NPASS Compound

Natural Product: NPC470720

Natural Product ID	NPC470720
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-Glucosyl-7-O-Beta-D-(2-O-Feruloyl)Glucosyl Kaempferol
IUPAC Name	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-7-yl]oxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206205
PubChem CID	21769758
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 94 99 0 0 0 0 0 0 0 0999 V2000 8.7592 2.5439 -5.3475 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8323 1.4929 -4.4424 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2742 1.4280 -3.1942 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4775 0.2822 -2.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9273 0.1943 -1.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1782 1.2572 -0.6824 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9657 2.4016 -1.4073 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5339 2.4803 -2.6950 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1329 3.4884 -0.9623 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1892 3.6311 -0.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5328 2.7251 0.7678 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6803 3.2434 1.5881 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6300 1.3830 0.8988 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9613 0.5361 1.8078 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9499 -0.2043 2.6417 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5784 -1.3984 1.9134 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4325 -2.2307 1.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7398 -1.4426 0.4614 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0247 -0.4055 1.0706 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1499 -0.9981 1.9704 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7970 -1.1336 1.8642 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0870 -1.7659 2.8944 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2704 -1.9400 2.8550 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9470 -1.4652 1.7489 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2665 -0.8458 0.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1246 -0.6688 0.7772 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9266 -0.4196 -0.2733 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2617 -0.5151 -0.4568 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0151 -1.1156 0.5086 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3273 -1.6000 1.6341 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9805 -2.1568 2.5324 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3927 -1.2602 0.4464 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3155 -0.3287 1.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8738 -0.9815 2.2733 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3770 -0.7824 2.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6659 0.6303 1.9529 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3162 0.7608 0.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2492 0.0063 0.1110 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4992 0.4350 -0.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2523 0.7097 -1.7377 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0194 0.8867 2.1034 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9882 -1.7397 1.6350 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3155 -0.3477 3.3847 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8037 0.0367 -1.6866 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0298 -0.1982 -2.1832 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5100 0.4195 -3.3496 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7039 1.2763 -3.9892 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4186 1.5641 -3.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9969 0.9357 -2.3869 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1504 1.9080 -5.1506 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9967 -2.5625 3.8587 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8948 -3.4861 0.6708 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7346 -3.2206 -0.3988 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3146 -2.0690 2.8917 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2544 -0.7793 3.7288 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2220 -0.7451 -3.0010 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8883 2.4202 -6.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6901 3.5270 -4.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6511 2.5506 -6.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1013 -0.7066 -0.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8391 1.1616 0.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3807 3.3706 -3.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4160 4.4648 -1.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7639 4.6800 -0.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3387 1.1685 2.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7084 0.4955 3.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2355 -1.0730 1.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7485 -2.5286 2.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4974 0.1220 0.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5975 -2.1525 3.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6121 -0.1620 -0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6560 0.5223 1.3605 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6109 -2.0478 2.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7266 -0.8765 3.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0987 1.3690 2.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0813 1.8320 0.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4113 0.9850 -0.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7815 -0.6541 -0.2634 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3288 -0.1506 -2.2510 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2425 1.1874 3.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8218 -2.6230 2.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2268 -0.9363 4.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6793 -0.9166 -1.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5149 0.1772 -3.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8079 2.2533 -4.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9776 1.1498 -2.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4714 2.2190 -5.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6052 -1.9696 4.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3549 -4.1562 1.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9534 -3.9544 0.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5039 -2.3199 -0.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3696 -3.0371 2.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7923 -1.5200 4.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0909 -1.7204 -2.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 3 10 11 1 0 11 12 2 0 11 13 1 0 13 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 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 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 37 39 1 0 39 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 28 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 47 50 1 0 23 51 1 0 17 52 1 0 52 53 1 0 16 54 1 0 15 55 1 0 4 56 1 0 8 3 1 0 19 14 1 0 26 21 1 0 30 24 1 0 38 33 1 0 49 44 1 0 1 57 1 0 1 58 1 0 1 59 1 0 5 60 1 0 6 61 1 0 8 62 1 0 9 63 1 0 10 64 1 0 14 65 1 0 15 66 1 0 16 67 1 0 17 68 1 0 19 69 1 0 22 70 1 0 26 71 1 0 33 72 1 0 34 73 1 0 35 74 1 0 36 75 1 0 37 76 1 0 39 77 1 0 39 78 1 0 40 79 1 0 41 80 1 0 42 81 1 0 43 82 1 0 45 83 1 0 46 84 1 0 48 85 1 0 49 86 1 0 50 87 1 0 51 88 1 0 52 89 1 0 52 90 1 0 53 91 1 0 54 92 1 0 55 93 1 0 56 94 1 0 M END

