NPASS Compound

Natural Product: NPC471881

Natural Product ID	NPC471881
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-P-O-Coumaroyl-1,4,6'-O-Triacetyl Sucrose
IUPAC Name	[(2S,3S,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3262769
PubChem CID	90676539
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

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 77 79 0 0 0 0 0 0 0 0999 V2000 1.1911 -5.0685 -1.7604 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8533 -4.1538 -0.9424 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 -3.6462 0.1436 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4762 -2.7544 0.9905 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7951 -1.5439 0.9479 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5690 -1.9109 0.4763 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3307 -3.0355 -0.4559 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4112 -3.9373 -0.3475 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0979 -4.4837 -1.3922 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7562 -4.1707 -2.5609 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2133 -5.4192 -1.0936 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4074 -0.8893 0.0820 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6058 -0.5446 0.6778 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9660 -1.2178 1.6600 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4626 0.5435 0.2336 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1685 1.3171 -0.7950 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9911 2.4135 -1.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5749 3.1547 -2.3641 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3191 4.2072 -2.8573 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5177 4.5678 -2.2815 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9475 3.8344 -1.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1903 2.7956 -0.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2570 5.6299 -2.7881 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7357 -1.0340 2.3663 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0845 -1.8174 3.2940 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3552 -3.0521 3.7675 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3626 -3.6589 3.3450 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4980 -3.7398 4.7829 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5329 -0.7228 0.1254 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1086 0.5401 -0.1002 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9845 1.4964 0.5270 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2584 1.1100 0.1396 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2393 1.8200 1.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0891 3.2166 0.9053 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8828 4.0903 1.6356 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7379 3.6056 2.4186 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7144 5.5548 1.4858 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4214 1.6103 -1.2838 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3580 1.1362 -2.2005 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0335 0.8369 -1.5654 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4994 -0.2536 -2.2391 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1699 2.0946 -3.2002 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6869 1.2547 -1.7888 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7895 -5.8172 -1.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1227 -3.2902 -1.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7848 -4.5683 -0.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6100 -4.5407 0.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0760 -2.3794 1.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0698 -2.7929 -1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1901 -4.8570 -1.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1249 -5.8067 -0.0667 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3052 -6.2237 -1.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3828 0.7486 0.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2370 1.0939 -1.2994 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6440 2.9074 -2.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9832 4.7813 -3.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8981 4.1369 -0.7498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5744 2.2580 0.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7900 6.1678 -2.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7205 -0.6434 2.7111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1173 -0.0836 2.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1116 -4.3673 5.4485 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1686 -4.4317 4.2011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0482 -3.0284 5.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1360 0.8257 0.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 0.0202 0.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9658 1.5687 2.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2907 1.5218 0.8407 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7127 5.8285 1.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8964 6.0173 2.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4870 5.8974 0.7650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4064 2.7253 -1.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7593 0.2225 -2.7299 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3240 1.6938 -1.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9087 -0.3494 -3.1363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.9923 -2.9488 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3327 1.9965 -1.7007 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 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 5 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 5 29 1 6 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 32 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 7 3 1 0 22 17 1 0 40 30 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 1 6 48 1 1 7 49 1 6 11 50 1 0 11 51 1 0 11 52 1 0 15 53 1 0 16 54 1 0 18 55 1 0 19 56 1 0 21 57 1 0 22 58 1 0 23 59 1 0 24 60 1 0 24 61 1 0 28 62 1 0 28 63 1 0 28 64 1 0 30 65 1 1 32 66 1 6 33 67 1 0 33 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 38 72 1 1 39 73 1 6 40 74 1 1 41 75 1 0 42 76 1 0 43 77 1 0 M END

