NPASS Compound

Natural Product: NPC488076

Natural Product ID	NPC488076
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AZGULWNCWHTTRE-WNBSLVDXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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 74 78 0 0 0 0 0 0 0 0999 V2000 6.9482 -0.3288 4.8789 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0818 0.7428 4.5684 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4931 0.7618 3.3090 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1783 1.4099 2.3063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6046 1.4341 1.0566 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3682 0.8204 0.8188 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7057 0.1782 1.8461 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2850 0.1562 3.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6006 -0.4943 4.1108 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4918 -0.4251 1.6281 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8728 -1.0137 2.5505 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9330 -0.3787 0.3351 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6355 0.2649 -0.6369 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1934 0.3911 -2.0119 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2095 -0.3558 -2.5610 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7883 -0.1415 -3.8944 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3706 0.8302 -4.6629 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3672 1.5852 -4.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7645 1.3622 -2.8056 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9581 2.5684 -4.8843 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9370 1.0279 -5.9884 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8135 0.8289 -0.3364 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6868 -1.0068 0.1814 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5059 -0.2623 0.4869 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5827 -0.5947 -0.4593 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7953 -2.1092 -0.2902 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3952 -2.2148 1.1130 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6623 -1.4719 2.1535 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9745 -2.4854 3.0821 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8805 -3.4831 3.4076 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8536 -0.4501 1.8159 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5876 -3.5329 1.4405 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5680 -2.7676 -0.2699 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8248 -0.0505 -0.0116 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4055 0.7102 -1.0011 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7531 0.2511 -1.4483 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4177 1.5916 -1.7759 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9022 1.5217 -1.6712 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3541 1.0556 -0.4536 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7913 2.4406 -0.6635 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 2.0109 -0.5773 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0288 2.0584 -3.0070 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6773 -0.5203 -2.5993 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4159 2.0233 2.5481 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5171 -0.5783 3.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4347 -1.2368 5.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6681 0.0674 5.6389 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1207 1.9380 0.2418 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0822 -1.1018 4.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7470 -1.1431 -2.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0009 -0.7584 -4.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 1.9825 -2.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3760 3.0807 -5.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4034 0.5244 -6.7372 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2275 0.8047 0.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3845 -0.2898 -1.4745 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4994 -2.5151 -1.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4199 -1.7450 0.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4479 -1.0158 2.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6805 -1.9976 4.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1103 -2.9658 2.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4021 -4.2258 3.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5174 -3.6896 1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6483 -3.5561 -0.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7383 0.7001 -1.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2893 -0.2631 -0.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2792 2.5759 -1.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2841 0.9773 -2.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5376 0.0815 -0.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9253 3.4840 -0.9544 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3962 2.1826 0.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1969 2.5950 -2.9336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2385 -0.1006 -3.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0508 2.2506 1.8051 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 7 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 13 22 1 0 12 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 37 42 1 6 36 43 1 0 4 44 1 0 8 3 1 0 19 14 1 0 31 24 1 0 41 35 1 0 22 6 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 0 9 49 1 0 15 50 1 0 16 51 1 0 19 52 1 0 20 53 1 0 21 54 1 0 24 55 1 1 25 56 1 6 26 57 1 6 27 58 1 6 28 59 1 1 29 60 1 0 29 61 1 0 30 62 1 0 32 63 1 0 33 64 1 0 35 65 1 6 36 66 1 1 38 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 40 71 1 0 42 72 1 0 43 73 1 0 44 74 1 0 M END

Standard InCHIKey	AZGULWNCWHTTRE-WNBSLVDXSA-N
Standard InCHI	InChI=1S/C27H30O17/c1-39-21-12(32)5-13-15(17(21)34)18(35)22(20(41-13)9-2-3-10(30)11(31)4-9)43-25-23(19(36)16(33)14(6-28)42-25)44-26-24(37)27(38,7-29)8-40-26/h2-5,14,16,19,23-26,28-34,36-38H,6-8H2,1H3/t14-,16+,19+,23-,24+,25+,26+,27-/m1/s1
SMILES	COc1c(cc2c(c1O)c(=O)c(c(c1ccc(c(c1)O)O)o2)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	626.15	Volume:	561.108 ? Van der Waals volume.
Dense:	1.116	LogP:	0.699 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.982 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.121 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	29.0
TPSA:	278.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.12	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.884	Fsp³:	0.444
MCE-18:	124.615 ? 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:	1
Colloidal aggregators:	0.613	Fluc inhibitor:	0.269 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.783 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.564 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.147	Promiscuous compounds:	0.576

