NPASS Compound

Natural Product: NPC272015

Natural Product ID	NPC272015
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-[Beta-D-Glucopyranosyl(1->2)-O-Beta-D-Xylopyranosyl]-Stigmasterol
IUPAC Name	(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2381688
PubChem CID	71615307
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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 116121 0 0 0 0 0 0 0 0999 V2000 9.8821 0.4985 2.6026 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0706 1.5807 1.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8136 1.2296 0.4771 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0866 1.0622 -0.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7316 0.7114 -1.7503 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8666 2.3583 -0.3340 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9336 0.0290 0.3389 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6890 0.1265 -0.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8271 -1.0395 -0.3019 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5188 -1.0426 0.3483 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4916 -0.8922 1.8487 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0513 -0.4553 2.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3707 -0.5453 0.8583 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4948 -0.0305 -0.0566 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8829 1.3635 0.2904 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0177 -0.1764 -1.4656 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 0.6016 -1.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6615 -0.0399 -0.7300 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0826 0.1853 0.7049 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1419 -0.3387 1.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2531 -0.2187 1.2964 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6543 0.1339 0.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7183 0.4723 -1.0141 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7019 1.9628 -1.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3477 -0.1675 -2.2571 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1346 -1.3993 -1.8842 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -1.1096 -1.0234 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1000 0.1704 -0.2122 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5200 -1.1318 -1.7053 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3263 -2.1505 -1.2011 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3490 -3.2249 -2.1478 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5594 -3.2889 -2.8244 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7046 -3.7180 -1.8995 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4972 -3.0180 -0.5921 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7328 -1.7291 -0.8907 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8247 -0.9242 0.2302 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3228 0.3404 -0.0558 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3842 1.2783 0.2948 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6731 2.1022 1.3432 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3958 1.5163 2.7151 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0499 1.2248 2.7916 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9964 2.7840 1.3374 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9071 2.1224 0.3396 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6991 0.6075 0.5000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6999 0.0021 -0.2882 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2193 2.3847 0.6560 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8969 4.1607 1.1159 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6281 -2.8373 0.1534 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7341 -5.1040 -1.7662 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5582 -2.3165 0.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3929 0.3106 3.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9115 0.8773 2.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8484 -0.3969 1.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6244 2.5534 1.9072 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1100 1.7566 2.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2828 2.0984 0.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7434 0.2551 0.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5808 0.9971 -2.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5058 -0.3766 -1.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8669 1.3340 -2.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7456 2.3056 0.3685 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1919 3.1592 0.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2134 2.6025 -1.3648 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2758 -0.9415 0.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4060 1.1218 -0.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6596 -1.2495 -1.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0370 -2.0503 0.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6305 -1.8993 2.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1498 -0.1332 2.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0042 0.5666 2.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5609 -1.2049 2.8532 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1983 -1.6019 0.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0401 1.9916 0.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1750 1.8677 -0.6760 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6494 1.4284 1.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8971 -1.2321 -1.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7428 0.3672 -2.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9204 1.6139 -1.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4116 0.6643 -2.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6739 -1.1250 -0.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1707 1.2811 0.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4062 -1.4296 1.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3483 0.2197 2.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0147 -0.4553 2.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1346 2.4899 -0.7651 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7835 2.1935 -2.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6306 2.4434 -0.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5192 -0.4931 -2.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9613 0.5516 -2.8248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4125 -2.0889 -1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4366 -1.8845 -2.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3277 -1.9176 -0.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7138 0.0860 0.7171 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4058 1.0165 -0.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8304 -2.6245 -0.3235 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8083 -2.3976 -3.4128 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4554 -4.1337 -3.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6514 -3.3499 -2.3509 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7686 -3.6381 0.0182 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1026 -1.2167 -1.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4613 0.3631 -1.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9046 2.9466 1.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0481 0.6962 3.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6190 2.3531 3.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5292 2.0590 2.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4959 2.6346 2.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6583 2.4261 -0.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8534 0.3755 1.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2582 -0.2852 -1.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7760 1.7124 0.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5575 4.4354 0.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4369 -2.9125 1.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7819 -5.3840 -1.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8914 -3.1976 0.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8434 -2.2593 1.2276 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4474 -2.5100 -0.4300 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 4 6 1 0 3 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 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 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 34 48 1 0 33 49 1 0 9 50 1 0 14 10 1 0 23 18 1 0 35 30 1 0 44 37 1 0 19 13 1 0 28 22 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 0 2 55 1 0 3 56 1 6 4 57 1 0 5 58 1 0 5 59 1 0 5 60 1 0 6 61 1 0 6 62 1 0 6 63 1 0 7 64 1 0 8 65 1 0 9 66 1 6 10 67 1 1 11 68 1 0 11 69 1 0 12 70 1 0 12 71 1 0 13 72 1 6 15 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 0 17 79 1 0 18 80 1 6 19 81 1 1 20 82 1 0 20 83 1 0 21 84 1 0 24 85 1 0 24 86 1 0 24 87 1 0 25 88 1 0 25 89 1 0 26 90 1 0 26 91 1 0 27 92 1 1 28 93 1 0 28 94 1 0 30 95 1 1 32 96 1 0 32 97 1 0 33 98 1 6 34 99 1 1 35100 1 6 37101 1 6 39102 1 6 40103 1 0 40104 1 0 41105 1 0 42106 1 1 43107 1 6 44108 1 1 45109 1 0 46110 1 0 47111 1 0 48112 1 0 49113 1 0 50114 1 0 50115 1 0 50116 1 0 M END

