NPASS Compound

Natural Product: NPC472714

Natural Product ID	NPC472714
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MGUZEJUQIKUKHQ-NPUIBITLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581700
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

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 80 82 0 0 0 0 0 0 0 0999 V2000 1.0154 -1.2597 3.0764 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2340 -1.6419 1.7308 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3574 -0.7446 0.8877 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0756 -0.8661 1.1995 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7335 -2.1920 1.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7312 -2.8452 -0.2337 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8244 -3.8179 -0.5983 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8360 -4.4090 -1.8377 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1095 -5.3773 -2.1213 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0708 -5.7682 -1.1810 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7716 -4.0454 -2.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6910 -3.0849 -2.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6644 -2.5065 -1.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6419 -2.6937 -3.3725 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 -1.7298 -3.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7363 -4.6785 -4.0218 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9152 0.2165 0.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5955 1.4847 0.8532 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7496 1.8719 2.1636 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8045 2.8405 2.1415 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4593 3.7610 1.1591 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6784 4.5380 0.6861 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4148 4.7050 1.7287 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7832 4.0448 2.9192 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5137 2.5671 2.6577 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0804 2.0444 3.8754 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5970 4.1958 4.0504 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4969 4.9956 0.7333 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6993 -0.6535 -0.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0882 -0.1274 -0.7675 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3400 1.2216 -0.9075 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6074 1.7261 -1.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8746 3.0845 -1.2555 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7566 3.9556 -1.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6414 0.8121 -1.1745 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4648 -0.5550 -1.0425 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1663 -0.9808 -0.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5442 -1.4499 -1.1116 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2497 -2.8255 -0.9664 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9380 1.2900 -1.3812 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1621 -0.2813 3.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0891 -2.7072 1.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3172 -1.4330 1.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6625 0.3102 1.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1772 -0.5900 2.3043 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3468 -2.9442 1.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8290 -2.1128 1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0648 -4.1481 0.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6673 -6.5895 -1.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5294 -6.1161 -0.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7412 -4.9533 -0.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3993 -1.7336 -0.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0604 -1.7339 -2.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1896 -0.7279 -3.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4721 -1.8093 -3.8887 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8996 -4.8171 -4.5484 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9133 0.1211 -0.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9903 -0.0189 0.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0964 1.0790 2.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0118 3.2563 0.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5827 3.9527 0.8887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6922 5.5462 1.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5872 4.6834 -0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9341 5.6414 2.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1907 4.5155 3.1431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3373 2.5438 1.9502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8891 2.0642 3.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0583 5.0625 4.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 5.3126 -0.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0431 0.1376 -1.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6184 -1.5308 -1.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5354 1.9409 -0.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2291 3.7974 -0.1954 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9868 3.6739 -1.9476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9978 5.0056 -1.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9704 -2.0613 -0.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4142 -3.1416 -1.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1196 -3.4578 -1.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9575 -3.1108 0.0429 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1114 2.2722 -1.5555 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 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 8 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 11 16 1 0 4 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 3 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 35 40 1 0 13 6 1 0 25 19 1 0 37 30 1 0 1 41 1 0 2 42 1 0 2 43 1 0 3 44 1 1 4 45 1 1 5 46 1 0 5 47 1 0 7 48 1 0 10 49 1 0 10 50 1 0 10 51 1 0 13 52 1 0 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 19 59 1 1 21 60 1 6 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 1 24 65 1 1 25 66 1 6 26 67 1 0 27 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 31 72 1 0 34 73 1 0 34 74 1 0 34 75 1 0 37 76 1 0 39 77 1 0 39 78 1 0 39 79 1 0 40 80 1 0 M END

Standard InCHIKey	MGUZEJUQIKUKHQ-NPUIBITLSA-N
Standard InCHI	InChI=1S/C28H40O12/c1-14-23(30)26(33)27(34)28(40-14)39-13-18(7-16-10-21(37-4)25(32)22(11-16)38-5)17(12-29)6-15-8-19(35-2)24(31)20(9-15)36-3/h8-11,14,17-18,23,26-34H,6-7,12-13H2,1-5H3/t14-,17+,18+,23-,26+,27+,28+/m0/s1
SMILES	OC[C@H]([C@H](Cc1cc(OC)c(c(c1)OC)O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)Cc1cc(OC)c(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.25	Volume:	556.839 ? Van der Waals volume.
Dense:	1.02	LogP:	0.753 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.237 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.306 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	18.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.202	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.332	Fsp³:	0.571
MCE-18:	77.455 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.388	Fluc inhibitor:	0.16 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.298 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.136	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.99	MDCK Permeability:	-5.265
Pgp-inhibitor:	0.578	Pgp-substrate:	0.898
PAMPA:	0.045 ? 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):	0.079
20% Bioavailability (F20%):	0.108	30% Bioavailability (F30%):	0.205
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.964
Plasma Protein Binding (PPB):	84.132%	Volume Distribution (VD):	-0.304
Fu:	18.086% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.799
BSEP inhibitor:	0.933

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.996	CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.237	CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.26 ? 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):

3.037

Half-life (T1/2):

3.208

ADMET: Toxicity

hERG Blockers:	0.066	hERG Blockers (10um):	0.356
Human Hepatotoxicity (H-HT):	0.454	Drug-induced Liver Injury (DILI):	0.484
AMES Toxicity:	0.409	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.042	Skin Sensitization:	0.889
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.027	Respiratory Toxicity:	0.067
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.959
Hematotoxicity:	0.338	Drug-induced Nephrotoxicity:	0.597
Genotoxicity:	0.017	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.288	Hek293 Cytotoxicity:	0.272
BCF:	0.84 ? 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:	3.622 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.047 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.291 ? 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
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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
Activity	1
IC50	5

Activity Type	# Activity
Cell line	5
Non-molecular	1

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
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	167.61	%	PMID[22934600]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[15165134]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[19015349]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	Open TG-GATES in vivo data: Hematology
NPT148	Cell line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[20624681]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	21300.0	nM	PMID[25894905]

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 NPC472714 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	12285
0.1-0.2	32012
0.2-0.3	5029
0.3-0.4	477
0.4-0.5	35
0.5-0.6	14
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8448	Intermediate Similarity	NPC5262
0.7121	Intermediate Similarity	NPC472713
0.6479	Remote Similarity	NPC225815
0.6479	Remote Similarity	NPC602887
0.6176	Remote Similarity	NPC473046
0.6143	Remote Similarity	NPC606627
0.597	Remote Similarity	NPC278961
0.597	Remote Similarity	NPC113680
0.5733	Remote Similarity	NPC472711
0.5676	Remote Similarity	NPC90208
0.5467	Remote Similarity	NPC185955
0.5467	Remote Similarity	NPC9933
0.5467	Remote Similarity	NPC145979
0.5467	Remote Similarity	NPC469706
0.5467	Remote Similarity	NPC218041
0.5467	Remote Similarity	NPC214326
0.5467	Remote Similarity	NPC260781
0.5417	Remote Similarity	NPC156376
0.5316	Remote Similarity	NPC286245
0.5139	Remote Similarity	NPC118385

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4225
0.1-0.2	4788
0.2-0.3	129
0.3-0.4	8
0.4-0.5	0
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