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.358	MDCK Permeability:	-5.247
Pgp-inhibitor:	0.0	Pgp-substrate:	0.172
PAMPA:	0.994 ? 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):	0.967
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.878
Plasma Protein Binding (PPB):	77.733%	Volume Distribution (VD):	-0.16
Fu:	19.392% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.952
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.066
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.044	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.52
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.987
HLM stability:	0.856 ? 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):

2.274

Half-life (T1/2):

2.921

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.077
Human Hepatotoxicity (H-HT):	0.702	Drug-induced Liver Injury (DILI):	0.882
AMES Toxicity:	0.96	Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.092	Skin Sensitization:	1.0
Carcinogencity:	0.404	Eye Corrosion:	0.0
Eye Irritation:	0.724	Respiratory Toxicity:	0.047
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.942
Hematotoxicity:	0.221	Drug-induced Nephrotoxicity:	0.343
Genotoxicity:	0.943	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.986	Hek293 Cytotoxicity:	0.759
BCF:	0.37 ? 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:	2.885 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.488 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.665 ? 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
NPO40820	Corispermum marschallii	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[30109803]

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	3

Activity Type	# Activity
Cell line	3

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
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	7100.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	7200.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	12800.0	nM	PMID[30109803]

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 NPC488076 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	20601
0.1-0.2	26409
0.2-0.3	2153
0.3-0.4	385
0.4-0.5	237
0.5-0.6	53
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC480471
0.8242	Intermediate Similarity	NPC488075
0.7282	Intermediate Similarity	NPC480472
0.6774	Remote Similarity	NPC470444
0.6596	Remote Similarity	NPC255157
0.6596	Remote Similarity	NPC259896
0.6591	Remote Similarity	NPC42773
0.6591	Remote Similarity	NPC45522
0.6413	Remote Similarity	NPC254855
0.6413	Remote Similarity	NPC94610
0.6354	Remote Similarity	NPC488073
0.6311	Remote Similarity	NPC303694
0.6146	Remote Similarity	NPC155877
0.5979	Remote Similarity	NPC304741
0.5934	Remote Similarity	NPC305811
0.5929	Remote Similarity	NPC480470
0.5859	Remote Similarity	NPC488074
0.5833	Remote Similarity	NPC473682
0.5789	Remote Similarity	NPC170052
0.5789	Remote Similarity	NPC135846
0.5784	Remote Similarity	NPC473071
0.5761	Remote Similarity	NPC488080
0.5761	Remote Similarity	NPC169977
0.5758	Remote Similarity	NPC122809
0.57	Remote Similarity	NPC126784
0.57	Remote Similarity	NPC241423
0.5631	Remote Similarity	NPC220173
0.5625	Remote Similarity	NPC163524
0.5579	Remote Similarity	NPC101026
0.5579	Remote Similarity	NPC488077
0.5579	Remote Similarity	NPC224530
0.5577	Remote Similarity	NPC470445
0.5556	Remote Similarity	NPC163242
0.5556	Remote Similarity	NPC272068
0.5545	Remote Similarity	NPC253521
0.5545	Remote Similarity	NPC113836
0.5517	Remote Similarity	NPC21359
0.5517	Remote Similarity	NPC460984
0.5463	Remote Similarity	NPC219043
0.5408	Remote Similarity	NPC95866
0.5392	Remote Similarity	NPC240306
0.5377	Remote Similarity	NPC470446
0.5333	Remote Similarity	NPC76831
0.5321	Remote Similarity	NPC48984
0.5312	Remote Similarity	NPC488071
0.5288	Remote Similarity	NPC122467
0.5283	Remote Similarity	NPC292929
0.5248	Remote Similarity	NPC470405
0.5229	Remote Similarity	NPC473072
0.5229	Remote Similarity	NPC470451
0.5161	Remote Similarity	NPC67037
0.5161	Remote Similarity	NPC255615
0.5158	Remote Similarity	NPC145038
0.5158	Remote Similarity	NPC56077
0.5158	Remote Similarity	NPC281131
0.5158	Remote Similarity	NPC253662
0.5158	Remote Similarity	NPC179950
0.5158	Remote Similarity	NPC88789
0.5158	Remote Similarity	NPC491374
0.5135	Remote Similarity	NPC480441
0.5096	Remote Similarity	NPC61904
0.5094	Remote Similarity	NPC472991
0.5093	Remote Similarity	NPC602448
0.5049	Remote Similarity	NPC156869
0.5046	Remote Similarity	NPC14187
0.5042	Remote Similarity	NPC25946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5622
0.1-0.2	3496
0.2-0.3	26
0.3-0.4	4
0.4-0.5	2
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