NPASS Compound

Natural Product: NPC479357

Natural Product ID	NPC479357
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BYGUTMLHOGUOQA-GABFZXAWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 128135 0 0 0 0 0 0 0 0999 V2000 -1.7015 0.6051 -2.3223 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2192 0.2405 -0.9640 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0156 -1.0098 -0.8946 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2368 -2.2916 -0.9268 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0395 -2.1846 -0.0217 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3582 -0.8882 -0.2513 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2162 0.2024 0.0038 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7506 -0.7198 0.5615 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8865 -0.3990 -0.2113 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3959 0.9112 0.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8435 1.0727 0.4753 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6672 -0.1633 0.6608 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3049 -0.7401 2.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2564 -1.1693 -0.3930 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4669 -0.6240 -1.7838 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8469 -0.0256 -1.9057 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7159 -0.3653 -0.7235 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1275 0.2049 0.5260 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9111 -0.2760 1.7157 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2821 -0.7390 1.4409 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0046 -0.1419 0.2724 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0825 -1.1269 -0.1220 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6025 1.1910 0.5705 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7377 1.7908 -0.8165 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2918 1.5226 -1.3050 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1395 0.0514 -0.9434 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6146 -0.6634 -2.0427 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8465 1.2120 1.3800 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1699 2.6951 1.6628 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5994 2.6478 1.9847 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2106 3.4414 2.7372 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1603 1.5768 1.3163 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1069 0.8015 0.6958 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8222 -1.5602 -0.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1441 -3.2025 -0.4129 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -2.6536 -2.2259 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4642 -3.8545 -2.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 -0.9752 0.3535 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0501 -1.0190 0.1813 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6449 -2.1167 1.0128 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5358 -1.6049 2.1015 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4655 -0.4993 1.7009 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0092 0.1074 0.4020 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6375 1.4154 0.0564 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0149 1.2887 -0.0496 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6672 2.4591 -0.3990 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3782 2.1480 -1.7246 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1103 0.8286 -1.4822 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.7426 0.8315 -0.1320 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8064 2.2282 0.4813 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3645 2.0100 1.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6304 1.4495 1.7482 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5588 2.7908 0.5951 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0711 0.3658 -0.1666 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1141 -0.1695 -1.4940 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2314 3.1640 -2.1077 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6150 0.2305 0.5012 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7838 -0.9525 1.6451 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6865 -1.2148 3.1637 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3034 -3.0693 0.2085 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8788 1.3570 -2.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4912 1.1673 -2.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2671 -0.2059 -2.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 1.0825 -0.6451 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7943 -1.0529 -1.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9012 -3.1080 -0.5497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3785 -2.3416 1.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1089 -0.7992 -1.3346 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5086 -0.3537 -1.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7700 1.3094 1.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1017 1.6525 -0.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2795 1.7830 -0.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9499 1.6418 1.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4263 -1.8395 2.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7288 -0.1783 2.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1882 -0.5833 2.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8592 -2.0779 -0.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6600 0.1583 -1.9095 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2536 -1.3855 -2.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7243 1.0609 -2.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3211 -0.3832 -2.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7664 -1.4867 -0.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2539 1.3093 0.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8229 0.4974 2.5068 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3370 -1.1603 2.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9112 -0.5383 2.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3169 -1.8662 1.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5022 -1.9469 -0.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7827 -0.7662 -0.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5180 -1.6770 0.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8287 1.8567 1.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8737 2.8662 -0.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4517 1.2837 -1.4643 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6712 2.1773 -0.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1954 1.7235 -2.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0743 -1.4781 -2.1663 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7254 0.7578 2.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5315 3.0250 2.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9485 3.3099 0.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0957 1.1535 -0.3430 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3849 -0.2666 0.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5573 -2.2719 -0.9535 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7813 -2.0873 0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0467 -3.1375 -1.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5853 -3.7077 -2.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2507 -4.6807 -1.8619 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2685 -4.1321 -3.6331 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2618 -1.1376 -0.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8287 -2.7022 1.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1006 -2.4849 2.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3549 0.3063 2.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1750 -0.5776 -0.4609 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1911 1.8221 -0.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4088 2.1540 0.8391 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9424 3.2890 -0.5262 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5578 2.0229 -2.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7949 0.5825 -2.3153 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2148 0.1813 0.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5102 2.8315 -0.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7121 1.2778 2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4509 2.9394 2.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1252 2.0410 1.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0999 -0.6109 0.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4677 -1.0716 -1.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0129 2.8391 -2.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3329 -0.3073 2.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7830 -0.2660 3.3864 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4561 -3.8541 0.8245 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 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 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 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 23 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 5 35 1 0 4 36 1 0 36 37 1 0 3 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 43 57 1 0 42 58 1 0 41 59 1 0 40 60 1 0 7 2 1 0 34 9 1 0 57 39 1 0 18 12 1 0 26 21 1 0 33 28 1 0 53 46 1 0 26 17 1 0 1 61 1 0 1 62 1 0 1 63 1 0 2 64 1 1 3 65 1 6 4 66 1 1 5 67 1 1 6 68 1 6 9 69 1 6 10 70 1 0 10 71 1 0 11 72 1 0 11 73 1 0 13 74 1 0 13 75 1 0 13 76 1 0 14 77 1 6 15 78 1 0 15 79 1 0 16 80 1 0 16 81 1 0 17 82 1 1 18 83 1 6 19 84 1 0 19 85 1 0 20 86 1 0 20 87 1 0 22 88 1 0 22 89 1 0 22 90 1 0 23 91 1 1 24 92 1 0 24 93 1 0 25 94 1 0 25 95 1 0 27 96 1 0 28 97 1 1 29 98 1 0 29 99 1 0 33100 1 0 33101 1 0 34102 1 0 34103 1 0 35104 1 0 37105 1 0 37106 1 0 37107 1 0 39108 1 6 40109 1 1 41110 1 1 42111 1 1 43112 1 6 44113 1 0 44114 1 0 46115 1 6 47116 1 6 48117 1 6 49118 1 1 50119 1 6 51120 1 0 51121 1 0 52122 1 0 54123 1 0 55124 1 0 56125 1 0 58126 1 0 59127 1 0 60128 1 0 M END