Standard InCHIKey	CRCKGUVNMGEOPI-ZAGNFOMMSA-N
Standard InCHI	InChI=1S/C37H38O19/c1-50-21-10-15(2-8-19(21)41)3-9-25(43)55-35-31(48)28(45)24(14-39)54-37(35)51-18-11-20(42)26-22(12-18)52-33(16-4-6-17(40)7-5-16)34(29(26)46)56-36-32(49)30(47)27(44)23(13-38)53-36/h2-12,23-24,27-28,30-32,35-42,44-45,47-49H,13-14H2,1H3/b9-3+/t23-,24-,27-,28-,30+,31+,32-,35-,36+,37-/m1/s1
SMILES	COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=C(C4=O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC=C(C=C6)O)O)CO)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
NPO3860.1	Allium victorialis	Under-species	n.a.	n.a.	Leaves	Taeback, GangWon province, Korea	2011-Jan	PMID[23149227]

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
Activity	1
IC50	1

Activity Type	# Activity
Cell line	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
NPT34	Cell line	BV-2	Mus musculus	Activity	=	105.9	%	PubChem BioAssay data set
NPT34	Cell line	BV-2	Mus musculus	IC50	=	21480.0	nM	DOI[10.1007/s00044-012-0253-1]

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 NPC470720 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	18274
0.1-0.2	27089
0.2-0.3	3242
0.3-0.4	754
0.4-0.5	325
0.5-0.6	134
0.6-0.7	20
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC470717
0.9091	High Similarity	NPC295625
0.8725	High Similarity	NPC470719
0.8687	High Similarity	NPC164704
0.8317	Intermediate Similarity	NPC470715
0.8095	Intermediate Similarity	NPC470713
0.74	Intermediate Similarity	NPC64425
0.729	Intermediate Similarity	NPC470712
0.7156	Intermediate Similarity	NPC470716
0.7	Intermediate Similarity	NPC470718
0.6771	Remote Similarity	NPC297987
0.661	Remote Similarity	NPC25946
0.6449	Remote Similarity	NPC35119
0.6436	Remote Similarity	NPC116458
0.6436	Remote Similarity	NPC246943
0.6327	Remote Similarity	NPC289667
0.6296	Remote Similarity	NPC32641
0.6296	Remote Similarity	NPC256188
0.6283	Remote Similarity	NPC480796
0.6271	Remote Similarity	NPC488078
0.6198	Remote Similarity	NPC199172
0.6195	Remote Similarity	NPC470416
0.6148	Remote Similarity	NPC21359
0.6148	Remote Similarity	NPC460984
0.614	Remote Similarity	NPC472993
0.6134	Remote Similarity	NPC488079
0.6111	Remote Similarity	NPC240306
0.61	Remote Similarity	NPC136042
0.608	Remote Similarity	NPC223860
0.604	Remote Similarity	NPC84362
0.5948	Remote Similarity	NPC25523
0.5943	Remote Similarity	NPC251417
0.5887	Remote Similarity	NPC480470
0.5882	Remote Similarity	NPC46420
0.5856	Remote Similarity	NPC139060
0.5842	Remote Similarity	NPC249281
0.581	Remote Similarity	NPC605784
0.576	Remote Similarity	NPC35924
0.5728	Remote Similarity	NPC24043
0.5728	Remote Similarity	NPC488080
0.5728	Remote Similarity	NPC169977
0.5726	Remote Similarity	NPC480472
0.5686	Remote Similarity	NPC77672
0.5686	Remote Similarity	NPC133671
0.5686	Remote Similarity	NPC135391
0.5686	Remote Similarity	NPC78263
0.5686	Remote Similarity	NPC250069
0.5673	Remote Similarity	NPC472459
0.5664	Remote Similarity	NPC205824
0.5652	Remote Similarity	NPC218161
0.562	Remote Similarity	NPC474093
0.562	Remote Similarity	NPC104910
0.5619	Remote Similarity	NPC611303
0.5614	Remote Similarity	NPC85751
0.5614	Remote Similarity	NPC19240
0.5607	Remote Similarity	NPC203050
0.5607	Remote Similarity	NPC225434
0.5607	Remote Similarity	NPC276377
0.5575	Remote Similarity	NPC104883
0.5575	Remote Similarity	NPC488679
0.5566	Remote Similarity	NPC120099
0.5566	Remote Similarity	NPC224530
0.5565	Remote Similarity	NPC36138
0.5546	Remote Similarity	NPC217520
0.5536	Remote Similarity	NPC472992
0.5505	Remote Similarity	NPC473682