Standard InCHIKey	RYRHMRRZWNWNKA-YSJQLQQBSA-N
Standard InCHI	InChI=1S/C40H66O10/c1-7-23(21(2)3)9-8-22(4)27-12-13-28-26-11-10-24-18-25(14-16-39(24,5)29(26)15-17-40(27,28)6)48-38-36(32(43)30(42)20-47-38)50-37-35(46)34(45)33(44)31(19-41)49-37/h8-10,21-23,25-38,41-46H,7,11-20H2,1-6H3/b9-8+/t22-,23-,25+,26+,27-,28+,29+,30-,31-,32+,33-,34+,35-,36-,37+,38+,39+,40-/m1/s1
SMILES	CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O[C@@H]1OC[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O)C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33322	caesalpinia volkensii	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[23562058]

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	2

Activity Type	# Activity
Organism	2

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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2740.0	nM	DrugMatrix in vivo data: Pathology
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4440.0	nM	PMID[21070010]

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 NPC272015 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	19625
0.1-0.2	24829
0.2-0.3	3785
0.3-0.4	1427
0.4-0.5	139
0.5-0.6	44
0.6-0.7	3
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
0.8133	Intermediate Similarity	NPC158088
0.6585	Remote Similarity	NPC22140
0.6585	Remote Similarity	NPC243728
0.6	Remote Similarity	NPC285231
0.5976	Remote Similarity	NPC207617
0.5976	Remote Similarity	NPC607440
0.5862	Remote Similarity	NPC282669
0.5644	Remote Similarity	NPC470748
0.5534	Remote Similarity	NPC98696
0.5534	Remote Similarity	NPC486388
0.5446	Remote Similarity	NPC306991
0.5446	Remote Similarity	NPC94272
0.5437	Remote Similarity	NPC307642
0.5426	Remote Similarity	NPC486114
0.5408	Remote Similarity	NPC86020
0.534	Remote Similarity	NPC305423
0.534	Remote Similarity	NPC113044
0.534	Remote Similarity	NPC283829
0.534	Remote Similarity	NPC161676
0.5312	Remote Similarity	NPC181845
0.5281	Remote Similarity	NPC21064
0.5263	Remote Similarity	NPC296686
0.5258	Remote Similarity	NPC295389
0.5227	Remote Similarity	NPC473890
0.5227	Remote Similarity	NPC267510
0.5222	Remote Similarity	NPC470434
0.5196	Remote Similarity	NPC295980
0.5192	Remote Similarity	NPC600116
0.5185	Remote Similarity	NPC475182
0.5185	Remote Similarity	NPC156789
0.5179	Remote Similarity	NPC249265
0.5169	Remote Similarity	NPC21568
0.5155	Remote Similarity	NPC262080
0.514	Remote Similarity	NPC477809
0.5138	Remote Similarity	NPC73243
0.5138	Remote Similarity	NPC244086
0.5138	Remote Similarity	NPC84956
0.5104	Remote Similarity	NPC489081
0.5094	Remote Similarity	NPC40440
0.5052	Remote Similarity	NPC318135
0.5052	Remote Similarity	NPC165439
0.5046	Remote Similarity	NPC480555
0.5046	Remote Similarity	NPC150372
0.5045	Remote Similarity	NPC247037
0.5044	Remote Similarity	NPC218571
0.5044	Remote Similarity	NPC160084
0.5044	Remote Similarity	NPC487615
0.5044	Remote Similarity	NPC473474

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC272015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6783
0.1-0.2	2204
0.2-0.3	146
0.3-0.4	14
0.4-0.5	3
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