NPASS Compound

Natural Product: NPC475592

Natural Product ID	NPC475592
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Schizanrin J
IUPAC Name	n.a.
Synonyms	Schizanrin J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508847
PubChem CID	44583792
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 81 84 0 0 0 0 0 0 0 0999 V2000 -4.7671 -4.2865 -2.4031 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8712 -3.7439 -1.3564 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6423 -4.3138 -0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 -5.5818 0.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7413 -3.6749 0.7357 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4486 -4.1193 1.8707 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1510 -2.4894 0.3643 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2514 -1.7177 1.1226 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0742 -1.5603 0.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2359 -1.0737 1.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8831 0.1993 0.6912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9914 1.1568 0.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 1.8762 -0.8926 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0313 2.8174 -1.6768 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3365 3.0405 -1.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0684 2.3327 -0.6158 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3853 1.4171 0.1447 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4283 0.9122 1.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0628 2.0484 1.4728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1453 1.8711 2.3007 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5548 0.5813 2.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8846 -0.5077 2.2419 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 -0.3853 1.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6511 0.7540 3.5024 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0772 2.1177 3.4332 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9778 2.8237 2.8758 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5539 3.2535 1.0497 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5872 4.0061 1.7488 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4268 2.4441 -0.3977 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9992 3.9783 -2.3145 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1611 5.3265 -1.9438 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7059 3.5770 -2.6322 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0935 3.3573 -2.7796 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9359 -0.1352 -0.2099 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2584 0.1636 0.1019 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4967 0.7287 1.1683 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3515 -0.1753 -0.8008 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0565 -0.7956 -1.9352 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1366 -1.1632 -2.8876 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7525 0.1783 -0.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9992 -1.0006 2.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2761 -2.0554 1.0206 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3792 -2.9467 -0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2758 -5.0434 -3.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1402 -3.4328 -3.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7029 -4.7424 -2.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3768 -2.7893 -1.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0006 -5.5030 1.0069 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5614 -6.3770 0.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8702 -6.0214 -0.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0870 -2.2374 2.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0710 -0.9063 -0.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3554 0.6772 1.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7789 1.7253 -1.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1554 -1.5430 2.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2186 2.4672 4.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0069 2.2268 2.8542 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7795 5.0776 1.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4148 3.6868 1.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6742 3.7048 2.8235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1169 1.8132 -0.7797 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1747 5.4049 -1.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0856 5.9475 -2.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3623 5.5663 -1.2109 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5183 3.9553 -3.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3610 2.2789 -2.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5784 3.7086 -1.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0060 -1.0323 -2.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5764 -2.1652 -2.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7535 -1.2585 -3.9302 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8897 -0.3594 -2.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3375 -0.7607 -0.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2051 0.8216 -1.2727 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8310 0.7710 0.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1107 -0.4433 2.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9901 -2.0416 3.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8567 -0.5141 3.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6514 -2.0023 0.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5460 -3.3513 -0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7521 -3.6523 0.6011 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1659 -2.8919 -0.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 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 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 24 25 1 0 25 26 1 0 19 27 1 0 27 28 1 0 16 29 1 0 15 30 1 0 30 31 1 0 14 32 1 0 32 33 1 0 11 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 3 38 39 1 0 37 40 1 0 10 41 1 0 10 42 1 0 9 43 1 0 23 8 1 0 17 12 1 0 23 18 1 0 26 20 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 4 48 1 0 4 49 1 0 4 50 1 0 8 51 1 0 9 52 1 0 11 53 1 0 13 54 1 0 22 55 1 0 25 56 1 0 25 57 1 0 28 58 1 0 28 59 1 0 28 60 1 0 29 61 1 0 31 62 1 0 31 63 1 0 31 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 38 68 1 0 39 69 1 0 39 70 1 0 39 71 1 0 40 72 1 0 40 73 1 0 40 74 1 0 41 75 1 0 41 76 1 0 41 77 1 0 42 78 1 0 43 79 1 0 43 80 1 0 43 81 1 0 M END

