NPASS Compound

Natural Product: NPC139571

Natural Product ID	NPC139571
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Isorhamnetin 3-O-(6''-O-E-Caffeoyl)-Beta-D-Galactopyranoside
IUPAC Name	[(2R,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444193
PubChem CID	10100672
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 74 78 0 0 0 0 0 0 0 0999 V2000 -7.5375 3.0918 0.8113 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4692 3.5286 1.5942 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3211 2.7636 1.6985 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1570 1.5599 1.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0068 0.7904 1.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0075 1.2759 1.9385 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1306 2.5058 2.6120 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2766 3.2488 2.4963 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4721 4.4776 3.1332 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9455 -0.5088 0.5174 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0978 -1.0784 0.1262 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1871 -2.2371 -0.4572 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4240 -2.7701 -0.8380 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5556 -3.9900 -1.4551 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8224 -4.4904 -1.8225 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4369 -4.7461 -1.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2032 -4.2464 -1.3607 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0795 -3.0123 -0.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8632 -2.4953 -0.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8199 -3.1547 -0.5991 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8283 -1.2351 0.2568 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5626 -0.7615 0.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8857 -0.1055 -0.5265 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0681 -0.9597 -0.9446 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3679 -0.7571 -0.7876 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9006 -1.4392 0.4892 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2645 -1.1648 0.5161 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1883 -1.5627 1.4355 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8323 -2.2784 2.3886 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6146 -1.1666 1.3446 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9992 -0.3964 0.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3412 0.0605 0.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3897 -0.2373 0.9197 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6697 0.2278 0.6663 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9093 1.0269 -0.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8527 1.3302 -1.2706 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6025 0.8635 -1.0054 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0687 2.1291 -2.3931 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1849 1.4894 -0.6996 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8641 0.6646 -0.7235 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7532 1.6276 -1.0969 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4506 1.2755 -0.2290 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4365 2.2135 -0.6254 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1742 2.9269 -0.9200 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3756 0.9936 0.5091 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0484 -4.9835 -1.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4880 3.5993 1.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7537 2.0071 0.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4437 3.3122 -0.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9533 1.1726 0.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0630 0.7551 2.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3319 2.8813 3.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3724 4.5937 3.5923 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2946 -2.1758 -0.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5788 -4.2658 -1.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5012 -5.7045 -2.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6635 0.0182 -1.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9903 -1.2774 -1.6051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7628 -2.5471 0.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3343 -1.1494 1.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3233 -1.4851 2.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1863 -0.1257 -0.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2355 -0.8514 1.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4967 0.0012 1.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7773 1.1087 -1.6615 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9413 2.5669 -2.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6150 2.2102 -0.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6525 0.8082 -1.4817 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5132 1.4677 -2.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1504 1.4499 0.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6188 2.1228 -1.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2158 3.4550 -1.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8670 1.6832 0.9999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0939 -5.9252 -1.9655 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 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 14 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 25 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 17 46 1 0 8 3 1 0 21 10 2 0 42 23 1 0 18 12 1 0 37 32 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 6 51 1 0 7 52 1 0 9 53 1 0 13 54 1 0 15 55 1 0 16 56 1 0 23 57 1 6 25 58 1 6 26 59 1 0 26 60 1 0 30 61 1 0 31 62 1 0 33 63 1 0 34 64 1 0 37 65 1 0 38 66 1 0 39 67 1 0 40 68 1 6 41 69 1 6 42 70 1 1 43 71 1 0 44 72 1 0 45 73 1 0 46 74 1 0 M END

Standard InCHIKey	WSOXPMMZVRFANO-OVIBHWRASA-N
Standard InCHI	InChI=1S/C31H28O15/c1-42-20-9-14(4-6-17(20)34)29-30(26(39)24-19(36)10-15(32)11-21(24)44-29)46-31-28(41)27(40)25(38)22(45-31)12-43-23(37)7-3-13-2-5-16(33)18(35)8-13/h2-11,22,25,27-28,31-36,38,40-41H,12H2,1H3/b7-3+/t22-,25+,27+,28-,31+/m1/s1
SMILES	COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(c(c2)O)O)[C@@H]([C@@H]([C@H]1O)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
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374974]
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	47.7	ug.mL-1	PMID[9599253]
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	15.3	ug.mL-1	PMID[18443129]

