NPASS Compound

Natural Product: NPC163392

Natural Product ID	NPC163392
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tasipeptin B
IUPAC Name	N-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]butanamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508619
PubChem CID	9987747
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

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 117119 0 0 0 0 0 0 0 0999 V2000 6.9318 -4.9230 1.7125 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1346 -3.8647 1.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6300 -2.5024 1.4527 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8507 -1.4152 0.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9180 -1.6966 -0.0599 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0801 -0.8262 -0.8023 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0175 -1.7007 -1.4776 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7110 -2.6692 -2.4447 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2861 -2.3952 -0.5149 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9248 -2.2593 -0.3953 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3002 -1.5002 -1.1554 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1956 -3.0179 0.6417 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5597 -4.4821 0.4379 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0222 -4.7574 0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0796 -4.9817 -0.9002 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2017 -2.8173 0.6166 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8728 -2.1386 1.4298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3760 -1.9837 1.3159 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8907 -2.7127 0.1267 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3610 -2.5999 -0.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2576 -3.4454 0.5374 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6154 -3.3105 0.3526 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1389 -2.2933 -0.4404 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2365 -1.4372 -1.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8820 -1.5892 -0.8270 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5939 -0.5581 1.3214 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2422 0.0508 2.4220 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1628 0.2822 0.3073 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5518 -0.3122 -0.5649 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3487 1.7684 0.1728 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7777 2.0664 -0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1821 3.4804 -0.2171 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7017 3.5073 -0.4804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9835 4.2799 1.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4061 2.2502 -0.8132 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5722 2.3913 -2.2164 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2155 2.4825 -2.9296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5896 3.7717 -2.4443 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2804 3.7036 -0.9320 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0889 2.5691 -0.4287 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6373 1.7989 0.3875 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0540 3.5303 -0.7715 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2296 3.4346 -0.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0161 2.6030 0.2989 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9203 3.4201 1.1353 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9737 4.2107 0.4637 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7477 4.9367 1.5806 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9671 3.4454 -0.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5674 1.4421 -0.3096 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3918 0.2227 -0.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5532 -0.0952 1.0338 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0610 4.1357 -1.6078 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3536 1.4006 -2.7934 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3176 -1.4620 2.5113 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2159 -0.1087 1.0730 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4458 -5.6134 1.0038 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7138 -4.4758 2.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2651 -5.5225 2.3975 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3149 -3.9856 -0.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0651 -4.0100 1.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4674 -2.4075 2.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6944 -2.3738 1.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6812 -0.3755 -1.6387 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3273 -1.0661 -2.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9693 -3.0469 -3.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2338 -3.4723 -1.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4903 -2.1438 -3.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6158 -2.6558 1.6209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0274 -5.0325 1.2692 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4799 -3.9662 1.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2037 -5.7378 1.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5515 -4.7742 -0.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6686 -5.8143 -0.7608 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4066 -4.1858 -1.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9159 -5.3770 -1.5412 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7876 -2.4817 2.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3307 -2.4940 -0.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7026 -3.8055 0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9194 -4.2544 1.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3442 -3.9713 0.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2079 -2.1938 -0.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5929 -0.6279 -1.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2290 -0.8863 -1.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3309 -0.1350 2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9511 -0.4885 3.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0347 1.1334 2.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0956 2.1827 1.1615 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3908 1.6237 0.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1446 1.4860 -0.9870 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7507 3.9670 -1.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2630 3.2310 0.4178 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0039 4.4793 -0.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8840 2.7150 -1.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8366 3.6415 1.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8514 4.9332 1.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1200 4.9822 0.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0355 3.3675 -2.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6037 1.5962 -2.8216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4561 2.6261 -4.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3416 4.5717 -2.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3125 4.0605 -3.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6306 4.6719 -0.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2062 2.2223 0.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2641 4.1666 1.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3458 2.8123 1.9680 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5896 5.0475 -0.1677 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0263 5.3424 2.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3426 4.1568 2.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4349 5.6850 1.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7941 3.0356 0.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4906 4.1850 -1.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5412 2.6935 -1.0197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5220 0.4331 1.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6279 4.3827 -2.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1931 1.7540 -3.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4912 -1.7423 2.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1368 0.6027 0.3441 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 2 3 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 12 16 1 0 16 17 2 3 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 18 26 1 0 26 27 1 0 26 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 30 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 2 0 39 42 1 0 42 43 2 3 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 46 48 1 0 44 49 1 0 49 50 2 3 50 51 1 0 43 52 1 0 36 53 1 0 17 54 1 0 4 55 1 0 50 6 1 0 25 20 1 0 40 35 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 0 3 62 1 0 6 63 1 6 7 64 1 6 8 65 1 0 8 66 1 0 8 67 1 0 12 68 1 1 13 69 1 0 14 70 1 0 14 71 1 0 14 72 1 0 15 73 1 0 15 74 1 0 15 75 1 0 18 76 1 1 19 77 1 0 19 78 1 0 21 79 1 0 22 80 1 0 23 81 1 0 24 82 1 0 25 83 1 0 27 84 1 0 27 85 1 0 27 86 1 0 30 87 1 1 31 88 1 0 31 89 1 0 32 90 1 0 33 91 1 0 33 92 1 0 33 93 1 0 34 94 1 0 34 95 1 0 34 96 1 0 36 97 1 1 37 98 1 0 37 99 1 0 38100 1 0 38101 1 0 39102 1 1 44103 1 1 45104 1 0 45105 1 0 46106 1 0 47107 1 0 47108 1 0 47109 1 0 48110 1 0 48111 1 0 48112 1 0 51113 1 0 52114 1 0 53115 1 0 54116 1 0 55117 1 0 M END

