NPASS Compound

Natural Product: NPC608249

Natural Product ID	NPC608249
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FJAQNRBDVKIIKK-LFLQOBSNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL303984
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 86 90 0 0 0 0 0 0 0 0999 V2000 -8.5969 1.6470 -1.8709 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5659 2.0581 -1.0288 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4344 1.2511 -1.1472 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2027 0.6737 0.2558 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3941 -0.0139 0.5702 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2228 0.3143 1.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8973 1.2904 2.3350 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4600 -0.4080 1.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3372 -0.1322 2.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3858 -1.0275 2.9193 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1406 -1.8647 1.8511 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0277 -3.0069 1.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9912 -1.4652 1.2859 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9832 -0.1796 0.1969 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1036 -1.2443 -0.6917 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8235 0.6921 -0.3161 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7863 0.5422 0.5244 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4939 0.1506 0.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7992 0.1888 1.7479 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5151 -0.1823 1.8635 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -0.6150 0.7687 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5673 -0.9955 0.8595 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1955 -0.9364 2.0962 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2328 -1.4195 -0.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6230 -1.8032 -0.1850 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6520 -0.8558 -0.4032 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3340 0.3435 -0.6767 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0615 -1.2057 -0.3256 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5321 -2.4470 0.0352 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8981 -2.6987 0.0737 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8361 -1.7367 -0.2417 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2106 -2.0281 -0.1913 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3848 -0.4937 -0.6038 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2954 0.5990 -0.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9857 1.2446 0.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2731 1.3565 0.3078 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8330 2.0360 1.5044 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2256 0.8321 -0.6980 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0273 -0.2464 -0.6405 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5272 -1.4461 -1.4540 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1662 -1.8400 -2.4679 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2722 -1.0785 -1.4880 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5876 -0.6659 -0.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7563 -0.2851 -0.5572 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4867 -0.3797 -2.1262 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.2764 2.0308 -0.4261 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1958 2.0526 -1.4742 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6326 1.5306 -2.7721 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6627 3.4947 -1.7230 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9192 0.5958 -1.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4757 2.2815 -1.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3267 1.7304 -2.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5764 0.4442 -1.8842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0008 1.5195 0.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2084 0.6641 3.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2477 -1.1092 3.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5916 -3.4713 0.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9777 -2.5012 1.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2725 -3.6652 2.2589 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5571 -1.9163 0.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7460 -0.5404 1.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2951 -1.8043 -0.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6164 0.3860 -1.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3281 0.5239 2.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0489 -0.1535 2.8154 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5200 -0.0174 2.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8957 -2.7796 0.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8203 -3.2339 0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2547 -3.6858 0.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6777 -2.1578 0.6877 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0689 0.1720 -1.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7652 1.3814 -1.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3291 1.6616 0.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5981 2.7529 1.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0321 2.6077 2.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2732 1.3263 2.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2126 1.5246 -1.5680 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9871 -0.1633 -1.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2782 0.8509 -0.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6605 0.7480 -0.9290 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1837 2.0467 -3.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5647 1.7136 -2.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9080 0.4530 -2.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3851 3.7690 -0.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2302 3.5270 -2.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8198 4.1895 -1.6902 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 5 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 4 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 22 24 2 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 2 3 36 37 1 0 36 38 1 0 33 39 2 0 24 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 16 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 47 3 1 0 13 8 1 0 44 18 1 0 43 21 1 0 39 28 1 0 1 50 1 0 1 51 1 0 1 52 1 0 3 53 1 6 4 54 1 1 9 55 1 0 10 56 1 0 12 57 1 0 12 58 1 0 12 59 1 0 13 60 1 0 14 61 1 1 15 62 1 0 16 63 1 6 19 64 1 0 20 65 1 0 23 66 1 0 25 67 1 0 29 68 1 0 30 69 1 0 32 70 1 0 34 71 1 0 34 72 1 0 35 73 1 0 37 74 1 0 37 75 1 0 37 76 1 0 38 77 1 0 38 78 1 0 38 79 1 0 39 80 1 0 48 81 1 0 48 82 1 0 48 83 1 0 49 84 1 0 49 85 1 0 49 86 1 0 M END

Standard InCHIKey	FJAQNRBDVKIIKK-LFLQOBSNSA-N
Standard InCHI	InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1
SMILES	CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2Cl)OC1(C)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
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1007/s00253-016-7823-y]
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23013356]
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28625960]
NPO32477	Streptomyces sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56200	Streptomyces hygroscopicus DS 9751 (NRRL 3418)	Genus	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]

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
Ratio	4
Kd	1
IC50	9
Activity	2
Ratio IC50	1
MIC	40
Inhibition	1