0.55	Remote Similarity	NPC277532
0.5495	Remote Similarity	NPC150164
0.5487	Remote Similarity	NPC477628
0.5481	Remote Similarity	NPC64305
0.5481	Remote Similarity	NPC323593
0.5481	Remote Similarity	NPC203500
0.5478	Remote Similarity	NPC80068
0.547	Remote Similarity	NPC214621
0.547	Remote Similarity	NPC34267
0.5463	Remote Similarity	NPC170052
0.5463	Remote Similarity	NPC135846
0.5439	Remote Similarity	NPC210961
0.5424	Remote Similarity	NPC121703
0.5421	Remote Similarity	NPC22832
0.5421	Remote Similarity	NPC486578
0.5417	Remote Similarity	NPC480441
0.5391	Remote Similarity	NPC221288
0.5391	Remote Similarity	NPC270675
0.5391	Remote Similarity	NPC194836
0.5391	Remote Similarity	NPC472991
0.5391	Remote Similarity	NPC195685
0.5391	Remote Similarity	NPC91493
0.5391	Remote Similarity	NPC605081
0.5385	Remote Similarity	NPC483767
0.5385	Remote Similarity	NPC39360
0.5385	Remote Similarity	NPC483769
0.5385	Remote Similarity	NPC29763
0.5385	Remote Similarity	NPC210003
0.5385	Remote Similarity	NPC483768
0.5385	Remote Similarity	NPC483766
0.5379	Remote Similarity	NPC249560
0.537	Remote Similarity	NPC311830
0.5345	Remote Similarity	NPC76831
0.5339	Remote Similarity	NPC14187
0.5333	Remote Similarity	NPC219043
0.5333	Remote Similarity	NPC477895
0.5328	Remote Similarity	NPC139571
0.5327	Remote Similarity	NPC60735
0.5327	Remote Similarity	NPC26230
0.5327	Remote Similarity	NPC285197
0.5321	Remote Similarity	NPC488072
0.5321	Remote Similarity	NPC601586
0.5317	Remote Similarity	NPC138990
0.531	Remote Similarity	NPC186816
0.5304	Remote Similarity	NPC72016
0.5304	Remote Similarity	NPC606657
0.5283	Remote Similarity	NPC271692
0.528	Remote Similarity	NPC162394
0.5278	Remote Similarity	NPC101026
0.5278	Remote Similarity	NPC488077
0.5278	Remote Similarity	NPC609478
0.5259	Remote Similarity	NPC142142
0.5254	Remote Similarity	NPC223426
0.5234	Remote Similarity	NPC42773
0.5234	Remote Similarity	NPC45522
0.5229	Remote Similarity	NPC206123
0.521	Remote Similarity	NPC483765
0.5207	Remote Similarity	NPC48984
0.5189	Remote Similarity	NPC145038
0.5189	Remote Similarity	NPC8573
0.5189	Remote Similarity	NPC56077
0.5189	Remote Similarity	NPC281131
0.5189	Remote Similarity	NPC95090
0.5189	Remote Similarity	NPC253662
0.5189	Remote Similarity	NPC179950
0.5189	Remote Similarity	NPC277205
0.5189	Remote Similarity	NPC27408
0.5189	Remote Similarity	NPC37919
0.5189	Remote Similarity	NPC88789
0.5189	Remote Similarity	NPC491374
0.5185	Remote Similarity	NPC488071
0.5175	Remote Similarity	NPC470444
0.5156	Remote Similarity	NPC175429
0.5138	Remote Similarity	NPC243930
0.5138	Remote Similarity	NPC21666
0.5138	Remote Similarity	NPC80188
0.5138	Remote Similarity	NPC601144
0.5133	Remote Similarity	NPC163242
0.5133	Remote Similarity	NPC272068
0.5126	Remote Similarity	NPC484301
0.5126	Remote Similarity	NPC472994
0.5109	Remote Similarity	NPC475179
0.5096	Remote Similarity	NPC288084
0.5093	Remote Similarity	NPC325555
0.5093	Remote Similarity	NPC226304
0.5093	Remote Similarity	NPC599850
0.5089	Remote Similarity	NPC8856
0.5088	Remote Similarity	NPC65003
0.5088	Remote Similarity	NPC304741
0.5085	Remote Similarity	NPC195257
0.5085	Remote Similarity	NPC220173
0.5083	Remote Similarity	NPC81042
0.5078	Remote Similarity	NPC209550
0.5076	Remote Similarity	NPC473554
0.5047	Remote Similarity	NPC189142
0.5047	Remote Similarity	NPC77660
0.5046	Remote Similarity	NPC168584
0.5039	Remote Similarity	NPC474522

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4885
0.1-0.2	4206
0.2-0.3	50
0.3-0.4	3
0.4-0.5	6
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