NPASS Compound

Natural Product: NPC308739

Natural Product ID	NPC308739
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kadsurarin
IUPAC Name	n.a.
Synonyms	Kadsurarin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL464501
PubChem CID	44567619
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 77 80 0 0 0 0 0 0 0 0999 V2000 6.1065 -0.7634 2.7050 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2212 -0.5391 1.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1543 -0.2718 0.5324 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3268 -0.0553 -0.9251 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8586 -0.1986 1.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6378 -0.3722 2.3719 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7643 0.0913 0.3684 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4443 0.2016 0.8053 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5313 -0.7937 0.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1969 -1.9803 0.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5646 -3.0656 -0.5637 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7573 -2.9922 -0.9970 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4566 -1.8221 -0.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8097 -0.7719 -0.2454 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8430 0.2540 -0.1586 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8335 1.6184 -0.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0302 2.2714 -0.3427 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1677 1.6300 0.1160 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1014 0.2687 0.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9303 -0.4356 0.3061 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7720 -1.7687 0.6220 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4061 -2.2353 1.9037 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3528 -0.1288 0.8670 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2839 0.8811 0.4749 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4708 2.0576 0.3513 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8034 2.5773 -0.9552 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6111 2.1063 -0.6886 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0409 1.2818 -1.8705 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9618 1.6344 0.6449 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0124 1.8825 1.7561 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1395 2.3522 1.0468 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0732 3.8343 -0.4359 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3877 4.9553 -1.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4366 4.8411 -2.4229 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6549 6.2414 -0.5061 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7601 -1.6301 -1.2520 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0990 -1.1700 -2.5460 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4342 -4.0414 -1.5922 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1722 -4.9772 -0.8241 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2581 -4.2664 -0.7350 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6052 -4.3545 -0.2976 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7160 0.1367 3.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1397 -0.8931 3.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4939 -1.6490 2.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2208 -0.6011 0.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3834 -0.1987 -1.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0397 -0.8030 -1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7098 0.9558 -1.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4646 0.0024 1.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2315 -2.0484 0.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0831 3.3239 -0.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7569 -3.2657 2.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8768 -1.5596 2.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -2.1042 2.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0792 1.0145 1.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6522 0.5816 -0.5278 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9066 2.6366 -2.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1875 3.0880 -0.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5425 1.8806 -2.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6190 0.3736 -1.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1149 0.9143 -2.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3949 0.9463 2.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8310 2.5897 1.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5300 2.3842 2.5951 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2932 2.1456 2.0115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4334 6.8217 -1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7141 6.8385 -0.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0575 6.1115 0.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6744 -0.2351 -2.4273 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7918 -1.8762 -3.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2480 -1.0191 -3.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0802 -4.8065 0.2547 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8060 -5.9893 -1.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2535 -4.9682 -1.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6669 -4.1066 0.7819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2015 -3.6244 -0.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0359 -5.3437 -0.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 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 1 0 19 23 1 0 23 24 1 0 24 25 1 0 16 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 1 26 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 13 36 1 0 36 37 1 0 12 38 1 0 38 39 1 0 11 40 1 0 40 41 1 0 29 8 1 0 14 9 1 0 20 15 1 0 25 18 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 4 46 1 0 4 47 1 0 4 48 1 0 8 49 1 1 10 50 1 0 17 51 1 0 22 52 1 0 22 53 1 0 22 54 1 0 24 55 1 0 24 56 1 0 26 57 1 6 27 58 1 6 28 59 1 0 28 60 1 0 28 61 1 0 30 62 1 0 30 63 1 0 30 64 1 0 31 65 1 0 35 66 1 0 35 67 1 0 35 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 39 72 1 0 39 73 1 0 39 74 1 0 41 75 1 0 41 76 1 0 41 77 1 0 M END

Standard InCHIKey	DHEFJFKRWXSOLG-XKIHEKSBSA-N
Standard InCHI	InChI=1S/C30H36O11/c1-10-14(2)29(32)41-28-18-12-19(34-6)24(35-7)26(36-8)22(18)21-17(11-20-25(27(21)37-9)39-13-38-20)23(40-16(4)31)15(3)30(28,5)33/h10-12,15,23,28,33H,13H2,1-9H3/b14-10-/t15-,23-,28+,30-/m0/s1
SMILES	C/C=C(/C)C(=O)O[C@@H]1c2cc(c(c(c2-c2c(cc3c(c2OC)OCO3)[C@H]([C@H](C)[C@]1(C)O)OC(=O)C)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	572.23	Volume:	566.175 ? Van der Waals volume.
Dense:	1.011	LogP:	3.008 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.928 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.873 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	25.0
TPSA:	128.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.367	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.401	Fsp³:	0.467
MCE-18:	100.045 ? 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:	0.162	Fluc inhibitor:	0.039 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.527 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.313 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.123	Promiscuous compounds:	0.241