Standard InCHIKey	JSLINKYCDFQONE-NWHFWVMISA-N
Standard InCHI	InChI=1S/C32H38O11/c1-10-15(3)30(34)42-25-17(5)32(6,36)29(43-31(35)16(4)11-2)19-13-20(37-7)26(38-8)24(33)22(19)23-18(25)12-21-27(28(23)39-9)41-14-40-21/h10-13,17,25,29,33,36H,14H2,1-9H3/b15-10-,16-11-/t17-,25+,29-,32+/m0/s1
SMILES	CC=C(C)C(=O)OC1C(C(C(C2=CC(=C(C(=C2C3=C(C4=C(C=C13)OCO4)OC)O)OC)OC)OC(=O)C(=CC)C)(C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	598.24	Volume:	598.13 ? Van der Waals volume.
Dense:	1.0	LogP:	3.697 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.083 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.498 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	26.0
TPSA:	139.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.316	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.622	Fsp³:	0.438
MCE-18:	102.957 ? 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:	0.141	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.379 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.49 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.097	Promiscuous compounds:	0.224

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151	MDCK Permeability:	-4.776
Pgp-inhibitor:	0.051	Pgp-substrate:	0.125
PAMPA:	0.905 ? 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):	0.17
20% Bioavailability (F20%):	0.801	30% Bioavailability (F30%):	0.38
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111	MRP1:	0.998
Plasma Protein Binding (PPB):	96.158%	Volume Distribution (VD):	-0.141
Fu:	4.061% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.642
OATP1B3 inhibitor:	0.886	BCRP inhibitor:	0.003
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.966	CYP2C19-substrate:	0.346
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.409	CYP2D6-substrate:	0.994
CYP3A4-inhibitor:	0.974	CYP3A4-substrate:	0.503
CYP2B6-substrate:	0.032	CYP2C8-inhibitor:	0.112
HLM stability:	0.92 ? 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):

3.224

Half-life (T1/2):

1.237

ADMET: Toxicity

hERG Blockers:	0.144	hERG Blockers (10um):	0.487
Human Hepatotoxicity (H-HT):	0.613	Drug-induced Liver Injury (DILI):	0.838
AMES Toxicity:	0.671	Rat Oral Acute Toxicity:	0.558
Maximum Recommended Daily Dose:	0.912	Skin Sensitization:	0.984
Carcinogencity:	0.893	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.576
Drug-induced Neurotoxicity:	0.687	Ototoxicity:	0.773
Hematotoxicity:	0.63	Drug-induced Nephrotoxicity:	0.942
Genotoxicity:	0.813	RPMI-8226 Immunitoxicity:	0.543
A549 Cytotoxicity:	0.551	Hek293 Cytotoxicity:	0.654
BCF:	1.361 ? 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:	3.966 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.783 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.005 ? 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
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[16268562]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792420]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17608535]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	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
ED50	3
Activity	1

Activity Type	# Activity
Cell line	2
Others	1
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
NPT165	Cell line	HeLa	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[15387649]
NPT91	Cell line	KB	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[15387649]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>=	5.0	ug ml-1	PMID[16792420]
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	1.9	%	PMID[19012394]

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 NPC475592 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	11111
0.1-0.2	35971
0.2-0.3	2571
0.3-0.4	131
0.4-0.5	45
0.5-0.6	19
0.6-0.7	6
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
0.7353	Intermediate Similarity	NPC308739
0.7123	Intermediate Similarity	NPC483406
0.6757	Remote Similarity	NPC476065
0.641	Remote Similarity	NPC485504
0.6286	Remote Similarity	NPC474393
0.6286	Remote Similarity	NPC474347
0.6081	Remote Similarity	NPC198461
0.6	Remote Similarity	NPC473736
0.5921	Remote Similarity	NPC126405
0.5921	Remote Similarity	NPC53669
0.5921	Remote Similarity	NPC77237
0.5921	Remote Similarity	NPC297271
0.5921	Remote Similarity	NPC16791
0.5921	Remote Similarity	NPC217708
0.5823	Remote Similarity	NPC291977
0.5714	Remote Similarity	NPC327352
0.5714	Remote Similarity	NPC198129
0.5714	Remote Similarity	NPC252281
0.56	Remote Similarity	NPC312763
0.5556	Remote Similarity	NPC322426
0.5455	Remote Similarity	NPC24562
0.5432	Remote Similarity	NPC483405
0.5405	Remote Similarity	NPC316989
0.5333	Remote Similarity	NPC73467
0.5333	Remote Similarity	NPC85141
0.519	Remote Similarity	NPC470916
0.5125	Remote Similarity	NPC477885

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4142
0.1-0.2	4937
0.2-0.3	70
0.3-0.4	1
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