NPASS Compound

Natural Product: NPC103344

Natural Product ID	NPC103344
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BOFOQQHNACWIOH-RHAOSNMYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46830349
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 63 64 0 0 0 0 0 0 0 0999 V2000 10.6781 0.0524 1.8605 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7251 0.1861 0.7567 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8833 1.4712 0.6578 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8507 1.1221 -0.1688 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6759 0.7141 -1.0805 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7894 0.3970 -1.7488 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8960 0.0823 -2.4028 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8201 -0.3126 -3.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8166 -0.8066 -1.9544 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0356 -0.1895 -1.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7681 0.3308 -0.9662 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2723 -0.5521 -1.3239 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4947 -1.6980 -0.2998 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8859 -2.1990 -0.7232 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7598 -1.0976 -0.0605 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4896 0.1311 -0.9126 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3979 1.3064 0.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5263 1.3994 0.7647 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6318 2.0285 0.4357 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9126 1.2343 0.1644 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7480 1.4065 1.3989 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3723 0.1053 1.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4778 -0.9331 1.9655 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6892 1.8822 2.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0132 2.8281 1.5774 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7433 2.3783 1.3439 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6205 1.7936 -0.9253 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4079 -0.1070 -1.7322 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9949 -1.5066 0.2450 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1714 -3.4661 -0.2618 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4202 -2.7633 -0.5259 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4326 0.6669 2.7766 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5257 -1.0577 2.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7706 0.2086 1.6556 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1617 -0.7147 0.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4718 0.3747 -0.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5442 2.2429 0.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6939 1.9446 1.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1834 0.6150 -3.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7793 -1.1013 -3.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6470 -1.9023 -2.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8071 -1.0412 -1.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6566 0.8223 -0.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1514 -0.7578 0.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2742 -1.2158 -2.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4457 -1.4468 0.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0411 -2.0103 -1.8080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2012 -0.8670 0.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3866 0.3117 -1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4434 1.2886 0.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3455 2.1944 -0.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5344 2.6752 -0.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7140 0.1866 -0.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2203 -0.1332 1.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7667 0.2902 2.8768 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5153 -1.4596 1.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0341 1.0130 2.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1645 2.3809 3.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3764 3.2373 1.8037 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2532 2.6955 -1.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0754 -1.5791 1.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9482 -3.7890 -0.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6168 -2.6936 -1.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 3 0 5 6 1 0 6 7 3 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 21 26 1 6 20 27 1 0 16 28 1 0 15 29 1 0 14 30 1 0 13 31 1 0 28 12 1 0 25 19 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 2 36 1 0 3 37 1 0 3 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 12 45 1 6 13 46 1 1 14 47 1 6 15 48 1 1 16 49 1 6 17 50 1 0 17 51 1 0 19 52 1 6 20 53 1 6 22 54 1 0 22 55 1 0 23 56 1 0 24 57 1 0 24 58 1 0 26 59 1 0 27 60 1 0 29 61 1 0 30 62 1 0 31 63 1 0 M END

Standard InCHIKey	BOFOQQHNACWIOH-RHAOSNMYSA-N
Standard InCHI	InChI=1S/C21H32O10/c1-2-3-4-5-6-7-8-9-10-28-19-17(25)16(24)15(23)14(31-19)11-29-20-18(26)21(27,12-22)13-30-20/h14-20,22-27H,2-3,8-13H2,1H3/t14-,15-,16+,17-,18+,19-,20-,21-/m1/s1
SMILES	CCCC#CC#CCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@](CO)(CO2)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	444.2	Volume:	432.016 ? Van der Waals volume.
Dense:	1.028	LogP:	1.326 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.684 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.03 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	13.0
TPSA:	158.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	2.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.898	Fsp³:	0.81
MCE-18:	39.579 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.154	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.319	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.342	MDCK Permeability:	-4.927
Pgp-inhibitor:	0.002	Pgp-substrate:	0.001
PAMPA:	1.0 ? 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):	0.024
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.015
50% Bioavailability (F50%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	91.417%	Volume Distribution (VD):	-0.011
Fu:	7.169% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.036
OATP1B3 inhibitor:	0.116	BCRP inhibitor:	0.994
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.991
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.051
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

2.238

Half-life (T1/2):

1.898

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.138
Human Hepatotoxicity (H-HT):	0.612	Drug-induced Liver Injury (DILI):	0.711
AMES Toxicity:	0.923	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	0.999
Carcinogencity:	0.274	Eye Corrosion:	0.007
Eye Irritation:	0.574	Respiratory Toxicity:	0.337
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.923
Hematotoxicity:	0.086	Drug-induced Nephrotoxicity:	0.421
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.151
A549 Cytotoxicity:	0.221	Hek293 Cytotoxicity:	0.615
BCF:	0.508 ? 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:	3.146 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.682 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.81 ? 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
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	San Salvador in the Bahamas (12-26 m depth)	2001-MAR; 2003-JUL	PMID[17309298]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO2684	Cortinarius vinosipes	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4385	Aconitum zuccarini	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11166	Sclerodoris tanya	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11758	Parmelia pokornyi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11166	Sclerodoris tanya	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14222	Schefflera divaricata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4385	Aconitum zuccarini	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13119	Hymenoxys microcephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14310	Tecoma heptaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2684	Cortinarius vinosipes	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11402	Tithonia rotundifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14637	Saussurea cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390	Juniperus rigida	Species	Cupressaceae	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

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 NPC103344 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	25980
0.1-0.2	20630
0.2-0.3	2924
0.3-0.4	257
0.4-0.5	50
0.5-0.6	15
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	0

Similarity Score	Similarity Level	Natural Product ID
0.6731	Remote Similarity	NPC219040
0.6491	Remote Similarity	NPC472026
0.5362	Remote Similarity	NPC256230
0.5345	Remote Similarity	NPC147292
0.5312	Remote Similarity	NPC264784
0.5254	Remote Similarity	NPC277570
0.5217	Remote Similarity	NPC150463
0.5211	Remote Similarity	NPC249408
0.5143	Remote Similarity	NPC476448
0.5143	Remote Similarity	NPC469548
0.5143	Remote Similarity	NPC476445
0.5139	Remote Similarity	NPC104129
0.5135	Remote Similarity	NPC118078
0.5132	Remote Similarity	NPC239961
0.5102	Remote Similarity	NPC323574
0.5094	Remote Similarity	NPC233726
0.5082	Remote Similarity	NPC601155

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC103344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7426
0.1-0.2	1652
0.2-0.3	68
0.3-0.4	3
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

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