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 NPC139571 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	17316
0.1-0.2	27928
0.2-0.3	3478
0.3-0.4	710
0.4-0.5	208
0.5-0.6	150
0.6-0.7	35
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9149	High Similarity	NPC217520
0.8723	High Similarity	NPC214621
0.8723	High Similarity	NPC34267
0.8723	High Similarity	NPC81042
0.8081	Intermediate Similarity	NPC477895
0.8041	Intermediate Similarity	NPC223426
0.8021	Intermediate Similarity	NPC85751
0.8021	Intermediate Similarity	NPC19240
0.7979	Intermediate Similarity	NPC153755
0.7129	Intermediate Similarity	NPC476472
0.7129	Intermediate Similarity	NPC294815
0.7129	Intermediate Similarity	NPC16194
0.7115	Intermediate Similarity	NPC470416
0.7059	Intermediate Similarity	NPC36138
0.6847	Remote Similarity	NPC488079
0.6837	Remote Similarity	NPC609888
0.6804	Remote Similarity	NPC116864
0.6804	Remote Similarity	NPC244776
0.6771	Remote Similarity	NPC223747
0.6701	Remote Similarity	NPC203050
0.6701	Remote Similarity	NPC225434
0.6696	Remote Similarity	NPC21359
0.6696	Remote Similarity	NPC460984
0.6609	Remote Similarity	NPC25946
0.6577	Remote Similarity	NPC474093
0.6577	Remote Similarity	NPC104910
0.6569	Remote Similarity	NPC470125
0.6476	Remote Similarity	NPC477629
0.6449	Remote Similarity	NPC96605
0.6449	Remote Similarity	NPC280642
0.6404	Remote Similarity	NPC488078
0.6355	Remote Similarity	NPC218161
0.6311	Remote Similarity	NPC129264
0.6296	Remote Similarity	NPC603856
0.6286	Remote Similarity	NPC37668
0.6286	Remote Similarity	NPC270448
0.6239	Remote Similarity	NPC599948
0.6132	Remote Similarity	NPC473327
0.6117	Remote Similarity	NPC67326
0.6061	Remote Similarity	NPC175107
0.6058	Remote Similarity	NPC203259
0.6058	Remote Similarity	NPC33054
0.6058	Remote Similarity	NPC176740
0.6058	Remote Similarity	NPC471725
0.6058	Remote Similarity	NPC134532
0.6058	Remote Similarity	NPC156869
0.6058	Remote Similarity	NPC602582
0.6033	Remote Similarity	NPC473554
0.6019	Remote Similarity	NPC471079
0.5982	Remote Similarity	NPC480796
0.5982	Remote Similarity	NPC173837
0.5981	Remote Similarity	NPC104883
0.5981	Remote Similarity	NPC488679
0.5962	Remote Similarity	NPC173582
0.5962	Remote Similarity	NPC265885
0.5962	Remote Similarity	NPC181465
0.5962	Remote Similarity	NPC215710
0.5962	Remote Similarity	NPC473438
0.5962	Remote Similarity	NPC253788
0.5948	Remote Similarity	NPC470713
0.5946	Remote Similarity	NPC89052
0.5932	Remote Similarity	NPC241781
0.5897	Remote Similarity	NPC156785
0.5872	Remote Similarity	NPC471669
0.5841	Remote Similarity	NPC472993
0.5794	Remote Similarity	NPC296018
0.5794	Remote Similarity	NPC154741
0.5781	Remote Similarity	NPC475179
0.5781	Remote Similarity	NPC487501
0.5763	Remote Similarity	NPC162394
0.5743	Remote Similarity	NPC219904
0.5727	Remote Similarity	NPC80068
0.569	Remote Similarity	NPC470718
0.5686	Remote Similarity	NPC120099
0.566	Remote Similarity	NPC39834
0.5657	Remote Similarity	NPC127546
0.5657	Remote Similarity	NPC57625
0.5657	Remote Similarity	NPC173637
0.5657	Remote Similarity	NPC317489
0.5657	Remote Similarity	NPC223424
0.5657	Remote Similarity	NPC600591
0.5652	Remote Similarity	NPC470712
0.5644	Remote Similarity	NPC325555
0.5644	Remote Similarity	NPC226304
0.5636	Remote Similarity	NPC270675
0.5636	Remote Similarity	NPC195685
0.563	Remote Similarity	NPC474522
0.5625	Remote Similarity	NPC470450
0.56	Remote Similarity	NPC145038
0.56	Remote Similarity	NPC56077
0.56	Remote Similarity	NPC281131
0.56	Remote Similarity	NPC253662
0.56	Remote Similarity	NPC179950
0.56	Remote Similarity	NPC88789
0.56	Remote Similarity	NPC491374
0.5556	Remote Similarity	NPC111929
0.5556	Remote Similarity	NPC320283
0.5556	Remote Similarity	NPC41121
0.5534	Remote Similarity	NPC101026
0.5534	Remote Similarity	NPC488077
