NPASS Compound

Natural Product: NPC318335

Natural Product ID	NPC318335
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YJGVMLPVUAXIQN-LLBQBPMSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5289185
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones [CHEMONTID:0000047] Podophyllotoxins

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 52 56 0 0 0 0 0 0 0 0999 V2000 2.2114 -0.3651 3.5638 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0889 -0.1002 2.4947 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6204 -0.2034 1.2027 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3119 -0.5614 0.9880 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7811 -0.6823 -0.2826 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6245 -0.4266 -1.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9379 -0.0662 -1.1925 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4211 0.0412 0.0943 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7316 0.3994 0.3228 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1701 1.7344 0.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7724 0.1870 -2.2713 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2948 0.0818 -3.6003 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0723 -0.4821 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0684 -2.1386 0.4553 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2469 -1.7753 1.3201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7496 -3.1459 1.7417 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5543 -3.9327 0.5614 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5767 -3.3577 -0.2365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2069 -3.8138 -1.3484 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3584 -1.1283 0.5268 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8129 0.1300 -0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5861 1.2570 -0.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1095 2.4237 -0.5976 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8133 2.4358 -1.0742 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0231 1.2846 -1.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5213 0.1177 -0.5065 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6068 3.7348 -1.5275 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6224 4.5855 -0.9962 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6835 3.6816 -0.7540 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7313 -2.0171 -0.5006 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6540 -0.1411 4.5492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2916 0.2774 3.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8428 -1.4145 3.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6805 -0.7536 1.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2298 -0.5152 -2.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4356 1.9647 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4404 2.4707 0.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1230 1.8678 -0.1004 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7198 0.9723 -3.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1333 -0.0087 -4.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6923 -0.8519 -3.7412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6804 -1.5096 -1.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2450 -2.4415 1.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9845 -1.1295 2.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8395 -3.0695 1.9595 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1520 -3.5077 2.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 -0.9528 1.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5863 1.2291 0.2890 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0246 1.4029 -1.4267 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8547 5.3128 -1.8001 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2907 5.1249 -0.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4441 -1.6346 -1.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 7 11 1 0 11 12 1 0 5 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 2 0 15 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 28 29 1 0 20 30 1 0 8 3 1 0 26 13 1 0 18 14 1 0 26 21 1 0 29 23 1 0 1 31 1 0 1 32 1 0 1 33 1 0 4 34 1 0 6 35 1 0 10 36 1 0 10 37 1 0 10 38 1 0 12 39 1 0 12 40 1 0 12 41 1 0 13 42 1 0 14 43 1 0 15 44 1 0 16 45 1 0 16 46 1 0 20 47 1 0 22 48 1 0 25 49 1 0 28 50 1 0 28 51 1 0 30 52 1 0 M END

Standard InCHIKey	YJGVMLPVUAXIQN-LLBQBPMSSA-N
Standard InCHI	InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19?,20-/m0/s1
SMILES	COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	414.13	Volume:	398.152 ? Van der Waals volume.
Dense:	1.04	LogP:	1.847 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.177 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.986 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	26.0
TPSA:	92.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.763	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.752	Fsp³:	0.409
MCE-18:	94.839 ? 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:	0.044	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.105 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.348 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.043	Promiscuous compounds:	0.289

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957	MDCK Permeability:	-4.744
Pgp-inhibitor:	0.037	Pgp-substrate:	0.001
PAMPA:	0.082 ? 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):	0.0
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.904	MRP1:	0.999
Plasma Protein Binding (PPB):	98.152%	Volume Distribution (VD):	-0.205
Fu:	3.012% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.454
OATP1B3 inhibitor:	0.85	BCRP inhibitor:	0.001
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.995	CYP2C19-substrate:	0.995
CYP2C9-inhibitor:	0.019	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.996
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.915
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.213
HLM stability:	0.152 ? 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):

3.551

Half-life (T1/2):

2.944

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.625
Human Hepatotoxicity (H-HT):	0.711	Drug-induced Liver Injury (DILI):	0.931
AMES Toxicity:	0.431	Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.744	Skin Sensitization:	0.399
Carcinogencity:	0.83	Eye Corrosion:	0.001
Eye Irritation:	0.29	Respiratory Toxicity:	0.462
Drug-induced Neurotoxicity:	0.759	Ototoxicity:	0.867
Hematotoxicity:	0.577	Drug-induced Nephrotoxicity:	0.884
Genotoxicity:	0.853	RPMI-8226 Immunitoxicity:	0.188
A549 Cytotoxicity:	0.233	Hek293 Cytotoxicity:	0.358
BCF:	1.144 ? 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:	3.52 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.829 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.436 ? 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
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933860]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[17256902]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	Roots	Panan, Zhejiang Province, China	2004-MAY	PMID[17256902]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25712646]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34203980]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37894884]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30053	Podophyllum emodll	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26868	Diphylleia sinensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20275	Juniperus sabina	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5200	Diphylleia grayi	Species	Berberidaceae	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 NPC318335 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	21331
0.1-0.2	26796
0.2-0.3	1501
0.3-0.4	157
0.4-0.5	42
0.5-0.6	15
0.6-0.7	9
0.7-0.8	1
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC237946
1.0	High Similarity	NPC32373
0.8947	High Similarity	NPC119910
0.8136	Intermediate Similarity	NPC91634
0.8136	Intermediate Similarity	NPC150943
0.8136	Intermediate Similarity	NPC268718
0.7667	Intermediate Similarity	NPC207584
0.7667	Intermediate Similarity	NPC19947
0.6885	Remote Similarity	NPC178574
0.6769	Remote Similarity	NPC288149
0.6557	Remote Similarity	NPC239890
0.6557	Remote Similarity	NPC209411
0.619	Remote Similarity	NPC80230
0.619	Remote Similarity	NPC104024
0.619	Remote Similarity	NPC101755
0.619	Remote Similarity	NPC304687
0.619	Remote Similarity	NPC65574
0.5846	Remote Similarity	NPC262455
0.5846	Remote Similarity	NPC177476
0.5821	Remote Similarity	NPC210642
0.5821	Remote Similarity	NPC13985
0.5758	Remote Similarity	NPC149505
0.5606	Remote Similarity	NPC65591
0.5571	Remote Similarity	NPC115281
0.5556	Remote Similarity	NPC477698
0.5522	Remote Similarity	NPC480477
0.5397	Remote Similarity	NPC164082
0.5246	Remote Similarity	NPC151423
0.5143	Remote Similarity	NPC30009
0.5143	Remote Similarity	NPC103197
0.5082	Remote Similarity	NPC218841
0.5062	Remote Similarity	NPC152424

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC318335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4679
0.1-0.2	4389
0.2-0.3	70
0.3-0.4	2
0.4-0.5	6
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4965	Approved
1.0	High Similarity	NPD4966	Phase 4
1.0	High Similarity	NPD4967	Phase 2
0.7429	Intermediate Similarity	NPD37	Approved

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