Standard InCHIKey	BYGUTMLHOGUOQA-GABFZXAWSA-N
Standard InCHI	InChI=1S/C42H68O18/c1-18-35(60-38-33(50)31(48)29(46)26(59-38)17-55-37-32(49)30(47)28(45)25(15-43)58-37)36(53-4)34(51)39(56-18)57-21-7-10-40(2)20(14-21)5-6-24-23(40)8-11-41(3)22(9-12-42(24,41)52)19-13-27(44)54-16-19/h18-26,28-39,43,45-52H,5-17H2,1-4H3/t18-,19+,20+,21-,22+,23-,24+,25+,26+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37+,38-,39-,40-,41+,42-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)[C@@H]2CC(=O)OC2)C1)O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)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
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Leaves	n.a.	n.a.	PMID[29072457]
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Stems	n.a.	n.a.	PMID[31820973]

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	4

Activity Type	# Activity
Cell line	4

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
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[31820973]
NPT91	Cell line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[31820973]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[31820973]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	>	10000.0	nM	PMID[31820973]

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 NPC479357 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	20246
0.1-0.2	25332
0.2-0.3	3180
0.3-0.4	896
0.4-0.5	127
0.5-0.6	36
0.6-0.7	25
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC479353
0.9286	High Similarity	NPC479354
0.828	Intermediate Similarity	NPC479358
0.7895	Intermediate Similarity	NPC486144
0.7895	Intermediate Similarity	NPC486145
0.7895	Intermediate Similarity	NPC486147
0.7895	Intermediate Similarity	NPC486148
0.7604	Intermediate Similarity	NPC479360
0.7604	Intermediate Similarity	NPC479359
0.7263	Intermediate Similarity	NPC486143
0.7263	Intermediate Similarity	NPC486142
0.7263	Intermediate Similarity	NPC486149
0.7255	Intermediate Similarity	NPC474423
0.7157	Intermediate Similarity	NPC488945
0.7157	Intermediate Similarity	NPC488946
0.7	Intermediate Similarity	NPC486136
0.6979	Remote Similarity	NPC231518
0.6979	Remote Similarity	NPC488944
0.6863	Remote Similarity	NPC475419
0.6842	Remote Similarity	NPC30483
0.6842	Remote Similarity	NPC470897
0.6635	Remote Similarity	NPC486134
0.6635	Remote Similarity	NPC486141
0.6633	Remote Similarity	NPC488941
0.6633	Remote Similarity	NPC488940
0.6569	Remote Similarity	NPC488943
0.6569	Remote Similarity	NPC488942
0.6538	Remote Similarity	NPC120390
0.6476	Remote Similarity	NPC474908
0.6413	Remote Similarity	NPC479351
0.6413	Remote Similarity	NPC479352
0.64	Remote Similarity	NPC486135
0.64	Remote Similarity	NPC486137
0.6346	Remote Similarity	NPC475590
0.6337	Remote Similarity	NPC232785
0.6337	Remote Similarity	NPC486139
0.6154	Remote Similarity	NPC486131
0.6147	Remote Similarity	NPC488947
0.6105	Remote Similarity	NPC5311
0.61	Remote Similarity	NPC236973
0.6095	Remote Similarity	NPC486128
0.5962	Remote Similarity	NPC486146
0.5818	Remote Similarity	NPC486133
0.5818	Remote Similarity	NPC486150
0.5673	Remote Similarity	NPC475629
0.5636	Remote Similarity	NPC74259
0.5631	Remote Similarity	NPC292467
0.5631	Remote Similarity	NPC40749
0.5577	Remote Similarity	NPC486130
0.5565	Remote Similarity	NPC486152
0.5524	Remote Similarity	NPC486127
0.5514	Remote Similarity	NPC488939
0.5505	Remote Similarity	NPC488938
0.5505	Remote Similarity	NPC488937
0.5408	Remote Similarity	NPC99620
0.537	Remote Similarity	NPC329986
0.537	Remote Similarity	NPC140092
0.5333	Remote Similarity	NPC32177
0.5333	Remote Similarity	NPC469756
0.5333	Remote Similarity	NPC275901
0.531	Remote Similarity	NPC194716
0.53	Remote Similarity	NPC77299
0.53	Remote Similarity	NPC480906
0.5283	Remote Similarity	NPC188234
0.5273	Remote Similarity	NPC486132
0.5248	Remote Similarity	NPC480914
0.5182	Remote Similarity	NPC486138
0.5182	Remote Similarity	NPC276838
0.514	Remote Similarity	NPC480910
0.514	Remote Similarity	NPC240070
0.514	Remote Similarity	NPC480909
0.5135	Remote Similarity	NPC475219
0.5048	Remote Similarity	NPC480907
0.5046	Remote Similarity	NPC208193
0.5043	Remote Similarity	NPC486140
0.5043	Remote Similarity	NPC117445
0.5043	Remote Similarity	NPC308262

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6920
0.1-0.2	2135
0.2-0.3	76
0.3-0.4	9
0.4-0.5	9
0.5-0.6	0
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
0.6979	Remote Similarity	NPD8033	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