0.5526	Remote Similarity	NPC121703
0.5512	Remote Similarity	NPC487502
0.551	Remote Similarity	NPC157898
0.5505	Remote Similarity	NPC488074
0.5504	Remote Similarity	NPC97817
0.55	Remote Similarity	NPC77672
0.55	Remote Similarity	NPC133671
0.55	Remote Similarity	NPC135391
0.55	Remote Similarity	NPC78263
0.55	Remote Similarity	NPC250069
0.5495	Remote Similarity	NPC205824
0.549	Remote Similarity	NPC472459
0.5462	Remote Similarity	NPC487500
0.5446	Remote Similarity	NPC265530
0.5446	Remote Similarity	NPC220173
0.5439	Remote Similarity	NPC478277
0.5439	Remote Similarity	NPC478276
0.5439	Remote Similarity	NPC478275
0.5439	Remote Similarity	NPC92815
0.5437	Remote Similarity	NPC60735
0.5437	Remote Similarity	NPC26230
0.5431	Remote Similarity	NPC219043
0.5431	Remote Similarity	NPC292019
0.5431	Remote Similarity	NPC202908
0.5392	Remote Similarity	NPC291296
0.5385	Remote Similarity	NPC609478
0.5377	Remote Similarity	NPC4390
0.5366	Remote Similarity	NPC192539
0.5364	Remote Similarity	NPC488073
0.5364	Remote Similarity	NPC126784
0.5364	Remote Similarity	NPC241423
0.5357	Remote Similarity	NPC486577
0.5354	Remote Similarity	NPC276222
0.5354	Remote Similarity	NPC274618
0.5354	Remote Similarity	NPC118284
0.5354	Remote Similarity	NPC608147
0.5351	Remote Similarity	NPC472994
0.5345	Remote Similarity	NPC189564
0.5333	Remote Similarity	NPC206123
0.5328	Remote Similarity	NPC470720
0.5326	Remote Similarity	NPC279989
0.5304	Remote Similarity	NPC483765
0.53	Remote Similarity	NPC67037
0.53	Remote Similarity	NPC255615
0.5299	Remote Similarity	NPC482521
0.5294	Remote Similarity	NPC64305
0.5276	Remote Similarity	NPC275977
0.5273	Remote Similarity	NPC473571
0.5273	Remote Similarity	NPC110941
0.5263	Remote Similarity	NPC260504
0.5263	Remote Similarity	NPC89809
0.5263	Remote Similarity	NPC470445
0.5253	Remote Similarity	NPC54802
0.5253	Remote Similarity	NPC197304
0.5248	Remote Similarity	NPC135599
0.5248	Remote Similarity	NPC73855
0.5248	Remote Similarity	NPC113968
0.5248	Remote Similarity	NPC328940
0.5248	Remote Similarity	NPC277174
0.5248	Remote Similarity	NPC606877
0.5231	Remote Similarity	NPC249560
0.5221	Remote Similarity	NPC101399
0.5221	Remote Similarity	NPC221288
0.5221	Remote Similarity	NPC217822
0.5221	Remote Similarity	NPC11847
0.5221	Remote Similarity	NPC198938
0.5221	Remote Similarity	NPC194836
0.5221	Remote Similarity	NPC91493
0.5221	Remote Similarity	NPC605081
0.5217	Remote Similarity	NPC483767
0.5217	Remote Similarity	NPC470446
0.5217	Remote Similarity	NPC483769
0.5217	Remote Similarity	NPC483768
0.5217	Remote Similarity	NPC483766
0.52	Remote Similarity	NPC288084
0.5196	Remote Similarity	NPC19388
0.5196	Remote Similarity	NPC240431
0.5196	Remote Similarity	NPC55786
0.5194	Remote Similarity	NPC72554
0.5182	Remote Similarity	NPC133984
0.5175	Remote Similarity	NPC470447
0.5175	Remote Similarity	NPC135831
0.5143	Remote Similarity	NPC157816
0.5143	Remote Similarity	NPC159579
0.514	Remote Similarity	NPC488072
0.514	Remote Similarity	NPC476870
0.5133	Remote Similarity	NPC476620
0.513	Remote Similarity	NPC470449
0.5122	Remote Similarity	NPC488740
0.5122	Remote Similarity	NPC488736
0.5122	Remote Similarity	NPC488733
0.5122	Remote Similarity	NPC470717
0.5094	Remote Similarity	NPC197285
0.5085	Remote Similarity	NPC470451
0.5082	Remote Similarity	NPC488734
0.5082	Remote Similarity	NPC488735
0.5082	Remote Similarity	NPC488739
0.5082	Remote Similarity	NPC488732
0.5082	Remote Similarity	NPC488738

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC139571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4459
0.1-0.2	4630
0.2-0.3	47
0.3-0.4	10
0.4-0.5	3
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
0.6058	Remote Similarity	NPD6797	Phase 2

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