Standard InCHIKey	SLJZYOVZWGGRQB-GRYOGVIMSA-N
Standard InCHI	InChI=1S/C40H62N6O9/c1-10-14-31(47)43-34-25(8)55-40(54)33(24(6)7)44-36(50)29(21-26-15-12-11-13-16-26)45(9)39(53)30(20-23(4)5)46-32(48)18-17-27(38(46)52)41-35(49)28(19-22(2)3)42-37(34)51/h11-13,15-16,22-25,27-30,32-34,48H,10,14,17-21H2,1-9H3,(H,41,49)(H,42,51)(H,43,47)(H,44,50)/t25-,27+,28+,29+,30+,32-,33+,34+/m1/s1
SMILES	CCCC(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccccc2)N(C)C(=O)[C@H](CC(C)C)N2[C@@H](CC[C@@H](C2=O)N=C([C@H](CC(C)C)N=C1O)O)O)O)O

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
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12350160]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762794]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	Sunday Island, Papua New Guinea	n.a.	PMID[18163584]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[20687534]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	Panamanian	n.a.	PMID[24164245]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24588245]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28055219]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29808677]

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	1

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	820.0	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 NPC163392 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	14017
0.1-0.2	33645
0.2-0.3	1922
0.3-0.4	198
0.4-0.5	33
0.5-0.6	26
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC239762
0.7475	Intermediate Similarity	NPC50016
0.6759	Remote Similarity	NPC40234
0.6733	Remote Similarity	NPC306804
0.6574	Remote Similarity	NPC107938
0.6545	Remote Similarity	NPC46009
0.6514	Remote Similarity	NPC294516
0.6509	Remote Similarity	NPC137627
0.6396	Remote Similarity	NPC102959
0.6316	Remote Similarity	NPC473404
0.6286	Remote Similarity	NPC273755
0.6239	Remote Similarity	NPC194671
0.6055	Remote Similarity	NPC279871
0.6019	Remote Similarity	NPC248670
0.6018	Remote Similarity	NPC159767
0.5982	Remote Similarity	NPC269750
0.5965	Remote Similarity	NPC155506
0.5943	Remote Similarity	NPC62104
0.5752	Remote Similarity	NPC248822
0.5739	Remote Similarity	NPC476227
0.5667	Remote Similarity	NPC240130
0.5664	Remote Similarity	NPC45037
0.5625	Remote Similarity	NPC5719
0.5625	Remote Similarity	NPC489102
0.5603	Remote Similarity	NPC302715
0.5575	Remote Similarity	NPC22883
0.5565	Remote Similarity	NPC294951
0.5478	Remote Similarity	NPC471526
0.5478	Remote Similarity	NPC63040
0.5385	Remote Similarity	NPC230611
0.5378	Remote Similarity	NPC65714
0.5378	Remote Similarity	NPC473371
0.5317	Remote Similarity	NPC281049
0.5263	Remote Similarity	NPC471052
0.5246	Remote Similarity	NPC163961
0.5214	Remote Similarity	NPC471050
0.521	Remote Similarity	NPC487289
0.5207	Remote Similarity	NPC488263
0.5207	Remote Similarity	NPC61332
0.5133	Remote Similarity	NPC1390
0.5085	Remote Similarity	NPC194699

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC163392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2936
0.1-0.2	5848
0.2-0.3	358
0.3-0.4	7
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