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.075	MDCK Permeability:	-4.766
Pgp-inhibitor:	0.17	Pgp-substrate:	0.12
PAMPA:	0.771 ? 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):	0.006
20% Bioavailability (F20%):	0.625	30% Bioavailability (F30%):	0.049
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059	MRP1:	0.999
Plasma Protein Binding (PPB):	91.157%	Volume Distribution (VD):	-0.162
Fu:	8.324% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.03
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.918	CYP1A2-substrate:	0.711
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.554	CYP2C9-substrate:	0.294
CYP2D6-inhibitor:	0.015	CYP2D6-substrate:	0.97
CYP3A4-inhibitor:	0.95	CYP3A4-substrate:	0.92
CYP2B6-substrate:	0.398	CYP2C8-inhibitor:	0.537
HLM stability:	0.796 ? 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):

4.411

Half-life (T1/2):

1.034

ADMET: Toxicity

hERG Blockers:	0.095	hERG Blockers (10um):	0.389
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.948
AMES Toxicity:	0.873	Rat Oral Acute Toxicity:	0.554
Maximum Recommended Daily Dose:	0.92	Skin Sensitization:	0.956
Carcinogencity:	0.945	Eye Corrosion:	0.0
Eye Irritation:	0.1	Respiratory Toxicity:	0.627
Drug-induced Neurotoxicity:	0.859	Ototoxicity:	0.538
Hematotoxicity:	0.732	Drug-induced Nephrotoxicity:	0.944
Genotoxicity:	0.918	RPMI-8226 Immunitoxicity:	0.409
A549 Cytotoxicity:	0.592	Hek293 Cytotoxicity:	0.711
BCF:	0.985 ? 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:	3.444 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.101 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.31 ? 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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	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
EC50	1
Ratio	1
CC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	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
NPT1452	Cell line	C8166	Homo sapiens	CC50	>	200000.0	nM	PMID[15332840]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	168310.0	nM	PMID[10785421]
NPT2	Others	Unspecified	n.a.	Ratio	>	2.14	n.a.	Open TG-GATES in vivo data: Hematology

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 NPC308739 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	11514
0.1-0.2	35623
0.2-0.3	2449
0.3-0.4	176
0.4-0.5	51
0.5-0.6	23
0.6-0.7	10
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
0.7424	Intermediate Similarity	NPC126405
0.7424	Intermediate Similarity	NPC53669
0.7424	Intermediate Similarity	NPC77237
0.7424	Intermediate Similarity	NPC297271
0.7424	Intermediate Similarity	NPC16791
0.7424	Intermediate Similarity	NPC217708
0.7353	Intermediate Similarity	NPC475592
0.7333	Intermediate Similarity	NPC327352
0.7333	Intermediate Similarity	NPC198129
0.7333	Intermediate Similarity	NPC252281
0.7121	Intermediate Similarity	NPC198461
0.6562	Remote Similarity	NPC322426
0.6441	Remote Similarity	NPC326144
0.6377	Remote Similarity	NPC24562
0.6364	Remote Similarity	NPC316989
0.6364	Remote Similarity	NPC295297
0.619	Remote Similarity	NPC318286
0.6087	Remote Similarity	NPC312763
0.6053	Remote Similarity	NPC485504
0.6032	Remote Similarity	NPC327651
0.6	Remote Similarity	NPC321958
0.5972	Remote Similarity	NPC224472
0.5882	Remote Similarity	NPC325720
0.5882	Remote Similarity	NPC316676
0.5833	Remote Similarity	NPC470916
0.5797	Remote Similarity	NPC85141
0.5758	Remote Similarity	NPC321696
0.5753	Remote Similarity	NPC477885
0.5588	Remote Similarity	NPC76415
0.5588	Remote Similarity	NPC325122
0.5588	Remote Similarity	NPC218510
0.5588	Remote Similarity	NPC473989
0.541	Remote Similarity	NPC216434
0.541	Remote Similarity	NPC103448
0.541	Remote Similarity	NPC606558
0.5385	Remote Similarity	NPC29727
0.5278	Remote Similarity	NPC319749
0.5256	Remote Similarity	NPC483406
0.5211	Remote Similarity	NPC474393
0.5211	Remote Similarity	NPC474347
0.5128	Remote Similarity	NPC476065
0.5119	Remote Similarity	NPC477883
0.5082	Remote Similarity	NPC474295
0.5062	Remote Similarity	NPC473736

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC308739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4137
0.1-0.2	4924
0.2-0.3	85
0.3-0.4	4
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