Activity Type	# Activity
Individual protein	3
Single protein	6
Organism	40
Protein complex	6
Unchecked	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT322	Individual protein	DNA topoisomerase II beta	Homo sapiens	Ratio	=	1.7	n.a.	PMID[10522710]
NPT29830	Single protein	DNA gyrase subunit B	Escherichia coli	Kd	=	1.2	nM	PMID[21235241]
NPT29830	Single protein	DNA gyrase subunit B	Escherichia coli	IC50	=	73.0	nM	PMID[18347114]
NPT29830	Single protein	DNA gyrase subunit B	Escherichia coli	IC50	<	5.0	nM	PMID[18347114]
NPT29830	Single protein	DNA gyrase subunit B	Escherichia coli	Ratio IC50	n.a.	n.a.	n.a.	PMID[18347114]
NPT29830	Single protein	DNA gyrase subunit B	Escherichia coli	Ratio	=	1.7	n.a.	PMID[10522711]
NPT23922	Single protein	DNA gyrase subunit A	Staphylococcus aureus	IC50	=	0.648	ug.mL-1	PMID[28094220]
NPT4942	Individual protein	DNA gyrase subunit A	Escherichia coli K-12	Activity	=	1.6	uM	PMID[18347114]
NPT4941	Individual protein	Cell division inhibitor sulA	Escherichia coli K-12	Activity	<	1.0	uM	PMID[18347114]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	3000.0	nM	PMID[27143131]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	30.0	nM	PMID[28850227]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	2.0	ug.mL-1	PMID[27143131]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	1.0	ug.mL-1	PMID[18347114]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	0.25	ug.mL-1	PMID[18347114]
NPT28438	Unchecked	Unchecked	n.a.	Ratio	=	1.7	n.a.	PMID[10937727]
NPT29666	Protein complex	Topoisomerase IV	Staphylococcus aureus	IC50	=	10000.0	nM	PMID[27143131]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	16.0	ug.mL-1	PMID[18347114]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	<	0.04	ug.mL-1	PMID[10937727]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	<	0.04	ug.mL-1	PMID[10450985]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.04	ug.mL-1	PMID[10937727]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	<	0.04	ug.mL-1	PMID[10450985]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.04	ug.mL-1	PMID[10522710]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.6	ug.mL-1	PMID[10937727]
NPT28648	Protein complex	DNA gyrase	Escherichia coli	Ratio	=	1.7	n.a.	PMID[10450985]
NPT29137	Protein complex	DNA gyrase	Staphylococcus aureus	IC50	=	8.5	nM	PMID[29803359]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[18347114]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	<=	0.06	ug.mL-1	PMID[18347114]
NPT28648	Protein complex	DNA gyrase	Escherichia coli	IC50	=	30.0	nM	PMID[27143131]
NPT29137	Protein complex	DNA gyrase	Staphylococcus aureus	IC50	=	6.0	nM	PMID[27143131]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32.0	ug.mL-1	PMID[18347114]
NPT29137	Protein complex	DNA gyrase	Staphylococcus aureus	Inhibition	=	86.0	%	PMID[29803359]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	n.a.	n.a.	ug.mL-1	PMID[10937727]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.04	ug.mL-1	PMID[10522711]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[18347114]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.04	ug.mL-1	PMID[10450985]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.06	ug.mL-1	PMID[27143131]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<=	0.06	ug.mL-1	PMID[18347114]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.15	ug.mL-1	PMID[10450985]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	<	0.04	ug.mL-1	PMID[10522711]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	16.0	ug.mL-1	PMID[18347114]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	8.0	ug.mL-1	PMID[18347114]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.15	ug.mL-1	PMID[10522710]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	<	0.04	ug.mL-1	PMID[10522710]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2.0	ug.mL-1	PMID[18347114]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.15	ug.mL-1	PMID[10522711]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[18347114]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	n.a.	n.a.	ug.mL-1	PMID[10937727]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	n.a.	n.a.	ug.mL-1	PMID[10450985]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	32.0	ug.mL-1	PMID[18347114]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	<	0.04	ug.mL-1	PMID[10937727]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	n.a.	n.a.	ug.mL-1	PMID[10522710]

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
-	Mus musculus	LD50	=	2200.0	mg/kg	ToxVal

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 NPC608249 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	17546
0.1-0.2	31132
0.2-0.3	1165
0.3-0.4	5
0.4-0.5	3
0.5-0.6	5
0.6-0.7	2
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
0.6552	Remote Similarity	NPC257728
0.6116	Remote Similarity	NPC315858
0.5492	Remote Similarity	NPC486975
0.544	Remote Similarity	NPC257266
0.5424	Remote Similarity	NPC315298
0.5403	Remote Similarity	NPC485253
0.5189	Remote Similarity	NPC606511

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC608249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3108
0.1-0.2	6022
0.2-0.3	17
0.3-0.4	0
0.4-0.5	0
0.5-0.6	2
0.6-0.7	1
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
0.6552	Remote Similarity	NPD7585	Phase 4
0.544	Remote Similarity	NPD7583	Approved
0.5156	Remote Similarity	NPD7584	Approved

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