Standard InCHIKey	JKZKIQWFVBPCHT-BTUCETIBSA-N
Standard InCHI	InChI=1S/C27H34O16/c1-13(29)37-11-19-21(34)22(35)23(36)26(40-19)43-27(12-38-14(2)30)25(24(39-15(3)31)18(10-28)42-27)41-20(33)9-6-16-4-7-17(32)8-5-16/h4-9,18-19,21-26,28,32,34-36H,10-12H2,1-3H3/b9-6+/t18-,19-,21-,22+,23-,24-,25+,26-,27+/m1/s1
SMILES	OC[C@H]1O[C@@]([C@H]([C@@H]1OC(=O)C)OC(=O)/C=C/c1ccc(cc1)O)(COC(=O)C)O[C@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	614.18	Volume:	569.431 ? Van der Waals volume.
Dense:	1.079	LogP:	-0.046 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.604 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	22.0
TPSA:	234.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.769	Fsp³:	0.556
MCE-18:	89.143 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.866	Fluc inhibitor:	0.563 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.192 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.338 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.114	Promiscuous compounds:	0.587

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.003	MDCK Permeability:	-5.184
Pgp-inhibitor:	0.002	Pgp-substrate:	0.602
PAMPA:	0.997 ? 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):	0.815
20% Bioavailability (F20%):	0.984	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.091
Plasma Protein Binding (PPB):	48.935%	Volume Distribution (VD):	-0.487
Fu:	51.19% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.002
BSEP inhibitor:	0.067

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.247
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.29 ? 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):

1.199

Half-life (T1/2):

1.897

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.918
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.019	Skin Sensitization:	1.0
Carcinogencity:	0.315	Eye Corrosion:	0.0
Eye Irritation:	0.083	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.109	Ototoxicity:	0.824
Hematotoxicity:	0.515	Drug-induced Nephrotoxicity:	0.871
Genotoxicity:	0.925	RPMI-8226 Immunitoxicity:	0.203
A549 Cytotoxicity:	0.553	Hek293 Cytotoxicity:	0.512
BCF:	0.484 ? 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:	3.167 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.644 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.156 ? 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
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[18449498]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24767839]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27241	Prunus tomentosa	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
IC50	4

Activity Type	# Activity
Cell line	4

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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	620.0	nM	PMID[23434030]
NPT81	Cell line	A549	Homo sapiens	IC50	=	290.0	nM	PMID[25479041]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	110.0	nM	DrugMatrix in vivo data: Pathology
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	180.0	nM	PubChem BioAssay data set

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 NPC471881 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	11450
0.1-0.2	33264
0.2-0.3	4402
0.3-0.4	603
0.4-0.5	104
0.5-0.6	24
0.6-0.7	7
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
0.6522	Remote Similarity	NPC28651
0.6506	Remote Similarity	NPC28637
0.6484	Remote Similarity	NPC201148
0.631	Remote Similarity	NPC35288
0.6154	Remote Similarity	NPC125823
0.6154	Remote Similarity	NPC7145
0.6154	Remote Similarity	NPC143480
0.5977	Remote Similarity	NPC471882
0.593	Remote Similarity	NPC45224
0.5882	Remote Similarity	NPC225307
0.5851	Remote Similarity	NPC472611
0.5778	Remote Similarity	NPC289967
0.5745	Remote Similarity	NPC3460
0.5591	Remote Similarity	NPC300262
0.5488	Remote Similarity	NPC479473
0.5488	Remote Similarity	NPC275721
0.5488	Remote Similarity	NPC288416
0.5488	Remote Similarity	NPC479468
0.5488	Remote Similarity	NPC479474
0.5465	Remote Similarity	NPC219677
0.5455	Remote Similarity	NPC281798
0.5281	Remote Similarity	NPC156692
0.5275	Remote Similarity	NPC173150
0.5233	Remote Similarity	NPC34293
0.5222	Remote Similarity	NPC471883
0.5213	Remote Similarity	NPC83743
0.5132	Remote Similarity	NPC11724
0.5114	Remote Similarity	NPC252114
0.5109	Remote Similarity	NPC226005
0.5062	Remote Similarity	NPC52097
0.5051	Remote Similarity	NPC215095

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4728
0.1-0.2	4332
0.2-0.3	88
0.3-0.4	1
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