	10.52	%	DOI[10.6019/CHEMBL4495564]
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	100000.0	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	1062.1	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition index	=	0.1746	n.a.	DOI[10.1101/2020.04.03.023846]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	4.95	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.25	%	DOI[10.6019/CHEMBL4495565]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13685.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24544.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1096.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Ki	=	8290000.0	nM	PMID[21944860]
NPT2	Others	Unspecified	n.a.	Ki	=	8670000.0	nM	PMID[21944860]
NPT2	Others	Unspecified	n.a.	Ki	=	5560000.0	nM	PMID[21944860]
NPT2	Others	Unspecified	n.a.	Ki	=	5050000.0	nM	PMID[21944860]

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
-	Rattus norvegicus	LEL	=	12160.0	mg/kg-day	ToxVal
-	Rattus norvegicus	LEL	=	4940.0	mg/kg-day	ToxVal
-	Rattus norvegicus	LD50	=	7750.0	mg/kg	ToxVal
-	Rattus norvegicus	LD50	=	4000.0	mg/kg	ToxVal
-	Mus musculus	LD0	=	3344.0	mg/kg	ToxVal
-	Mus musculus	LD50	>=	6994.0	mg/kg	ToxVal
-	Mus musculus	LD50	=	5500.0	mg/kg	ToxVal
-	Homo sapiens	DNEL systemic	=	1.9	mg/m3	ToxVal

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

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 NPC132680 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	38149
0.1-0.2	11547
0.2-0.3	147
0.3-0.4	7
0.4-0.5	0
0.5-0.6	1
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC269919
0.7097	Intermediate Similarity	NPC63562
0.6765	Remote Similarity	NPC322976
0.6765	Remote Similarity	NPC324203
0.6571	Remote Similarity	NPC325705
0.6471	Remote Similarity	NPC63338
0.6286	Remote Similarity	NPC52831
0.5789	Remote Similarity	NPC263439

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC132680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6807
0.1-0.2	2307
0.2-0.3	28
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9382	Approved
0.963	High Similarity	NPD9383	Phase 4
0.6471	Remote Similarity	NPD9398	Phase 2
0.6286	Remote Similarity	NPD9510	Phase 3
0.5789	Remote Similarity	NPD2123	Phase 3

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